Intermediate changes

commit_hash:c4352485eb2978cb2b34e9c09ab3231db1290c81

20 files changed, 1563 insertions, 478 deletions

diff --git a/contrib/python/packaging/py3/.dist-info/METADATA b/contrib/python/packaging/py3/.dist-info/METADATA
index 10b290a6cd1..3200e601f97 100644
--- a/contrib/python/packaging/py3/.dist-info/METADATA
+++ b/contrib/python/packaging/py3/.dist-info/METADATA
@@ -1,14 +1,13 @@
 Metadata-Version: 2.4
 Name: packaging
-Version: 25.0
+Version: 26.0
 Summary: Core utilities for Python packages
 Author-email: Donald Stufft <[email protected]>
 Requires-Python: >=3.8
 Description-Content-Type: text/x-rst
+License-Expression: Apache-2.0 OR BSD-2-Clause
 Classifier: Development Status :: 5 - Production/Stable
 Classifier: Intended Audience :: Developers
-Classifier: License :: OSI Approved :: Apache Software License
-Classifier: License :: OSI Approved :: BSD License
 Classifier: Programming Language :: Python
 Classifier: Programming Language :: Python :: 3
 Classifier: Programming Language :: Python :: 3 :: Only
@@ -18,6 +17,7 @@ Classifier: Programming Language :: Python :: 3.10
 Classifier: Programming Language :: Python :: 3.11
 Classifier: Programming Language :: Python :: 3.12
 Classifier: Programming Language :: Python :: 3.13
+Classifier: Programming Language :: Python :: 3.14
 Classifier: Programming Language :: Python :: Implementation :: CPython
 Classifier: Programming Language :: Python :: Implementation :: PyPy
 Classifier: Typing :: Typed
@@ -42,7 +42,7 @@ or benefit greatly from having a single shared implementation (eg: :pep:`425`).
 .. end-intro
 
 The ``packaging`` project includes the following: version handling, specifiers,
-markers, requirements, tags, utilities.
+markers, requirements, tags, metadata, lockfiles, utilities.
 
 Documentation
 -------------
@@ -54,6 +54,8 @@ The `documentation`_ provides information and the API for the following:
 - Markers
 - Requirements
 - Tags
+- Metadata
+- Lockfiles
 - Utilities
 
 Installation
diff --git a/contrib/python/packaging/py3/README.rst b/contrib/python/packaging/py3/README.rst
index 4e01206a144..ba3fa462bf1 100644
--- a/contrib/python/packaging/py3/README.rst
+++ b/contrib/python/packaging/py3/README.rst
@@ -13,7 +13,7 @@ or benefit greatly from having a single shared implementation (eg: :pep:`425`).
 .. end-intro
 
 The ``packaging`` project includes the following: version handling, specifiers,
-markers, requirements, tags, utilities.
+markers, requirements, tags, metadata, lockfiles, utilities.
 
 Documentation
 -------------
@@ -25,6 +25,8 @@ The `documentation`_ provides information and the API for the following:
 - Markers
 - Requirements
 - Tags
+- Metadata
+- Lockfiles
 - Utilities
 
 Installation
diff --git a/contrib/python/packaging/py3/packaging/__init__.py b/contrib/python/packaging/py3/packaging/__init__.py
index d45c22cfd88..21695a74b51 100644
--- a/contrib/python/packaging/py3/packaging/__init__.py
+++ b/contrib/python/packaging/py3/packaging/__init__.py
@@ -6,7 +6,7 @@ __title__ = "packaging"
 __summary__ = "Core utilities for Python packages"
 __uri__ = "https://github.com/pypa/packaging"
 
-__version__ = "25.0"
+__version__ = "26.0"
 
 __author__ = "Donald Stufft and individual contributors"
 __email__ = "[email protected]"
diff --git a/contrib/python/packaging/py3/packaging/_elffile.py b/contrib/python/packaging/py3/packaging/_elffile.py
index 7a5afc33b0a..497b0645217 100644
--- a/contrib/python/packaging/py3/packaging/_elffile.py
+++ b/contrib/python/packaging/py3/packaging/_elffile.py
@@ -4,7 +4,6 @@ ELF file parser.
 This provides a class ``ELFFile`` that parses an ELF executable in a similar
 interface to ``ZipFile``. Only the read interface is implemented.
 
-Based on: https://gist.github.com/lyssdod/f51579ae8d93c8657a5564aefc2ffbca
 ELF header: https://refspecs.linuxfoundation.org/elf/gabi4+/ch4.eheader.html
 """
 
diff --git a/contrib/python/packaging/py3/packaging/_manylinux.py b/contrib/python/packaging/py3/packaging/_manylinux.py
index 95f55762e86..0e79e8a882b 100644
--- a/contrib/python/packaging/py3/packaging/_manylinux.py
+++ b/contrib/python/packaging/py3/packaging/_manylinux.py
@@ -15,6 +15,16 @@ EF_ARM_ABIMASK = 0xFF000000
 EF_ARM_ABI_VER5 = 0x05000000
 EF_ARM_ABI_FLOAT_HARD = 0x00000400
 
+_ALLOWED_ARCHS = {
+    "x86_64",
+    "aarch64",
+    "ppc64",
+    "ppc64le",
+    "s390x",
+    "loongarch64",
+    "riscv64",
+}
+
 
 # `os.PathLike` not a generic type until Python 3.9, so sticking with `str`
 # as the type for `path` until then.
@@ -57,16 +67,7 @@ def _have_compatible_abi(executable: str, archs: Sequence[str]) -> bool:
         return _is_linux_armhf(executable)
     if "i686" in archs:
         return _is_linux_i686(executable)
-    allowed_archs = {
-        "x86_64",
-        "aarch64",
-        "ppc64",
-        "ppc64le",
-        "s390x",
-        "loongarch64",
-        "riscv64",
-    }
-    return any(arch in allowed_archs for arch in archs)
+    return any(arch in _ALLOWED_ARCHS for arch in archs)
 
 
 # If glibc ever changes its major version, we need to know what the last
@@ -106,7 +107,7 @@ def _glibc_version_string_ctypes() -> str | None:
     Fallback implementation of glibc_version_string using ctypes.
     """
     try:
-        import ctypes
+        import ctypes  # noqa: PLC0415
     except ImportError:
         return None
 
@@ -150,7 +151,7 @@ def _glibc_version_string() -> str | None:
     return _glibc_version_string_confstr() or _glibc_version_string_ctypes()
 
 
-def _parse_glibc_version(version_str: str) -> tuple[int, int]:
+def _parse_glibc_version(version_str: str) -> _GLibCVersion:
     """Parse glibc version.
 
     We use a regexp instead of str.split because we want to discard any
@@ -165,15 +166,15 @@ def _parse_glibc_version(version_str: str) -> tuple[int, int]:
             RuntimeWarning,
             stacklevel=2,
         )
-        return -1, -1
-    return int(m.group("major")), int(m.group("minor"))
+        return _GLibCVersion(-1, -1)
+    return _GLibCVersion(int(m.group("major")), int(m.group("minor")))
 
 
 @functools.lru_cache
-def _get_glibc_version() -> tuple[int, int]:
+def _get_glibc_version() -> _GLibCVersion:
     version_str = _glibc_version_string()
     if version_str is None:
-        return (-1, -1)
+        return _GLibCVersion(-1, -1)
     return _parse_glibc_version(version_str)
 
 
@@ -184,7 +185,7 @@ def _is_compatible(arch: str, version: _GLibCVersion) -> bool:
         return False
     # Check for presence of _manylinux module.
     try:
-        import _manylinux
+        import _manylinux  # noqa: PLC0415
     except ImportError:
         return True
     if hasattr(_manylinux, "manylinux_compatible"):
@@ -192,25 +193,26 @@ def _is_compatible(arch: str, version: _GLibCVersion) -> bool:
         if result is not None:
             return bool(result)
         return True
-    if version == _GLibCVersion(2, 5):
-        if hasattr(_manylinux, "manylinux1_compatible"):
-            return bool(_manylinux.manylinux1_compatible)
-    if version == _GLibCVersion(2, 12):
-        if hasattr(_manylinux, "manylinux2010_compatible"):
-            return bool(_manylinux.manylinux2010_compatible)
-    if version == _GLibCVersion(2, 17):
-        if hasattr(_manylinux, "manylinux2014_compatible"):
-            return bool(_manylinux.manylinux2014_compatible)
+    if version == _GLibCVersion(2, 5) and hasattr(_manylinux, "manylinux1_compatible"):
+        return bool(_manylinux.manylinux1_compatible)
+    if version == _GLibCVersion(2, 12) and hasattr(
+        _manylinux, "manylinux2010_compatible"
+    ):
+        return bool(_manylinux.manylinux2010_compatible)
+    if version == _GLibCVersion(2, 17) and hasattr(
+        _manylinux, "manylinux2014_compatible"
+    ):
+        return bool(_manylinux.manylinux2014_compatible)
     return True
 
 
-_LEGACY_MANYLINUX_MAP = {
+_LEGACY_MANYLINUX_MAP: dict[_GLibCVersion, str] = {
     # CentOS 7 w/ glibc 2.17 (PEP 599)
-    (2, 17): "manylinux2014",
+    _GLibCVersion(2, 17): "manylinux2014",
     # CentOS 6 w/ glibc 2.12 (PEP 571)
-    (2, 12): "manylinux2010",
+    _GLibCVersion(2, 12): "manylinux2010",
     # CentOS 5 w/ glibc 2.5 (PEP 513)
-    (2, 5): "manylinux1",
+    _GLibCVersion(2, 5): "manylinux1",
 }
 
 
@@ -252,11 +254,9 @@ def platform_tags(archs: Sequence[str]) -> Iterator[str]:
                 min_minor = -1
             for glibc_minor in range(glibc_max.minor, min_minor, -1):
                 glibc_version = _GLibCVersion(glibc_max.major, glibc_minor)
-                tag = "manylinux_{}_{}".format(*glibc_version)
                 if _is_compatible(arch, glibc_version):
-                    yield f"{tag}_{arch}"
-                # Handle the legacy manylinux1, manylinux2010, manylinux2014 tags.
-                if glibc_version in _LEGACY_MANYLINUX_MAP:
-                    legacy_tag = _LEGACY_MANYLINUX_MAP[glibc_version]
-                    if _is_compatible(arch, glibc_version):
+                    yield "manylinux_{}_{}_{}".format(*glibc_version, arch)
+
+                    # Handle the legacy manylinux1, manylinux2010, manylinux2014 tags.
+                    if legacy_tag := _LEGACY_MANYLINUX_MAP.get(glibc_version):
                         yield f"{legacy_tag}_{arch}"
diff --git a/contrib/python/packaging/py3/packaging/_musllinux.py b/contrib/python/packaging/py3/packaging/_musllinux.py
index d2bf30b5631..4e8116a79ca 100644
--- a/contrib/python/packaging/py3/packaging/_musllinux.py
+++ b/contrib/python/packaging/py3/packaging/_musllinux.py
@@ -49,7 +49,7 @@ def _get_musl_version(executable: str) -> _MuslVersion | None:
         return None
     if ld is None or "musl" not in ld:
         return None
-    proc = subprocess.run([ld], stderr=subprocess.PIPE, text=True)
+    proc = subprocess.run([ld], check=False, stderr=subprocess.PIPE, text=True)
     return _parse_musl_version(proc.stderr)
 
 
diff --git a/contrib/python/packaging/py3/packaging/_parser.py b/contrib/python/packaging/py3/packaging/_parser.py
index 0007c0aa64a..f6c1f5cd226 100644
--- a/contrib/python/packaging/py3/packaging/_parser.py
+++ b/contrib/python/packaging/py3/packaging/_parser.py
@@ -7,12 +7,14 @@ the implementation.
 from __future__ import annotations
 
 import ast
-from typing import NamedTuple, Sequence, Tuple, Union
+from typing import List, Literal, NamedTuple, Sequence, Tuple, Union
 
 from ._tokenizer import DEFAULT_RULES, Tokenizer
 
 
 class Node:
+    __slots__ = ("value",)
+
     def __init__(self, value: str) -> None:
         self.value = value
 
@@ -20,31 +22,38 @@ class Node:
         return self.value
 
     def __repr__(self) -> str:
-        return f"<{self.__class__.__name__}('{self}')>"
+        return f"<{self.__class__.__name__}({self.value!r})>"
 
     def serialize(self) -> str:
         raise NotImplementedError
 
 
 class Variable(Node):
+    __slots__ = ()
+
     def serialize(self) -> str:
         return str(self)
 
 
 class Value(Node):
+    __slots__ = ()
+
     def serialize(self) -> str:
         return f'"{self}"'
 
 
 class Op(Node):
+    __slots__ = ()
+
     def serialize(self) -> str:
         return str(self)
 
 
+MarkerLogical = Literal["and", "or"]
 MarkerVar = Union[Variable, Value]
 MarkerItem = Tuple[MarkerVar, Op, MarkerVar]
 MarkerAtom = Union[MarkerItem, Sequence["MarkerAtom"]]
-MarkerList = Sequence[Union["MarkerList", MarkerAtom, str]]
+MarkerList = List[Union["MarkerList", MarkerAtom, MarkerLogical]]
 
 
 class ParsedRequirement(NamedTuple):
@@ -111,7 +120,9 @@ def _parse_requirement_details(
             return (url, specifier, marker)
 
         marker = _parse_requirement_marker(
-            tokenizer, span_start=url_start, after="URL and whitespace"
+            tokenizer,
+            span_start=url_start,
+            expected="semicolon (after URL and whitespace)",
         )
     else:
         specifier_start = tokenizer.position
@@ -124,10 +135,10 @@ def _parse_requirement_details(
         marker = _parse_requirement_marker(
             tokenizer,
             span_start=specifier_start,
-            after=(
-                "version specifier"
+            expected=(
+                "comma (within version specifier), semicolon (after version specifier)"
                 if specifier
-                else "name and no valid version specifier"
+                else "semicolon (after name with no version specifier)"
             ),
         )
 
@@ -135,7 +146,7 @@ def _parse_requirement_details(
 
 
 def _parse_requirement_marker(
-    tokenizer: Tokenizer, *, span_start: int, after: str
+    tokenizer: Tokenizer, *, span_start: int, expected: str
 ) -> MarkerList:
     """
     requirement_marker = SEMICOLON marker WS?
@@ -143,8 +154,9 @@ def _parse_requirement_marker(
 
     if not tokenizer.check("SEMICOLON"):
         tokenizer.raise_syntax_error(
-            f"Expected end or semicolon (after {after})",
+            f"Expected {expected} or end",
             span_start=span_start,
+            span_end=None,
         )
     tokenizer.read()
 
@@ -307,7 +319,7 @@ def _parse_marker_item(tokenizer: Tokenizer) -> MarkerItem:
     return (marker_var_left, marker_op, marker_var_right)
 
 
-def _parse_marker_var(tokenizer: Tokenizer) -> MarkerVar:
+def _parse_marker_var(tokenizer: Tokenizer) -> MarkerVar:  # noqa: RET503
     """
     marker_var = VARIABLE | QUOTED_STRING
     """
diff --git a/contrib/python/packaging/py3/packaging/_structures.py b/contrib/python/packaging/py3/packaging/_structures.py
index 90a6465f968..225e2eee012 100644
--- a/contrib/python/packaging/py3/packaging/_structures.py
+++ b/contrib/python/packaging/py3/packaging/_structures.py
@@ -2,8 +2,13 @@
 # 2.0, and the BSD License. See the LICENSE file in the root of this repository
 # for complete details.
 
+import typing
 
+
[email protected]
 class InfinityType:
+    __slots__ = ()
+
     def __repr__(self) -> str:
         return "Infinity"
 
@@ -32,7 +37,10 @@ class InfinityType:
 Infinity = InfinityType()
 
 
[email protected]
 class NegativeInfinityType:
+    __slots__ = ()
+
     def __repr__(self) -> str:
         return "-Infinity"
 
diff --git a/contrib/python/packaging/py3/packaging/_tokenizer.py b/contrib/python/packaging/py3/packaging/_tokenizer.py
index d28a9b6cf5d..e6d20dd3f56 100644
--- a/contrib/python/packaging/py3/packaging/_tokenizer.py
+++ b/contrib/python/packaging/py3/packaging/_tokenizer.py
@@ -3,7 +3,7 @@ from __future__ import annotations
 import contextlib
 import re
 from dataclasses import dataclass
-from typing import Iterator, NoReturn
+from typing import Generator, Mapping, NoReturn
 
 from .specifiers import Specifier
 
@@ -33,16 +33,16 @@ class ParserSyntaxError(Exception):
 
     def __str__(self) -> str:
         marker = " " * self.span[0] + "~" * (self.span[1] - self.span[0]) + "^"
-        return "\n    ".join([self.message, self.source, marker])
+        return f"{self.message}\n    {self.source}\n    {marker}"
 
 
-DEFAULT_RULES: dict[str, str | re.Pattern[str]] = {
-    "LEFT_PARENTHESIS": r"\(",
-    "RIGHT_PARENTHESIS": r"\)",
-    "LEFT_BRACKET": r"\[",
-    "RIGHT_BRACKET": r"\]",
-    "SEMICOLON": r";",
-    "COMMA": r",",
+DEFAULT_RULES: dict[str, re.Pattern[str]] = {
+    "LEFT_PARENTHESIS": re.compile(r"\("),
+    "RIGHT_PARENTHESIS": re.compile(r"\)"),
+    "LEFT_BRACKET": re.compile(r"\["),
+    "RIGHT_BRACKET": re.compile(r"\]"),
+    "SEMICOLON": re.compile(r";"),
+    "COMMA": re.compile(r","),
     "QUOTED_STRING": re.compile(
         r"""
             (
@@ -53,10 +53,10 @@ DEFAULT_RULES: dict[str, str | re.Pattern[str]] = {
         """,
         re.VERBOSE,
     ),
-    "OP": r"(===|==|~=|!=|<=|>=|<|>)",
-    "BOOLOP": r"\b(or|and)\b",
-    "IN": r"\bin\b",
-    "NOT": r"\bnot\b",
+    "OP": re.compile(r"(===|==|~=|!=|<=|>=|<|>)"),
+    "BOOLOP": re.compile(r"\b(or|and)\b"),
+    "IN": re.compile(r"\bin\b"),
+    "NOT": re.compile(r"\bnot\b"),
     "VARIABLE": re.compile(
         r"""
             \b(
@@ -78,13 +78,13 @@ DEFAULT_RULES: dict[str, str | re.Pattern[str]] = {
         Specifier._operator_regex_str + Specifier._version_regex_str,
         re.VERBOSE | re.IGNORECASE,
     ),
-    "AT": r"\@",
-    "URL": r"[^ \t]+",
-    "IDENTIFIER": r"\b[a-zA-Z0-9][a-zA-Z0-9._-]*\b",
-    "VERSION_PREFIX_TRAIL": r"\.\*",
-    "VERSION_LOCAL_LABEL_TRAIL": r"\+[a-z0-9]+(?:[-_\.][a-z0-9]+)*",
-    "WS": r"[ \t]+",
-    "END": r"$",
+    "AT": re.compile(r"\@"),
+    "URL": re.compile(r"[^ \t]+"),
+    "IDENTIFIER": re.compile(r"\b[a-zA-Z0-9][a-zA-Z0-9._-]*\b"),
+    "VERSION_PREFIX_TRAIL": re.compile(r"\.\*"),
+    "VERSION_LOCAL_LABEL_TRAIL": re.compile(r"\+[a-z0-9]+(?:[-_\.][a-z0-9]+)*"),
+    "WS": re.compile(r"[ \t]+"),
+    "END": re.compile(r"$"),
 }
 
 
@@ -99,12 +99,10 @@ class Tokenizer:
         self,
         source: str,
         *,
-        rules: dict[str, str | re.Pattern[str]],
+        rules: Mapping[str, re.Pattern[str]],
     ) -> None:
         self.source = source
-        self.rules: dict[str, re.Pattern[str]] = {
-            name: re.compile(pattern) for name, pattern in rules.items()
-        }
+        self.rules = rules
         self.next_token: Token | None = None
         self.position = 0
 
@@ -174,7 +172,7 @@ class Tokenizer:
     @contextlib.contextmanager
     def enclosing_tokens(
         self, open_token: str, close_token: str, *, around: str
-    ) -> Iterator[None]:
+    ) -> Generator[None, None, None]:
         if self.check(open_token):
             open_position = self.position
             self.read()
diff --git a/contrib/python/packaging/py3/packaging/licenses/__init__.py b/contrib/python/packaging/py3/packaging/licenses/__init__.py
index 6f7f9e6289d..335b275fa75 100644
--- a/contrib/python/packaging/py3/packaging/licenses/__init__.py
+++ b/contrib/python/packaging/py3/packaging/licenses/__init__.py
@@ -34,7 +34,7 @@ from __future__ import annotations
 import re
 from typing import NewType, cast
 
-from packaging.licenses._spdx import EXCEPTIONS, LICENSES
+from ._spdx import EXCEPTIONS, LICENSES
 
 __all__ = [
     "InvalidLicenseExpression",
@@ -80,16 +80,21 @@ def canonicalize_license_expression(
 
     tokens = license_expression.split()
 
-    # Rather than implementing boolean logic, we create an expression that Python can
-    # parse. Everything that is not involved with the grammar itself is treated as
-    # `False` and the expression should evaluate as such.
+    # Rather than implementing a parenthesis/boolean logic parser, create an
+    # expression that Python can parse. Everything that is not involved with the
+    # grammar itself is replaced with the placeholder `False` and the resultant
+    # expression should become a valid Python expression.
     python_tokens = []
     for token in tokens:
         if token not in {"or", "and", "with", "(", ")"}:
             python_tokens.append("False")
         elif token == "with":
             python_tokens.append("or")
-        elif token == "(" and python_tokens and python_tokens[-1] not in {"or", "and"}:
+        elif (
+            token == "("
+            and python_tokens
+            and python_tokens[-1] not in {"or", "and", "("}
+        ) or (token == ")" and python_tokens and python_tokens[-1] == "("):
             message = f"Invalid license expression: {raw_license_expression!r}"
             raise InvalidLicenseExpression(message)
         else:
@@ -97,11 +102,8 @@ def canonicalize_license_expression(
 
     python_expression = " ".join(python_tokens)
     try:
-        invalid = eval(python_expression, globals(), locals())
-    except Exception:
-        invalid = True
-
-    if invalid is not False:
+        compile(python_expression, "", "eval")
+    except SyntaxError:
         message = f"Invalid license expression: {raw_license_expression!r}"
         raise InvalidLicenseExpression(message) from None
 
@@ -140,6 +142,6 @@ def canonicalize_license_expression(
     normalized_expression = " ".join(normalized_tokens)
 
     return cast(
-        NormalizedLicenseExpression,
+        "NormalizedLicenseExpression",
         normalized_expression.replace("( ", "(").replace(" )", ")"),
     )
diff --git a/contrib/python/packaging/py3/packaging/licenses/_spdx.py b/contrib/python/packaging/py3/packaging/licenses/_spdx.py
index eac22276a34..a277af28220 100644
--- a/contrib/python/packaging/py3/packaging/licenses/_spdx.py
+++ b/contrib/python/packaging/py3/packaging/licenses/_spdx.py
@@ -12,7 +12,7 @@ class SPDXException(TypedDict):
     deprecated: bool
 
 
-VERSION = '3.25.0'
+VERSION = '3.27.0'
 
 LICENSES: dict[str, SPDXLicense] = {
     '0bsd': {'id': '0BSD', 'deprecated': False},
@@ -46,6 +46,7 @@ LICENSES: dict[str, SPDXLicense] = {
     'antlr-pd': {'id': 'ANTLR-PD', 'deprecated': False},
     'antlr-pd-fallback': {'id': 'ANTLR-PD-fallback', 'deprecated': False},
     'any-osi': {'id': 'any-OSI', 'deprecated': False},
+    'any-osi-perl-modules': {'id': 'any-OSI-perl-modules', 'deprecated': False},
     'apache-1.0': {'id': 'Apache-1.0', 'deprecated': False},
     'apache-1.1': {'id': 'Apache-1.1', 'deprecated': False},
     'apache-2.0': {'id': 'Apache-2.0', 'deprecated': False},
@@ -61,6 +62,8 @@ LICENSES: dict[str, SPDXLicense] = {
     'artistic-1.0-cl8': {'id': 'Artistic-1.0-cl8', 'deprecated': False},
     'artistic-1.0-perl': {'id': 'Artistic-1.0-Perl', 'deprecated': False},
     'artistic-2.0': {'id': 'Artistic-2.0', 'deprecated': False},
+    'artistic-dist': {'id': 'Artistic-dist', 'deprecated': False},
+    'aspell-ru': {'id': 'Aspell-RU', 'deprecated': False},
     'aswf-digital-assets-1.0': {'id': 'ASWF-Digital-Assets-1.0', 'deprecated': False},
     'aswf-digital-assets-1.1': {'id': 'ASWF-Digital-Assets-1.1', 'deprecated': False},
     'baekmuk': {'id': 'Baekmuk', 'deprecated': False},
@@ -75,6 +78,7 @@ LICENSES: dict[str, SPDXLicense] = {
     'blessing': {'id': 'blessing', 'deprecated': False},
     'blueoak-1.0.0': {'id': 'BlueOak-1.0.0', 'deprecated': False},
     'boehm-gc': {'id': 'Boehm-GC', 'deprecated': False},
+    'boehm-gc-without-fee': {'id': 'Boehm-GC-without-fee', 'deprecated': False},
     'borceux': {'id': 'Borceux', 'deprecated': False},
     'brian-gladman-2-clause': {'id': 'Brian-Gladman-2-Clause', 'deprecated': False},
     'brian-gladman-3-clause': {'id': 'Brian-Gladman-3-Clause', 'deprecated': False},
@@ -85,6 +89,7 @@ LICENSES: dict[str, SPDXLicense] = {
     'bsd-2-clause-freebsd': {'id': 'BSD-2-Clause-FreeBSD', 'deprecated': True},
     'bsd-2-clause-netbsd': {'id': 'BSD-2-Clause-NetBSD', 'deprecated': True},
     'bsd-2-clause-patent': {'id': 'BSD-2-Clause-Patent', 'deprecated': False},
+    'bsd-2-clause-pkgconf-disclaimer': {'id': 'BSD-2-Clause-pkgconf-disclaimer', 'deprecated': False},
     'bsd-2-clause-views': {'id': 'BSD-2-Clause-Views', 'deprecated': False},
     'bsd-3-clause': {'id': 'BSD-3-Clause', 'deprecated': False},
     'bsd-3-clause-acpica': {'id': 'BSD-3-Clause-acpica', 'deprecated': False},
@@ -176,6 +181,8 @@ LICENSES: dict[str, SPDXLicense] = {
     'cc-by-sa-3.0-igo': {'id': 'CC-BY-SA-3.0-IGO', 'deprecated': False},
     'cc-by-sa-4.0': {'id': 'CC-BY-SA-4.0', 'deprecated': False},
     'cc-pddc': {'id': 'CC-PDDC', 'deprecated': False},
+    'cc-pdm-1.0': {'id': 'CC-PDM-1.0', 'deprecated': False},
+    'cc-sa-1.0': {'id': 'CC-SA-1.0', 'deprecated': False},
     'cc0-1.0': {'id': 'CC0-1.0', 'deprecated': False},
     'cddl-1.0': {'id': 'CDDL-1.0', 'deprecated': False},
     'cddl-1.1': {'id': 'CDDL-1.1', 'deprecated': False},
@@ -215,6 +222,7 @@ LICENSES: dict[str, SPDXLicense] = {
     'cpol-1.02': {'id': 'CPOL-1.02', 'deprecated': False},
     'cronyx': {'id': 'Cronyx', 'deprecated': False},
     'crossword': {'id': 'Crossword', 'deprecated': False},
+    'cryptoswift': {'id': 'CryptoSwift', 'deprecated': False},
     'crystalstacker': {'id': 'CrystalStacker', 'deprecated': False},
     'cua-opl-1.0': {'id': 'CUA-OPL-1.0', 'deprecated': False},
     'cube': {'id': 'Cube', 'deprecated': False},
@@ -226,7 +234,9 @@ LICENSES: dict[str, SPDXLicense] = {
     'dl-de-by-2.0': {'id': 'DL-DE-BY-2.0', 'deprecated': False},
     'dl-de-zero-2.0': {'id': 'DL-DE-ZERO-2.0', 'deprecated': False},
     'doc': {'id': 'DOC', 'deprecated': False},
+    'docbook-dtd': {'id': 'DocBook-DTD', 'deprecated': False},
     'docbook-schema': {'id': 'DocBook-Schema', 'deprecated': False},
+    'docbook-stylesheet': {'id': 'DocBook-Stylesheet', 'deprecated': False},
     'docbook-xml': {'id': 'DocBook-XML', 'deprecated': False},
     'dotseqn': {'id': 'Dotseqn', 'deprecated': False},
     'drl-1.0': {'id': 'DRL-1.0', 'deprecated': False},
@@ -263,12 +273,17 @@ LICENSES: dict[str, SPDXLicense] = {
     'fsfap-no-warranty-disclaimer': {'id': 'FSFAP-no-warranty-disclaimer', 'deprecated': False},
     'fsful': {'id': 'FSFUL', 'deprecated': False},
     'fsfullr': {'id': 'FSFULLR', 'deprecated': False},
+    'fsfullrsd': {'id': 'FSFULLRSD', 'deprecated': False},
     'fsfullrwd': {'id': 'FSFULLRWD', 'deprecated': False},
+    'fsl-1.1-alv2': {'id': 'FSL-1.1-ALv2', 'deprecated': False},
+    'fsl-1.1-mit': {'id': 'FSL-1.1-MIT', 'deprecated': False},
     'ftl': {'id': 'FTL', 'deprecated': False},
     'furuseth': {'id': 'Furuseth', 'deprecated': False},
     'fwlw': {'id': 'fwlw', 'deprecated': False},
+    'game-programming-gems': {'id': 'Game-Programming-Gems', 'deprecated': False},
     'gcr-docs': {'id': 'GCR-docs', 'deprecated': False},
     'gd': {'id': 'GD', 'deprecated': False},
+    'generic-xts': {'id': 'generic-xts', 'deprecated': False},
     'gfdl-1.1': {'id': 'GFDL-1.1', 'deprecated': True},
     'gfdl-1.1-invariants-only': {'id': 'GFDL-1.1-invariants-only', 'deprecated': False},
     'gfdl-1.1-invariants-or-later': {'id': 'GFDL-1.1-invariants-or-later', 'deprecated': False},
@@ -320,6 +335,7 @@ LICENSES: dict[str, SPDXLicense] = {
     'gtkbook': {'id': 'gtkbook', 'deprecated': False},
     'gutmann': {'id': 'Gutmann', 'deprecated': False},
     'haskellreport': {'id': 'HaskellReport', 'deprecated': False},
+    'hdf5': {'id': 'HDF5', 'deprecated': False},
     'hdparm': {'id': 'hdparm', 'deprecated': False},
     'hidapi': {'id': 'HIDAPI', 'deprecated': False},
     'hippocratic-2.1': {'id': 'Hippocratic-2.1', 'deprecated': False},
@@ -360,6 +376,7 @@ LICENSES: dict[str, SPDXLicense] = {
     'imlib2': {'id': 'Imlib2', 'deprecated': False},
     'info-zip': {'id': 'Info-ZIP', 'deprecated': False},
     'inner-net-2.0': {'id': 'Inner-Net-2.0', 'deprecated': False},
+    'innosetup': {'id': 'InnoSetup', 'deprecated': False},
     'intel': {'id': 'Intel', 'deprecated': False},
     'intel-acpi': {'id': 'Intel-ACPI', 'deprecated': False},
     'interbase-1.0': {'id': 'Interbase-1.0', 'deprecated': False},
@@ -369,6 +386,7 @@ LICENSES: dict[str, SPDXLicense] = {
     'isc-veillard': {'id': 'ISC-Veillard', 'deprecated': False},
     'jam': {'id': 'Jam', 'deprecated': False},
     'jasper-2.0': {'id': 'JasPer-2.0', 'deprecated': False},
+    'jove': {'id': 'jove', 'deprecated': False},
     'jpl-image': {'id': 'JPL-image', 'deprecated': False},
     'jpnic': {'id': 'JPNIC', 'deprecated': False},
     'json': {'id': 'JSON', 'deprecated': False},
@@ -394,6 +412,7 @@ LICENSES: dict[str, SPDXLicense] = {
     'lgpl-3.0-or-later': {'id': 'LGPL-3.0-or-later', 'deprecated': False},
     'lgpllr': {'id': 'LGPLLR', 'deprecated': False},
     'libpng': {'id': 'Libpng', 'deprecated': False},
+    'libpng-1.6.35': {'id': 'libpng-1.6.35', 'deprecated': False},
     'libpng-2.0': {'id': 'libpng-2.0', 'deprecated': False},
     'libselinux-1.0': {'id': 'libselinux-1.0', 'deprecated': False},
     'libtiff': {'id': 'libtiff', 'deprecated': False},
@@ -424,14 +443,17 @@ LICENSES: dict[str, SPDXLicense] = {
     'magaz': {'id': 'magaz', 'deprecated': False},
     'mailprio': {'id': 'mailprio', 'deprecated': False},
     'makeindex': {'id': 'MakeIndex', 'deprecated': False},
+    'man2html': {'id': 'man2html', 'deprecated': False},
     'martin-birgmeier': {'id': 'Martin-Birgmeier', 'deprecated': False},
     'mcphee-slideshow': {'id': 'McPhee-slideshow', 'deprecated': False},
     'metamail': {'id': 'metamail', 'deprecated': False},
     'minpack': {'id': 'Minpack', 'deprecated': False},
+    'mips': {'id': 'MIPS', 'deprecated': False},
     'miros': {'id': 'MirOS', 'deprecated': False},
     'mit': {'id': 'MIT', 'deprecated': False},
     'mit-0': {'id': 'MIT-0', 'deprecated': False},
     'mit-advertising': {'id': 'MIT-advertising', 'deprecated': False},
+    'mit-click': {'id': 'MIT-Click', 'deprecated': False},
     'mit-cmu': {'id': 'MIT-CMU', 'deprecated': False},
     'mit-enna': {'id': 'MIT-enna', 'deprecated': False},
     'mit-feh': {'id': 'MIT-feh', 'deprecated': False},
@@ -472,6 +494,7 @@ LICENSES: dict[str, SPDXLicense] = {
     'netcdf': {'id': 'NetCDF', 'deprecated': False},
     'newsletr': {'id': 'Newsletr', 'deprecated': False},
     'ngpl': {'id': 'NGPL', 'deprecated': False},
+    'ngrep': {'id': 'ngrep', 'deprecated': False},
     'nicta-1.0': {'id': 'NICTA-1.0', 'deprecated': False},
     'nist-pd': {'id': 'NIST-PD', 'deprecated': False},
     'nist-pd-fallback': {'id': 'NIST-PD-fallback', 'deprecated': False},
@@ -486,6 +509,7 @@ LICENSES: dict[str, SPDXLicense] = {
     'npl-1.1': {'id': 'NPL-1.1', 'deprecated': False},
     'nposl-3.0': {'id': 'NPOSL-3.0', 'deprecated': False},
     'nrl': {'id': 'NRL', 'deprecated': False},
+    'ntia-pd': {'id': 'NTIA-PD', 'deprecated': False},
     'ntp': {'id': 'NTP', 'deprecated': False},
     'ntp-0': {'id': 'NTP-0', 'deprecated': False},
     'nunit': {'id': 'Nunit', 'deprecated': True},
@@ -580,6 +604,7 @@ LICENSES: dict[str, SPDXLicense] = {
     'schemereport': {'id': 'SchemeReport', 'deprecated': False},
     'sendmail': {'id': 'Sendmail', 'deprecated': False},
     'sendmail-8.23': {'id': 'Sendmail-8.23', 'deprecated': False},
+    'sendmail-open-source-1.1': {'id': 'Sendmail-Open-Source-1.1', 'deprecated': False},
     'sgi-b-1.0': {'id': 'SGI-B-1.0', 'deprecated': False},
     'sgi-b-1.1': {'id': 'SGI-B-1.1', 'deprecated': False},
     'sgi-b-2.0': {'id': 'SGI-B-2.0', 'deprecated': False},
@@ -592,10 +617,12 @@ LICENSES: dict[str, SPDXLicense] = {
     'sissl-1.2': {'id': 'SISSL-1.2', 'deprecated': False},
     'sl': {'id': 'SL', 'deprecated': False},
     'sleepycat': {'id': 'Sleepycat', 'deprecated': False},
+    'smail-gpl': {'id': 'SMAIL-GPL', 'deprecated': False},
     'smlnj': {'id': 'SMLNJ', 'deprecated': False},
     'smppl': {'id': 'SMPPL', 'deprecated': False},
     'snia': {'id': 'SNIA', 'deprecated': False},
     'snprintf': {'id': 'snprintf', 'deprecated': False},
+    'sofa': {'id': 'SOFA', 'deprecated': False},
     'softsurfer': {'id': 'softSurfer', 'deprecated': False},
     'soundex': {'id': 'Soundex', 'deprecated': False},
     'spencer-86': {'id': 'Spencer-86', 'deprecated': False},
@@ -609,6 +636,7 @@ LICENSES: dict[str, SPDXLicense] = {
     'sspl-1.0': {'id': 'SSPL-1.0', 'deprecated': False},
     'standardml-nj': {'id': 'StandardML-NJ', 'deprecated': True},
     'sugarcrm-1.1.3': {'id': 'SugarCRM-1.1.3', 'deprecated': False},
+    'sul-1.0': {'id': 'SUL-1.0', 'deprecated': False},
     'sun-ppp': {'id': 'Sun-PPP', 'deprecated': False},
     'sun-ppp-2000': {'id': 'Sun-PPP-2000', 'deprecated': False},
     'sunpro': {'id': 'SunPro', 'deprecated': False},
@@ -620,12 +648,14 @@ LICENSES: dict[str, SPDXLicense] = {
     'tcp-wrappers': {'id': 'TCP-wrappers', 'deprecated': False},
     'termreadkey': {'id': 'TermReadKey', 'deprecated': False},
     'tgppl-1.0': {'id': 'TGPPL-1.0', 'deprecated': False},
+    'thirdeye': {'id': 'ThirdEye', 'deprecated': False},
     'threeparttable': {'id': 'threeparttable', 'deprecated': False},
     'tmate': {'id': 'TMate', 'deprecated': False},
     'torque-1.1': {'id': 'TORQUE-1.1', 'deprecated': False},
     'tosl': {'id': 'TOSL', 'deprecated': False},
     'tpdl': {'id': 'TPDL', 'deprecated': False},
     'tpl-1.0': {'id': 'TPL-1.0', 'deprecated': False},
+    'trustedqsl': {'id': 'TrustedQSL', 'deprecated': False},
     'ttwl': {'id': 'TTWL', 'deprecated': False},
     'ttyp0': {'id': 'TTYP0', 'deprecated': False},
     'tu-berlin-1.0': {'id': 'TU-Berlin-1.0', 'deprecated': False},
@@ -641,6 +671,8 @@ LICENSES: dict[str, SPDXLicense] = {
     'unicode-tou': {'id': 'Unicode-TOU', 'deprecated': False},
     'unixcrypt': {'id': 'UnixCrypt', 'deprecated': False},
     'unlicense': {'id': 'Unlicense', 'deprecated': False},
+    'unlicense-libtelnet': {'id': 'Unlicense-libtelnet', 'deprecated': False},
+    'unlicense-libwhirlpool': {'id': 'Unlicense-libwhirlpool', 'deprecated': False},
     'upl-1.0': {'id': 'UPL-1.0', 'deprecated': False},
     'urt-rle': {'id': 'URT-RLE', 'deprecated': False},
     'vim': {'id': 'Vim', 'deprecated': False},
@@ -654,6 +686,7 @@ LICENSES: dict[str, SPDXLicense] = {
     'widget-workshop': {'id': 'Widget-Workshop', 'deprecated': False},
     'wsuipa': {'id': 'Wsuipa', 'deprecated': False},
     'wtfpl': {'id': 'WTFPL', 'deprecated': False},
+    'wwl': {'id': 'wwl', 'deprecated': False},
     'wxwindows': {'id': 'wxWindows', 'deprecated': True},
     'x11': {'id': 'X11', 'deprecated': False},
     'x11-distribute-modifications-variant': {'id': 'X11-distribute-modifications-variant', 'deprecated': False},
@@ -695,9 +728,11 @@ EXCEPTIONS: dict[str, SPDXException] = {
     'bison-exception-1.24': {'id': 'Bison-exception-1.24', 'deprecated': False},
     'bison-exception-2.2': {'id': 'Bison-exception-2.2', 'deprecated': False},
     'bootloader-exception': {'id': 'Bootloader-exception', 'deprecated': False},
+    'cgal-linking-exception': {'id': 'CGAL-linking-exception', 'deprecated': False},
     'classpath-exception-2.0': {'id': 'Classpath-exception-2.0', 'deprecated': False},
     'clisp-exception-2.0': {'id': 'CLISP-exception-2.0', 'deprecated': False},
     'cryptsetup-openssl-exception': {'id': 'cryptsetup-OpenSSL-exception', 'deprecated': False},
+    'digia-qt-lgpl-exception-1.1': {'id': 'Digia-Qt-LGPL-exception-1.1', 'deprecated': False},
     'digirule-foss-exception': {'id': 'DigiRule-FOSS-exception', 'deprecated': False},
     'ecos-exception-2.0': {'id': 'eCos-exception-2.0', 'deprecated': False},
     'erlang-otp-linking-exception': {'id': 'erlang-otp-linking-exception', 'deprecated': False},
@@ -714,13 +749,16 @@ EXCEPTIONS: dict[str, SPDXException] = {
     'gnome-examples-exception': {'id': 'GNOME-examples-exception', 'deprecated': False},
     'gnu-compiler-exception': {'id': 'GNU-compiler-exception', 'deprecated': False},
     'gnu-javamail-exception': {'id': 'gnu-javamail-exception', 'deprecated': False},
+    'gpl-3.0-389-ds-base-exception': {'id': 'GPL-3.0-389-ds-base-exception', 'deprecated': False},
     'gpl-3.0-interface-exception': {'id': 'GPL-3.0-interface-exception', 'deprecated': False},
     'gpl-3.0-linking-exception': {'id': 'GPL-3.0-linking-exception', 'deprecated': False},
     'gpl-3.0-linking-source-exception': {'id': 'GPL-3.0-linking-source-exception', 'deprecated': False},
     'gpl-cc-1.0': {'id': 'GPL-CC-1.0', 'deprecated': False},
     'gstreamer-exception-2005': {'id': 'GStreamer-exception-2005', 'deprecated': False},
     'gstreamer-exception-2008': {'id': 'GStreamer-exception-2008', 'deprecated': False},
+    'harbour-exception': {'id': 'harbour-exception', 'deprecated': False},
     'i2p-gpl-java-exception': {'id': 'i2p-gpl-java-exception', 'deprecated': False},
+    'independent-modules-exception': {'id': 'Independent-modules-exception', 'deprecated': False},
     'kicad-libraries-exception': {'id': 'KiCad-libraries-exception', 'deprecated': False},
     'lgpl-3.0-linking-exception': {'id': 'LGPL-3.0-linking-exception', 'deprecated': False},
     'libpri-openh323-exception': {'id': 'libpri-OpenH323-exception', 'deprecated': False},
@@ -730,12 +768,14 @@ EXCEPTIONS: dict[str, SPDXException] = {
     'llvm-exception': {'id': 'LLVM-exception', 'deprecated': False},
     'lzma-exception': {'id': 'LZMA-exception', 'deprecated': False},
     'mif-exception': {'id': 'mif-exception', 'deprecated': False},
+    'mxml-exception': {'id': 'mxml-exception', 'deprecated': False},
     'nokia-qt-exception-1.1': {'id': 'Nokia-Qt-exception-1.1', 'deprecated': True},
     'ocaml-lgpl-linking-exception': {'id': 'OCaml-LGPL-linking-exception', 'deprecated': False},
     'occt-exception-1.0': {'id': 'OCCT-exception-1.0', 'deprecated': False},
     'openjdk-assembly-exception-1.0': {'id': 'OpenJDK-assembly-exception-1.0', 'deprecated': False},
     'openvpn-openssl-exception': {'id': 'openvpn-openssl-exception', 'deprecated': False},
     'pcre2-exception': {'id': 'PCRE2-exception', 'deprecated': False},
+    'polyparse-exception': {'id': 'polyparse-exception', 'deprecated': False},
     'ps-or-pdf-font-exception-20170817': {'id': 'PS-or-PDF-font-exception-20170817', 'deprecated': False},
     'qpl-1.0-inria-2004-exception': {'id': 'QPL-1.0-INRIA-2004-exception', 'deprecated': False},
     'qt-gpl-exception-1.0': {'id': 'Qt-GPL-exception-1.0', 'deprecated': False},
diff --git a/contrib/python/packaging/py3/packaging/markers.py b/contrib/python/packaging/py3/packaging/markers.py
index e7cea57297a..ca3706fe492 100644
--- a/contrib/python/packaging/py3/packaging/markers.py
+++ b/contrib/python/packaging/py3/packaging/markers.py
@@ -8,7 +8,7 @@ import operator
 import os
 import platform
 import sys
-from typing import AbstractSet, Any, Callable, Literal, TypedDict, Union, cast
+from typing import AbstractSet, Callable, Literal, Mapping, TypedDict, Union, cast
 
 from ._parser import MarkerAtom, MarkerList, Op, Value, Variable
 from ._parser import parse_marker as _parse_marker
@@ -17,6 +17,7 @@ from .specifiers import InvalidSpecifier, Specifier
 from .utils import canonicalize_name
 
 __all__ = [
+    "Environment",
     "EvaluateContext",
     "InvalidMarker",
     "Marker",
@@ -28,6 +29,12 @@ __all__ = [
 Operator = Callable[[str, Union[str, AbstractSet[str]]], bool]
 EvaluateContext = Literal["metadata", "lock_file", "requirement"]
 MARKERS_ALLOWING_SET = {"extras", "dependency_groups"}
+MARKERS_REQUIRING_VERSION = {
+    "implementation_version",
+    "platform_release",
+    "python_full_version",
+    "python_version",
+}
 
 
 class InvalidMarker(ValueError):
@@ -121,20 +128,28 @@ class Environment(TypedDict):
     """
 
 
-def _normalize_extra_values(results: Any) -> Any:
+def _normalize_extras(
+    result: MarkerList | MarkerAtom | str,
+) -> MarkerList | MarkerAtom | str:
+    if not isinstance(result, tuple):
+        return result
+
+    lhs, op, rhs = result
+    if isinstance(lhs, Variable) and lhs.value == "extra":
+        normalized_extra = canonicalize_name(rhs.value)
+        rhs = Value(normalized_extra)
+    elif isinstance(rhs, Variable) and rhs.value == "extra":
+        normalized_extra = canonicalize_name(lhs.value)
+        lhs = Value(normalized_extra)
+    return lhs, op, rhs
+
+
+def _normalize_extra_values(results: MarkerList) -> MarkerList:
     """
     Normalize extra values.
     """
-    if isinstance(results[0], tuple):
-        lhs, op, rhs = results[0]
-        if isinstance(lhs, Variable) and lhs.value == "extra":
-            normalized_extra = canonicalize_name(rhs.value)
-            rhs = Value(normalized_extra)
-        elif isinstance(rhs, Variable) and rhs.value == "extra":
-            normalized_extra = canonicalize_name(lhs.value)
-            lhs = Value(normalized_extra)
-        results[0] = lhs, op, rhs
-    return results
+
+    return [_normalize_extras(r) for r in results]
 
 
 def _format_marker(
@@ -168,25 +183,26 @@ def _format_marker(
 _operators: dict[str, Operator] = {
     "in": lambda lhs, rhs: lhs in rhs,
     "not in": lambda lhs, rhs: lhs not in rhs,
-    "<": operator.lt,
-    "<=": operator.le,
+    "<": lambda _lhs, _rhs: False,
+    "<=": operator.eq,
     "==": operator.eq,
     "!=": operator.ne,
-    ">=": operator.ge,
-    ">": operator.gt,
+    ">=": operator.eq,
+    ">": lambda _lhs, _rhs: False,
 }
 
 
-def _eval_op(lhs: str, op: Op, rhs: str | AbstractSet[str]) -> bool:
-    if isinstance(rhs, str):
+def _eval_op(lhs: str, op: Op, rhs: str | AbstractSet[str], *, key: str) -> bool:
+    op_str = op.serialize()
+    if key in MARKERS_REQUIRING_VERSION:
         try:
-            spec = Specifier("".join([op.serialize(), rhs]))
+            spec = Specifier(f"{op_str}{rhs}")
         except InvalidSpecifier:
             pass
         else:
             return spec.contains(lhs, prereleases=True)
 
-    oper: Operator | None = _operators.get(op.serialize())
+    oper: Operator | None = _operators.get(op_str)
     if oper is None:
         raise UndefinedComparison(f"Undefined {op!r} on {lhs!r} and {rhs!r}.")
 
@@ -196,13 +212,14 @@ def _eval_op(lhs: str, op: Op, rhs: str | AbstractSet[str]) -> bool:
 def _normalize(
     lhs: str, rhs: str | AbstractSet[str], key: str
 ) -> tuple[str, str | AbstractSet[str]]:
-    # PEP 685 – Comparison of extra names for optional distribution dependencies
+    # PEP 685 - Comparison of extra names for optional distribution dependencies
     # https://peps.python.org/pep-0685/
     # > When comparing extra names, tools MUST normalize the names being
     # > compared using the semantics outlined in PEP 503 for names
     if key == "extra":
         assert isinstance(rhs, str), "extra value must be a string"
-        return (canonicalize_name(lhs), canonicalize_name(rhs))
+        # Both sides are normalized at this point already
+        return (lhs, rhs)
     if key in MARKERS_ALLOWING_SET:
         if isinstance(rhs, str):  # pragma: no cover
             return (canonicalize_name(lhs), canonicalize_name(rhs))
@@ -219,8 +236,6 @@ def _evaluate_markers(
     groups: list[list[bool]] = [[]]
 
     for marker in markers:
-        assert isinstance(marker, (list, tuple, str))
-
         if isinstance(marker, list):
             groups[-1].append(_evaluate_markers(marker, environment))
         elif isinstance(marker, tuple):
@@ -234,13 +249,16 @@ def _evaluate_markers(
                 lhs_value = lhs.value
                 environment_key = rhs.value
                 rhs_value = environment[environment_key]
+
             assert isinstance(lhs_value, str), "lhs must be a string"
             lhs_value, rhs_value = _normalize(lhs_value, rhs_value, key=environment_key)
-            groups[-1].append(_eval_op(lhs_value, op, rhs_value))
-        else:
-            assert marker in ["and", "or"]
-            if marker == "or":
-                groups.append([])
+            groups[-1].append(_eval_op(lhs_value, op, rhs_value, key=environment_key))
+        elif marker == "or":
+            groups.append([])
+        elif marker == "and":
+            pass
+        else:  # pragma: nocover
+            raise TypeError(f"Unexpected marker {marker!r}")
 
     return any(all(item) for item in groups)
 
@@ -276,6 +294,11 @@ class Marker:
         # Note: We create a Marker object without calling this constructor in
         #       packaging.requirements.Requirement. If any additional logic is
         #       added here, make sure to mirror/adapt Requirement.
+
+        # If this fails and throws an error, the repr still expects _markers to
+        # be defined.
+        self._markers: MarkerList = []
+
         try:
             self._markers = _normalize_extra_values(_parse_marker(marker))
             # The attribute `_markers` can be described in terms of a recursive type:
@@ -301,12 +324,12 @@ class Marker:
         return _format_marker(self._markers)
 
     def __repr__(self) -> str:
-        return f"<Marker('{self}')>"
+        return f"<{self.__class__.__name__}('{self}')>"
 
     def __hash__(self) -> int:
-        return hash((self.__class__.__name__, str(self)))
+        return hash(str(self))
 
-    def __eq__(self, other: Any) -> bool:
+    def __eq__(self, other: object) -> bool:
         if not isinstance(other, Marker):
             return NotImplemented
 
@@ -314,7 +337,7 @@ class Marker:
 
     def evaluate(
         self,
-        environment: dict[str, str] | None = None,
+        environment: Mapping[str, str | AbstractSet[str]] | None = None,
         context: EvaluateContext = "metadata",
     ) -> bool:
         """Evaluate a marker.
@@ -337,12 +360,15 @@ class Marker:
             )
         elif context == "metadata":
             current_environment["extra"] = ""
+
         if environment is not None:
             current_environment.update(environment)
-            # The API used to allow setting extra to None. We need to handle this
-            # case for backwards compatibility.
-            if "extra" in current_environment and current_environment["extra"] is None:
-                current_environment["extra"] = ""
+            if "extra" in current_environment:
+                # The API used to allow setting extra to None. We need to handle
+                # this case for backwards compatibility. Also skip running
+                # normalize name if extra is empty.
+                extra = cast("str | None", current_environment["extra"])
+                current_environment["extra"] = canonicalize_name(extra) if extra else ""
 
         return _evaluate_markers(
             self._markers, _repair_python_full_version(current_environment)
@@ -356,7 +382,7 @@ def _repair_python_full_version(
     Work around platform.python_version() returning something that is not PEP 440
     compliant for non-tagged Python builds.
     """
-    python_full_version = cast(str, env["python_full_version"])
+    python_full_version = cast("str", env["python_full_version"])
     if python_full_version.endswith("+"):
         env["python_full_version"] = f"{python_full_version}local"
     return env
diff --git a/contrib/python/packaging/py3/packaging/metadata.py b/contrib/python/packaging/py3/packaging/metadata.py
index 3bd8602d36c..253f6b1b7eb 100644
--- a/contrib/python/packaging/py3/packaging/metadata.py
+++ b/contrib/python/packaging/py3/packaging/metadata.py
@@ -5,6 +5,7 @@ import email.header
 import email.message
 import email.parser
 import email.policy
+import keyword
 import pathlib
 import sys
 import typing
@@ -19,13 +20,15 @@ from typing import (
 
 from . import licenses, requirements, specifiers, utils
 from . import version as version_module
-from .licenses import NormalizedLicenseExpression
+
+if typing.TYPE_CHECKING:
+    from .licenses import NormalizedLicenseExpression
 
 T = typing.TypeVar("T")
 
 
 if sys.version_info >= (3, 11):  # pragma: no cover
-    ExceptionGroup = ExceptionGroup
+    ExceptionGroup = ExceptionGroup  # noqa: F821
 else:  # pragma: no cover
 
     class ExceptionGroup(Exception):
@@ -126,13 +129,19 @@ class RawMetadata(TypedDict, total=False):
 
     # Metadata 2.3 - PEP 685
     # No new fields were added in PEP 685, just some edge case were
-    # tightened up to provide better interoptability.
+    # tightened up to provide better interoperability.
 
     # Metadata 2.4 - PEP 639
     license_expression: str
     license_files: list[str]
 
+    # Metadata 2.5 - PEP 794
+    import_names: list[str]
+    import_namespaces: list[str]
+
 
+# 'keywords' is special as it's a string in the core metadata spec, but we
+# represent it as a list.
 _STRING_FIELDS = {
     "author",
     "author_email",
@@ -165,6 +174,8 @@ _LIST_FIELDS = {
     "requires_dist",
     "requires_external",
     "supported_platforms",
+    "import_names",
+    "import_namespaces",
 }
 
 _DICT_FIELDS = {
@@ -193,24 +204,23 @@ def _parse_project_urls(data: list[str]) -> dict[str, str]:
         # be the missing value, then they'd have multiple '' values that
         # overwrite each other in a accumulating dict.
         #
-        # The other potentional issue is that it's possible to have the
+        # The other potential issue is that it's possible to have the
         # same label multiple times in the metadata, with no solid "right"
         # answer with what to do in that case. As such, we'll do the only
-        # thing we can, which is treat the field as unparseable and add it
+        # thing we can, which is treat the field as unparsable and add it
         # to our list of unparsed fields.
-        parts = [p.strip() for p in pair.split(",", 1)]
-        parts.extend([""] * (max(0, 2 - len(parts))))  # Ensure 2 items
-
+        #
         # TODO: The spec doesn't say anything about if the keys should be
         #       considered case sensitive or not... logically they should
         #       be case-preserving and case-insensitive, but doing that
         #       would open up more cases where we might have duplicate
         #       entries.
-        label, url = parts
+        label, _, url = (s.strip() for s in pair.partition(","))
+
         if label in urls:
             # The label already exists in our set of urls, so this field
-            # is unparseable, and we can just add the whole thing to our
-            # unparseable data and stop processing it.
+            # is unparsable, and we can just add the whole thing to our
+            # unparsable data and stop processing it.
             raise KeyError("duplicate labels in project urls")
         urls[label] = url
 
@@ -257,6 +267,8 @@ _EMAIL_TO_RAW_MAPPING = {
     "download-url": "download_url",
     "dynamic": "dynamic",
     "home-page": "home_page",
+    "import-name": "import_names",
+    "import-namespace": "import_namespaces",
     "keywords": "keywords",
     "license": "license",
     "license-expression": "license_expression",
@@ -283,6 +295,45 @@ _EMAIL_TO_RAW_MAPPING = {
 _RAW_TO_EMAIL_MAPPING = {raw: email for email, raw in _EMAIL_TO_RAW_MAPPING.items()}
 
 
+# This class is for writing RFC822 messages
+class RFC822Policy(email.policy.EmailPolicy):
+    """
+    This is :class:`email.policy.EmailPolicy`, but with a simple ``header_store_parse``
+    implementation that handles multi-line values, and some nice defaults.
+    """
+
+    utf8 = True
+    mangle_from_ = False
+    max_line_length = 0
+
+    def header_store_parse(self, name: str, value: str) -> tuple[str, str]:
+        size = len(name) + 2
+        value = value.replace("\n", "\n" + " " * size)
+        return (name, value)
+
+
+# This class is for writing RFC822 messages
+class RFC822Message(email.message.EmailMessage):
+    """
+    This is :class:`email.message.EmailMessage` with two small changes: it defaults to
+    our `RFC822Policy`, and it correctly writes unicode when being called
+    with `bytes()`.
+    """
+
+    def __init__(self) -> None:
+        super().__init__(policy=RFC822Policy())
+
+    def as_bytes(
+        self, unixfrom: bool = False, policy: email.policy.Policy | None = None
+    ) -> bytes:
+        """
+        Return the bytes representation of the message.
+
+        This handles unicode encoding.
+        """
+        return self.as_string(unixfrom, policy=policy).encode("utf-8")
+
+
 def parse_email(data: bytes | str) -> tuple[RawMetadata, dict[str, list[str]]]:
     """Parse a distribution's metadata stored as email headers (e.g. from ``METADATA``).
 
@@ -310,10 +361,10 @@ def parse_email(data: bytes | str) -> tuple[RawMetadata, dict[str, list[str]]]:
     # We have to wrap parsed.keys() in a set, because in the case of multiple
     # values for a key (a list), the key will appear multiple times in the
     # list of keys, but we're avoiding that by using get_all().
-    for name in frozenset(parsed.keys()):
+    for name_with_case in frozenset(parsed.keys()):
         # Header names in RFC are case insensitive, so we'll normalize to all
         # lower case to make comparisons easier.
-        name = name.lower()
+        name = name_with_case.lower()
 
         # We use get_all() here, even for fields that aren't multiple use,
         # because otherwise someone could have e.g. two Name fields, and we
@@ -349,16 +400,16 @@ def parse_email(data: bytes | str) -> tuple[RawMetadata, dict[str, list[str]]]:
                 # can be independently encoded, so we'll need to check each
                 # of them.
                 chunks: list[tuple[bytes, str | None]] = []
-                for bin, encoding in email.header.decode_header(h):
+                for binary, _encoding in email.header.decode_header(h):
                     try:
-                        bin.decode("utf8", "strict")
+                        binary.decode("utf8", "strict")
                     except UnicodeDecodeError:
                         # Enable mojibake.
                         encoding = "latin1"
                         valid_encoding = False
                     else:
                         encoding = "utf8"
-                    chunks.append((bin, encoding))
+                    chunks.append((binary, encoding))
 
                 # Turn our chunks back into a Header object, then let that
                 # Header object do the right thing to turn them into a
@@ -397,6 +448,11 @@ def parse_email(data: bytes | str) -> tuple[RawMetadata, dict[str, list[str]]]:
         # of unparsed stuff.
         if raw_name in _STRING_FIELDS and len(value) == 1:
             raw[raw_name] = value[0]
+        # If this is import_names, we need to special case the empty field
+        # case, which converts to an empty list instead of None. We can't let
+        # the empty case slip through, as it will fail validation.
+        elif raw_name == "import_names" and value == [""]:
+            raw[raw_name] = []
         # If this is one of our list of string fields, then we can just assign
         # the value, since email *only* has strings, and our get_all() call
         # above ensures that this is a list.
@@ -424,7 +480,7 @@ def parse_email(data: bytes | str) -> tuple[RawMetadata, dict[str, list[str]]]:
             except KeyError:
                 unparsed[name] = value
         # Nothing that we've done has managed to parse this, so it'll just
-        # throw it in our unparseable data and move on.
+        # throw it in our unparsable data and move on.
         else:
             unparsed[name] = value
 
@@ -441,9 +497,9 @@ def parse_email(data: bytes | str) -> tuple[RawMetadata, dict[str, list[str]]]:
     else:
         if payload:
             # Check to see if we've already got a description, if so then both
-            # it, and this body move to unparseable.
+            # it, and this body move to unparsable.
             if "description" in raw:
-                description_header = cast(str, raw.pop("description"))
+                description_header = cast("str", raw.pop("description"))
                 unparsed.setdefault("description", []).extend(
                     [description_header, payload]
                 )
@@ -456,15 +512,15 @@ def parse_email(data: bytes | str) -> tuple[RawMetadata, dict[str, list[str]]]:
     # literal key names, but we're computing our key names on purpose, but the
     # way this function is implemented, our `TypedDict` can only have valid key
     # names.
-    return cast(RawMetadata, raw), unparsed
+    return cast("RawMetadata", raw), unparsed
 
 
 _NOT_FOUND = object()
 
 
 # Keep the two values in sync.
-_VALID_METADATA_VERSIONS = ["1.0", "1.1", "1.2", "2.1", "2.2", "2.3", "2.4"]
-_MetadataVersion = Literal["1.0", "1.1", "1.2", "2.1", "2.2", "2.3", "2.4"]
+_VALID_METADATA_VERSIONS = ["1.0", "1.1", "1.2", "2.1", "2.2", "2.3", "2.4", "2.5"]
+_MetadataVersion = Literal["1.0", "1.1", "1.2", "2.1", "2.2", "2.3", "2.4", "2.5"]
 
 _REQUIRED_ATTRS = frozenset(["metadata_version", "name", "version"])
 
@@ -519,7 +575,7 @@ class _Validator(Generic[T]):
         except KeyError:
             pass
 
-        return cast(T, value)
+        return cast("T", value)
 
     def _invalid_metadata(
         self, msg: str, cause: Exception | None = None
@@ -534,7 +590,7 @@ class _Validator(Generic[T]):
         # Implicitly makes Metadata-Version required.
         if value not in _VALID_METADATA_VERSIONS:
             raise self._invalid_metadata(f"{value!r} is not a valid metadata version")
-        return cast(_MetadataVersion, value)
+        return cast("_MetadataVersion", value)
 
     def _process_name(self, value: str) -> str:
         if not value:
@@ -647,9 +703,7 @@ class _Validator(Generic[T]):
         else:
             return reqs
 
-    def _process_license_expression(
-        self, value: str
-    ) -> NormalizedLicenseExpression | None:
+    def _process_license_expression(self, value: str) -> NormalizedLicenseExpression:
         try:
             return licenses.canonicalize_license_expression(value)
         except ValueError as exc:
@@ -683,6 +737,30 @@ class _Validator(Generic[T]):
             paths.append(path)
         return paths
 
+    def _process_import_names(self, value: list[str]) -> list[str]:
+        for import_name in value:
+            name, semicolon, private = import_name.partition(";")
+            name = name.rstrip()
+            for identifier in name.split("."):
+                if not identifier.isidentifier():
+                    raise self._invalid_metadata(
+                        f"{name!r} is invalid for {{field}}; "
+                        f"{identifier!r} is not a valid identifier"
+                    )
+                elif keyword.iskeyword(identifier):
+                    raise self._invalid_metadata(
+                        f"{name!r} is invalid for {{field}}; "
+                        f"{identifier!r} is a keyword"
+                    )
+            if semicolon and private.lstrip() != "private":
+                raise self._invalid_metadata(
+                    f"{import_name!r} is invalid for {{field}}; "
+                    "the only valid option is 'private'"
+                )
+        return value
+
+    _process_import_namespaces = _process_import_names
+
 
 class Metadata:
     """Representation of distribution metadata.
@@ -854,9 +932,47 @@ class Metadata:
     """:external:ref:`core-metadata-provides-dist`"""
     obsoletes_dist: _Validator[list[str] | None] = _Validator(added="1.2")
     """:external:ref:`core-metadata-obsoletes-dist`"""
+    import_names: _Validator[list[str] | None] = _Validator(added="2.5")
+    """:external:ref:`core-metadata-import-name`"""
+    import_namespaces: _Validator[list[str] | None] = _Validator(added="2.5")
+    """:external:ref:`core-metadata-import-namespace`"""
     requires: _Validator[list[str] | None] = _Validator(added="1.1")
     """``Requires`` (deprecated)"""
     provides: _Validator[list[str] | None] = _Validator(added="1.1")
     """``Provides`` (deprecated)"""
     obsoletes: _Validator[list[str] | None] = _Validator(added="1.1")
     """``Obsoletes`` (deprecated)"""
+
+    def as_rfc822(self) -> RFC822Message:
+        """
+        Return an RFC822 message with the metadata.
+        """
+        message = RFC822Message()
+        self._write_metadata(message)
+        return message
+
+    def _write_metadata(self, message: RFC822Message) -> None:
+        """
+        Return an RFC822 message with the metadata.
+        """
+        for name, validator in self.__class__.__dict__.items():
+            if isinstance(validator, _Validator) and name != "description":
+                value = getattr(self, name)
+                email_name = _RAW_TO_EMAIL_MAPPING[name]
+                if value is not None:
+                    if email_name == "project-url":
+                        for label, url in value.items():
+                            message[email_name] = f"{label}, {url}"
+                    elif email_name == "keywords":
+                        message[email_name] = ",".join(value)
+                    elif email_name == "import-name" and value == []:
+                        message[email_name] = ""
+                    elif isinstance(value, list):
+                        for item in value:
+                            message[email_name] = str(item)
+                    else:
+                        message[email_name] = str(value)
+
+        # The description is a special case because it is in the body of the message.
+        if self.description is not None:
+            message.set_payload(self.description)
diff --git a/contrib/python/packaging/py3/packaging/pylock.py b/contrib/python/packaging/py3/packaging/pylock.py
new file mode 100644
index 00000000000..a564f15246a
--- /dev/null
+++ b/contrib/python/packaging/py3/packaging/pylock.py
@@ -0,0 +1,635 @@
+from __future__ import annotations
+
+import dataclasses
+import logging
+import re
+from collections.abc import Mapping, Sequence
+from dataclasses import dataclass
+from datetime import datetime
+from typing import (
+    TYPE_CHECKING,
+    Any,
+    Callable,
+    Protocol,
+    TypeVar,
+)
+
+from .markers import Marker
+from .specifiers import SpecifierSet
+from .utils import NormalizedName, is_normalized_name
+from .version import Version
+
+if TYPE_CHECKING:  # pragma: no cover
+    from pathlib import Path
+
+    from typing_extensions import Self
+
+_logger = logging.getLogger(__name__)
+
+__all__ = [
+    "Package",
+    "PackageArchive",
+    "PackageDirectory",
+    "PackageSdist",
+    "PackageVcs",
+    "PackageWheel",
+    "Pylock",
+    "PylockUnsupportedVersionError",
+    "PylockValidationError",
+    "is_valid_pylock_path",
+]
+
+_T = TypeVar("_T")
+_T2 = TypeVar("_T2")
+
+
+class _FromMappingProtocol(Protocol):  # pragma: no cover
+    @classmethod
+    def _from_dict(cls, d: Mapping[str, Any]) -> Self: ...
+
+
+_FromMappingProtocolT = TypeVar("_FromMappingProtocolT", bound=_FromMappingProtocol)
+
+
+_PYLOCK_FILE_NAME_RE = re.compile(r"^pylock\.([^.]+)\.toml$")
+
+
+def is_valid_pylock_path(path: Path) -> bool:
+    """Check if the given path is a valid pylock file path."""
+    return path.name == "pylock.toml" or bool(_PYLOCK_FILE_NAME_RE.match(path.name))
+
+
+def _toml_key(key: str) -> str:
+    return key.replace("_", "-")
+
+
+def _toml_value(key: str, value: Any) -> Any:  # noqa: ANN401
+    if isinstance(value, (Version, Marker, SpecifierSet)):
+        return str(value)
+    if isinstance(value, Sequence) and key == "environments":
+        return [str(v) for v in value]
+    return value
+
+
+def _toml_dict_factory(data: list[tuple[str, Any]]) -> dict[str, Any]:
+    return {
+        _toml_key(key): _toml_value(key, value)
+        for key, value in data
+        if value is not None
+    }
+
+
+def _get(d: Mapping[str, Any], expected_type: type[_T], key: str) -> _T | None:
+    """Get a value from the dictionary and verify it's the expected type."""
+    if (value := d.get(key)) is None:
+        return None
+    if not isinstance(value, expected_type):
+        raise PylockValidationError(
+            f"Unexpected type {type(value).__name__} "
+            f"(expected {expected_type.__name__})",
+            context=key,
+        )
+    return value
+
+
+def _get_required(d: Mapping[str, Any], expected_type: type[_T], key: str) -> _T:
+    """Get a required value from the dictionary and verify it's the expected type."""
+    if (value := _get(d, expected_type, key)) is None:
+        raise _PylockRequiredKeyError(key)
+    return value
+
+
+def _get_sequence(
+    d: Mapping[str, Any], expected_item_type: type[_T], key: str
+) -> Sequence[_T] | None:
+    """Get a list value from the dictionary and verify it's the expected items type."""
+    if (value := _get(d, Sequence, key)) is None:  # type: ignore[type-abstract]
+        return None
+    if isinstance(value, (str, bytes)):
+        # special case: str and bytes are Sequences, but we want to reject it
+        raise PylockValidationError(
+            f"Unexpected type {type(value).__name__} (expected Sequence)",
+            context=key,
+        )
+    for i, item in enumerate(value):
+        if not isinstance(item, expected_item_type):
+            raise PylockValidationError(
+                f"Unexpected type {type(item).__name__} "
+                f"(expected {expected_item_type.__name__})",
+                context=f"{key}[{i}]",
+            )
+    return value
+
+
+def _get_as(
+    d: Mapping[str, Any],
+    expected_type: type[_T],
+    target_type: Callable[[_T], _T2],
+    key: str,
+) -> _T2 | None:
+    """Get a value from the dictionary, verify it's the expected type,
+    and convert to the target type.
+
+    This assumes the target_type constructor accepts the value.
+    """
+    if (value := _get(d, expected_type, key)) is None:
+        return None
+    try:
+        return target_type(value)
+    except Exception as e:
+        raise PylockValidationError(e, context=key) from e
+
+
+def _get_required_as(
+    d: Mapping[str, Any],
+    expected_type: type[_T],
+    target_type: Callable[[_T], _T2],
+    key: str,
+) -> _T2:
+    """Get a required value from the dict, verify it's the expected type,
+    and convert to the target type."""
+    if (value := _get_as(d, expected_type, target_type, key)) is None:
+        raise _PylockRequiredKeyError(key)
+    return value
+
+
+def _get_sequence_as(
+    d: Mapping[str, Any],
+    expected_item_type: type[_T],
+    target_item_type: Callable[[_T], _T2],
+    key: str,
+) -> list[_T2] | None:
+    """Get list value from dictionary and verify expected items type."""
+    if (value := _get_sequence(d, expected_item_type, key)) is None:
+        return None
+    result = []
+    try:
+        for item in value:
+            typed_item = target_item_type(item)
+            result.append(typed_item)
+    except Exception as e:
+        raise PylockValidationError(e, context=f"{key}[{len(result)}]") from e
+    return result
+
+
+def _get_object(
+    d: Mapping[str, Any], target_type: type[_FromMappingProtocolT], key: str
+) -> _FromMappingProtocolT | None:
+    """Get a dictionary value from the dictionary and convert it to a dataclass."""
+    if (value := _get(d, Mapping, key)) is None:  # type: ignore[type-abstract]
+        return None
+    try:
+        return target_type._from_dict(value)
+    except Exception as e:
+        raise PylockValidationError(e, context=key) from e
+
+
+def _get_sequence_of_objects(
+    d: Mapping[str, Any], target_item_type: type[_FromMappingProtocolT], key: str
+) -> list[_FromMappingProtocolT] | None:
+    """Get a list value from the dictionary and convert its items to a dataclass."""
+    if (value := _get_sequence(d, Mapping, key)) is None:  # type: ignore[type-abstract]
+        return None
+    result: list[_FromMappingProtocolT] = []
+    try:
+        for item in value:
+            typed_item = target_item_type._from_dict(item)
+            result.append(typed_item)
+    except Exception as e:
+        raise PylockValidationError(e, context=f"{key}[{len(result)}]") from e
+    return result
+
+
+def _get_required_sequence_of_objects(
+    d: Mapping[str, Any], target_item_type: type[_FromMappingProtocolT], key: str
+) -> Sequence[_FromMappingProtocolT]:
+    """Get a required list value from the dictionary and convert its items to a
+    dataclass."""
+    if (result := _get_sequence_of_objects(d, target_item_type, key)) is None:
+        raise _PylockRequiredKeyError(key)
+    return result
+
+
+def _validate_normalized_name(name: str) -> NormalizedName:
+    """Validate that a string is a NormalizedName."""
+    if not is_normalized_name(name):
+        raise PylockValidationError(f"Name {name!r} is not normalized")
+    return NormalizedName(name)
+
+
+def _validate_path_url(path: str | None, url: str | None) -> None:
+    if not path and not url:
+        raise PylockValidationError("path or url must be provided")
+
+
+def _validate_hashes(hashes: Mapping[str, Any]) -> Mapping[str, Any]:
+    if not hashes:
+        raise PylockValidationError("At least one hash must be provided")
+    if not all(isinstance(hash_val, str) for hash_val in hashes.values()):
+        raise PylockValidationError("Hash values must be strings")
+    return hashes
+
+
+class PylockValidationError(Exception):
+    """Raised when when input data is not spec-compliant."""
+
+    context: str | None = None
+    message: str
+
+    def __init__(
+        self,
+        cause: str | Exception,
+        *,
+        context: str | None = None,
+    ) -> None:
+        if isinstance(cause, PylockValidationError):
+            if cause.context:
+                self.context = (
+                    f"{context}.{cause.context}" if context else cause.context
+                )
+            else:
+                self.context = context
+            self.message = cause.message
+        else:
+            self.context = context
+            self.message = str(cause)
+
+    def __str__(self) -> str:
+        if self.context:
+            return f"{self.message} in {self.context!r}"
+        return self.message
+
+
+class _PylockRequiredKeyError(PylockValidationError):
+    def __init__(self, key: str) -> None:
+        super().__init__("Missing required value", context=key)
+
+
+class PylockUnsupportedVersionError(PylockValidationError):
+    """Raised when encountering an unsupported `lock_version`."""
+
+
+@dataclass(frozen=True, init=False)
+class PackageVcs:
+    type: str
+    url: str | None = None
+    path: str | None = None
+    requested_revision: str | None = None
+    commit_id: str  # type: ignore[misc]
+    subdirectory: str | None = None
+
+    def __init__(
+        self,
+        *,
+        type: str,
+        url: str | None = None,
+        path: str | None = None,
+        requested_revision: str | None = None,
+        commit_id: str,
+        subdirectory: str | None = None,
+    ) -> None:
+        # In Python 3.10+ make dataclass kw_only=True and remove __init__
+        object.__setattr__(self, "type", type)
+        object.__setattr__(self, "url", url)
+        object.__setattr__(self, "path", path)
+        object.__setattr__(self, "requested_revision", requested_revision)
+        object.__setattr__(self, "commit_id", commit_id)
+        object.__setattr__(self, "subdirectory", subdirectory)
+
+    @classmethod
+    def _from_dict(cls, d: Mapping[str, Any]) -> Self:
+        package_vcs = cls(
+            type=_get_required(d, str, "type"),
+            url=_get(d, str, "url"),
+            path=_get(d, str, "path"),
+            requested_revision=_get(d, str, "requested-revision"),
+            commit_id=_get_required(d, str, "commit-id"),
+            subdirectory=_get(d, str, "subdirectory"),
+        )
+        _validate_path_url(package_vcs.path, package_vcs.url)
+        return package_vcs
+
+
+@dataclass(frozen=True, init=False)
+class PackageDirectory:
+    path: str
+    editable: bool | None = None
+    subdirectory: str | None = None
+
+    def __init__(
+        self,
+        *,
+        path: str,
+        editable: bool | None = None,
+        subdirectory: str | None = None,
+    ) -> None:
+        # In Python 3.10+ make dataclass kw_only=True and remove __init__
+        object.__setattr__(self, "path", path)
+        object.__setattr__(self, "editable", editable)
+        object.__setattr__(self, "subdirectory", subdirectory)
+
+    @classmethod
+    def _from_dict(cls, d: Mapping[str, Any]) -> Self:
+        return cls(
+            path=_get_required(d, str, "path"),
+            editable=_get(d, bool, "editable"),
+            subdirectory=_get(d, str, "subdirectory"),
+        )
+
+
+@dataclass(frozen=True, init=False)
+class PackageArchive:
+    url: str | None = None
+    path: str | None = None
+    size: int | None = None
+    upload_time: datetime | None = None
+    hashes: Mapping[str, str]  # type: ignore[misc]
+    subdirectory: str | None = None
+
+    def __init__(
+        self,
+        *,
+        url: str | None = None,
+        path: str | None = None,
+        size: int | None = None,
+        upload_time: datetime | None = None,
+        hashes: Mapping[str, str],
+        subdirectory: str | None = None,
+    ) -> None:
+        # In Python 3.10+ make dataclass kw_only=True and remove __init__
+        object.__setattr__(self, "url", url)
+        object.__setattr__(self, "path", path)
+        object.__setattr__(self, "size", size)
+        object.__setattr__(self, "upload_time", upload_time)
+        object.__setattr__(self, "hashes", hashes)
+        object.__setattr__(self, "subdirectory", subdirectory)
+
+    @classmethod
+    def _from_dict(cls, d: Mapping[str, Any]) -> Self:
+        package_archive = cls(
+            url=_get(d, str, "url"),
+            path=_get(d, str, "path"),
+            size=_get(d, int, "size"),
+            upload_time=_get(d, datetime, "upload-time"),
+            hashes=_get_required_as(d, Mapping, _validate_hashes, "hashes"),  # type: ignore[type-abstract]
+            subdirectory=_get(d, str, "subdirectory"),
+        )
+        _validate_path_url(package_archive.path, package_archive.url)
+        return package_archive
+
+
+@dataclass(frozen=True, init=False)
+class PackageSdist:
+    name: str | None = None
+    upload_time: datetime | None = None
+    url: str | None = None
+    path: str | None = None
+    size: int | None = None
+    hashes: Mapping[str, str]  # type: ignore[misc]
+
+    def __init__(
+        self,
+        *,
+        name: str | None = None,
+        upload_time: datetime | None = None,
+        url: str | None = None,
+        path: str | None = None,
+        size: int | None = None,
+        hashes: Mapping[str, str],
+    ) -> None:
+        # In Python 3.10+ make dataclass kw_only=True and remove __init__
+        object.__setattr__(self, "name", name)
+        object.__setattr__(self, "upload_time", upload_time)
+        object.__setattr__(self, "url", url)
+        object.__setattr__(self, "path", path)
+        object.__setattr__(self, "size", size)
+        object.__setattr__(self, "hashes", hashes)
+
+    @classmethod
+    def _from_dict(cls, d: Mapping[str, Any]) -> Self:
+        package_sdist = cls(
+            name=_get(d, str, "name"),
+            upload_time=_get(d, datetime, "upload-time"),
+            url=_get(d, str, "url"),
+            path=_get(d, str, "path"),
+            size=_get(d, int, "size"),
+            hashes=_get_required_as(d, Mapping, _validate_hashes, "hashes"),  # type: ignore[type-abstract]
+        )
+        _validate_path_url(package_sdist.path, package_sdist.url)
+        return package_sdist
+
+
+@dataclass(frozen=True, init=False)
+class PackageWheel:
+    name: str | None = None
+    upload_time: datetime | None = None
+    url: str | None = None
+    path: str | None = None
+    size: int | None = None
+    hashes: Mapping[str, str]  # type: ignore[misc]
+
+    def __init__(
+        self,
+        *,
+        name: str | None = None,
+        upload_time: datetime | None = None,
+        url: str | None = None,
+        path: str | None = None,
+        size: int | None = None,
+        hashes: Mapping[str, str],
+    ) -> None:
+        # In Python 3.10+ make dataclass kw_only=True and remove __init__
+        object.__setattr__(self, "name", name)
+        object.__setattr__(self, "upload_time", upload_time)
+        object.__setattr__(self, "url", url)
+        object.__setattr__(self, "path", path)
+        object.__setattr__(self, "size", size)
+        object.__setattr__(self, "hashes", hashes)
+
+    @classmethod
+    def _from_dict(cls, d: Mapping[str, Any]) -> Self:
+        package_wheel = cls(
+            name=_get(d, str, "name"),
+            upload_time=_get(d, datetime, "upload-time"),
+            url=_get(d, str, "url"),
+            path=_get(d, str, "path"),
+            size=_get(d, int, "size"),
+            hashes=_get_required_as(d, Mapping, _validate_hashes, "hashes"),  # type: ignore[type-abstract]
+        )
+        _validate_path_url(package_wheel.path, package_wheel.url)
+        return package_wheel
+
+
+@dataclass(frozen=True, init=False)
+class Package:
+    name: NormalizedName
+    version: Version | None = None
+    marker: Marker | None = None
+    requires_python: SpecifierSet | None = None
+    dependencies: Sequence[Mapping[str, Any]] | None = None
+    vcs: PackageVcs | None = None
+    directory: PackageDirectory | None = None
+    archive: PackageArchive | None = None
+    index: str | None = None
+    sdist: PackageSdist | None = None
+    wheels: Sequence[PackageWheel] | None = None
+    attestation_identities: Sequence[Mapping[str, Any]] | None = None
+    tool: Mapping[str, Any] | None = None
+
+    def __init__(
+        self,
+        *,
+        name: NormalizedName,
+        version: Version | None = None,
+        marker: Marker | None = None,
+        requires_python: SpecifierSet | None = None,
+        dependencies: Sequence[Mapping[str, Any]] | None = None,
+        vcs: PackageVcs | None = None,
+        directory: PackageDirectory | None = None,
+        archive: PackageArchive | None = None,
+        index: str | None = None,
+        sdist: PackageSdist | None = None,
+        wheels: Sequence[PackageWheel] | None = None,
+        attestation_identities: Sequence[Mapping[str, Any]] | None = None,
+        tool: Mapping[str, Any] | None = None,
+    ) -> None:
+        # In Python 3.10+ make dataclass kw_only=True and remove __init__
+        object.__setattr__(self, "name", name)
+        object.__setattr__(self, "version", version)
+        object.__setattr__(self, "marker", marker)
+        object.__setattr__(self, "requires_python", requires_python)
+        object.__setattr__(self, "dependencies", dependencies)
+        object.__setattr__(self, "vcs", vcs)
+        object.__setattr__(self, "directory", directory)
+        object.__setattr__(self, "archive", archive)
+        object.__setattr__(self, "index", index)
+        object.__setattr__(self, "sdist", sdist)
+        object.__setattr__(self, "wheels", wheels)
+        object.__setattr__(self, "attestation_identities", attestation_identities)
+        object.__setattr__(self, "tool", tool)
+
+    @classmethod
+    def _from_dict(cls, d: Mapping[str, Any]) -> Self:
+        package = cls(
+            name=_get_required_as(d, str, _validate_normalized_name, "name"),
+            version=_get_as(d, str, Version, "version"),
+            requires_python=_get_as(d, str, SpecifierSet, "requires-python"),
+            dependencies=_get_sequence(d, Mapping, "dependencies"),  # type: ignore[type-abstract]
+            marker=_get_as(d, str, Marker, "marker"),
+            vcs=_get_object(d, PackageVcs, "vcs"),
+            directory=_get_object(d, PackageDirectory, "directory"),
+            archive=_get_object(d, PackageArchive, "archive"),
+            index=_get(d, str, "index"),
+            sdist=_get_object(d, PackageSdist, "sdist"),
+            wheels=_get_sequence_of_objects(d, PackageWheel, "wheels"),
+            attestation_identities=_get_sequence(d, Mapping, "attestation-identities"),  # type: ignore[type-abstract]
+            tool=_get(d, Mapping, "tool"),  # type: ignore[type-abstract]
+        )
+        distributions = bool(package.sdist) + len(package.wheels or [])
+        direct_urls = (
+            bool(package.vcs) + bool(package.directory) + bool(package.archive)
+        )
+        if distributions > 0 and direct_urls > 0:
+            raise PylockValidationError(
+                "None of vcs, directory, archive must be set if sdist or wheels are set"
+            )
+        if distributions == 0 and direct_urls != 1:
+            raise PylockValidationError(
+                "Exactly one of vcs, directory, archive must be set "
+                "if sdist and wheels are not set"
+            )
+        try:
+            for i, attestation_identity in enumerate(  # noqa: B007
+                package.attestation_identities or []
+            ):
+                _get_required(attestation_identity, str, "kind")
+        except Exception as e:
+            raise PylockValidationError(
+                e, context=f"attestation-identities[{i}]"
+            ) from e
+        return package
+
+    @property
+    def is_direct(self) -> bool:
+        return not (self.sdist or self.wheels)
+
+
+@dataclass(frozen=True, init=False)
+class Pylock:
+    """A class representing a pylock file."""
+
+    lock_version: Version
+    environments: Sequence[Marker] | None = None
+    requires_python: SpecifierSet | None = None
+    extras: Sequence[NormalizedName] | None = None
+    dependency_groups: Sequence[str] | None = None
+    default_groups: Sequence[str] | None = None
+    created_by: str  # type: ignore[misc]
+    packages: Sequence[Package]  # type: ignore[misc]
+    tool: Mapping[str, Any] | None = None
+
+    def __init__(
+        self,
+        *,
+        lock_version: Version,
+        environments: Sequence[Marker] | None = None,
+        requires_python: SpecifierSet | None = None,
+        extras: Sequence[NormalizedName] | None = None,
+        dependency_groups: Sequence[str] | None = None,
+        default_groups: Sequence[str] | None = None,
+        created_by: str,
+        packages: Sequence[Package],
+        tool: Mapping[str, Any] | None = None,
+    ) -> None:
+        # In Python 3.10+ make dataclass kw_only=True and remove __init__
+        object.__setattr__(self, "lock_version", lock_version)
+        object.__setattr__(self, "environments", environments)
+        object.__setattr__(self, "requires_python", requires_python)
+        object.__setattr__(self, "extras", extras)
+        object.__setattr__(self, "dependency_groups", dependency_groups)
+        object.__setattr__(self, "default_groups", default_groups)
+        object.__setattr__(self, "created_by", created_by)
+        object.__setattr__(self, "packages", packages)
+        object.__setattr__(self, "tool", tool)
+
+    @classmethod
+    def _from_dict(cls, d: Mapping[str, Any]) -> Self:
+        pylock = cls(
+            lock_version=_get_required_as(d, str, Version, "lock-version"),
+            environments=_get_sequence_as(d, str, Marker, "environments"),
+            extras=_get_sequence_as(d, str, _validate_normalized_name, "extras"),
+            dependency_groups=_get_sequence(d, str, "dependency-groups"),
+            default_groups=_get_sequence(d, str, "default-groups"),
+            created_by=_get_required(d, str, "created-by"),
+            requires_python=_get_as(d, str, SpecifierSet, "requires-python"),
+            packages=_get_required_sequence_of_objects(d, Package, "packages"),
+            tool=_get(d, Mapping, "tool"),  # type: ignore[type-abstract]
+        )
+        if not Version("1") <= pylock.lock_version < Version("2"):
+            raise PylockUnsupportedVersionError(
+                f"pylock version {pylock.lock_version} is not supported"
+            )
+        if pylock.lock_version > Version("1.0"):
+            _logger.warning(
+                "pylock minor version %s is not supported", pylock.lock_version
+            )
+        return pylock
+
+    @classmethod
+    def from_dict(cls, d: Mapping[str, Any], /) -> Self:
+        """Create and validate a Pylock instance from a TOML dictionary.
+
+        Raises :class:`PylockValidationError` if the input data is not
+        spec-compliant.
+        """
+        return cls._from_dict(d)
+
+    def to_dict(self) -> Mapping[str, Any]:
+        """Convert the Pylock instance to a TOML dictionary."""
+        return dataclasses.asdict(self, dict_factory=_toml_dict_factory)
+
+    def validate(self) -> None:
+        """Validate the Pylock instance against the specification.
+
+        Raises :class:`PylockValidationError` otherwise."""
+        self.from_dict(self.to_dict())
diff --git a/contrib/python/packaging/py3/packaging/requirements.py b/contrib/python/packaging/py3/packaging/requirements.py
index 4e068c9567d..3079be69bf8 100644
--- a/contrib/python/packaging/py3/packaging/requirements.py
+++ b/contrib/python/packaging/py3/packaging/requirements.py
@@ -3,7 +3,7 @@
 # for complete details.
 from __future__ import annotations
 
-from typing import Any, Iterator
+from typing import Iterator
 
 from ._parser import parse_requirement as _parse_requirement
 from ._tokenizer import ParserSyntaxError
@@ -57,7 +57,7 @@ class Requirement:
             yield str(self.specifier)
 
         if self.url:
-            yield f"@ {self.url}"
+            yield f" @ {self.url}"
             if self.marker:
                 yield " "
 
@@ -68,17 +68,12 @@ class Requirement:
         return "".join(self._iter_parts(self.name))
 
     def __repr__(self) -> str:
-        return f"<Requirement('{self}')>"
+        return f"<{self.__class__.__name__}('{self}')>"
 
     def __hash__(self) -> int:
-        return hash(
-            (
-                self.__class__.__name__,
-                *self._iter_parts(canonicalize_name(self.name)),
-            )
-        )
+        return hash(tuple(self._iter_parts(canonicalize_name(self.name))))
 
-    def __eq__(self, other: Any) -> bool:
+    def __eq__(self, other: object) -> bool:
         if not isinstance(other, Requirement):
             return NotImplemented
 
diff --git a/contrib/python/packaging/py3/packaging/specifiers.py b/contrib/python/packaging/py3/packaging/specifiers.py
index c8448043006..5d26b0d1ae2 100644
--- a/contrib/python/packaging/py3/packaging/specifiers.py
+++ b/contrib/python/packaging/py3/packaging/specifiers.py
@@ -13,22 +13,33 @@ from __future__ import annotations
 import abc
 import itertools
 import re
-from typing import Callable, Iterable, Iterator, TypeVar, Union
+from typing import Callable, Final, Iterable, Iterator, TypeVar, Union
 
 from .utils import canonicalize_version
-from .version import Version
+from .version import InvalidVersion, Version
 
 UnparsedVersion = Union[Version, str]
 UnparsedVersionVar = TypeVar("UnparsedVersionVar", bound=UnparsedVersion)
 CallableOperator = Callable[[Version, str], bool]
 
 
-def _coerce_version(version: UnparsedVersion) -> Version:
+def _coerce_version(version: UnparsedVersion) -> Version | None:
     if not isinstance(version, Version):
-        version = Version(version)
+        try:
+            version = Version(version)
+        except InvalidVersion:
+            return None
     return version
 
 
+def _public_version(version: Version) -> Version:
+    return version.__replace__(local=None)
+
+
+def _base_version(version: Version) -> Version:
+    return version.__replace__(pre=None, post=None, dev=None, local=None)
+
+
 class InvalidSpecifier(ValueError):
     """
     Raised when attempting to create a :class:`Specifier` with a specifier
@@ -42,6 +53,14 @@ class InvalidSpecifier(ValueError):
 
 
 class BaseSpecifier(metaclass=abc.ABCMeta):
+    __slots__ = ()
+    __match_args__ = ("_str",)
+
+    @property
+    def _str(self) -> str:
+        """Internal property for match_args"""
+        return str(self)
+
     @abc.abstractmethod
     def __str__(self) -> str:
         """
@@ -73,7 +92,7 @@ class BaseSpecifier(metaclass=abc.ABCMeta):
         prereleases or it can be set to ``None`` (the default) to use default semantics.
         """
 
-    @prereleases.setter
+    @prereleases.setter  # noqa: B027
     def prereleases(self, value: bool) -> None:
         """Setter for :attr:`prereleases`.
 
@@ -106,6 +125,8 @@ class Specifier(BaseSpecifier):
         comma-separated version specifiers (which is what package metadata contains).
     """
 
+    __slots__ = ("_prereleases", "_spec", "_spec_version")
+
     _operator_regex_str = r"""
         (?P<operator>(~=|==|!=|<=|>=|<|>|===))
         """
@@ -204,11 +225,11 @@ class Specifier(BaseSpecifier):
         """
 
     _regex = re.compile(
-        r"^\s*" + _operator_regex_str + _version_regex_str + r"\s*$",
+        r"\s*" + _operator_regex_str + _version_regex_str + r"\s*",
         re.VERBOSE | re.IGNORECASE,
     )
 
-    _operators = {
+    _operators: Final = {
         "~=": "compatible",
         "==": "equal",
         "!=": "not_equal",
@@ -232,7 +253,7 @@ class Specifier(BaseSpecifier):
         :raises InvalidSpecifier:
             If the given specifier is invalid (i.e. bad syntax).
         """
-        match = self._regex.search(spec)
+        match = self._regex.fullmatch(spec)
         if not match:
             raise InvalidSpecifier(f"Invalid specifier: {spec!r}")
 
@@ -244,33 +265,62 @@ class Specifier(BaseSpecifier):
         # Store whether or not this Specifier should accept prereleases
         self._prereleases = prereleases
 
-    # https://github.com/python/mypy/pull/13475#pullrequestreview-1079784515
-    @property  # type: ignore[override]
-    def prereleases(self) -> bool:
+        # Specifier version cache
+        self._spec_version: tuple[str, Version] | None = None
+
+    def _get_spec_version(self, version: str) -> Version | None:
+        """One element cache, as only one spec Version is needed per Specifier."""
+        if self._spec_version is not None and self._spec_version[0] == version:
+            return self._spec_version[1]
+
+        version_specifier = _coerce_version(version)
+        if version_specifier is None:
+            return None
+
+        self._spec_version = (version, version_specifier)
+        return version_specifier
+
+    def _require_spec_version(self, version: str) -> Version:
+        """Get spec version, asserting it's valid (not for === operator).
+
+        This method should only be called for operators where version
+        strings are guaranteed to be valid PEP 440 versions (not ===).
+        """
+        spec_version = self._get_spec_version(version)
+        assert spec_version is not None
+        return spec_version
+
+    @property
+    def prereleases(self) -> bool | None:
         # If there is an explicit prereleases set for this, then we'll just
         # blindly use that.
         if self._prereleases is not None:
             return self._prereleases
 
-        # Look at all of our specifiers and determine if they are inclusive
-        # operators, and if they are if they are including an explicit
-        # prerelease.
-        operator, version = self._spec
-        if operator in ["==", ">=", "<=", "~=", "===", ">", "<"]:
-            # The == specifier can include a trailing .*, if it does we
-            # want to remove before parsing.
-            if operator == "==" and version.endswith(".*"):
-                version = version[:-2]
+        # Only the "!=" operator does not imply prereleases when
+        # the version in the specifier is a prerelease.
+        operator, version_str = self._spec
+        if operator != "!=":
+            # The == specifier with trailing .* cannot include prereleases
+            # e.g. "==1.0a1.*" is not valid.
+            if operator == "==" and version_str.endswith(".*"):
+                return False
+
+            # "===" can have arbitrary string versions, so we cannot parse
+            # those, we take prereleases as unknown (None) for those.
+            version = self._get_spec_version(version_str)
+            if version is None:
+                return None
 
-            # Parse the version, and if it is a pre-release than this
-            # specifier allows pre-releases.
-            if Version(version).is_prerelease:
+            # For all other operators, use the check if spec Version
+            # object implies pre-releases.
+            if version.is_prerelease:
                 return True
 
         return False
 
     @prereleases.setter
-    def prereleases(self, value: bool) -> None:
+    def prereleases(self, value: bool | None) -> None:
         self._prereleases = value
 
     @property
@@ -321,11 +371,17 @@ class Specifier(BaseSpecifier):
 
     @property
     def _canonical_spec(self) -> tuple[str, str]:
+        operator, version = self._spec
+        if operator == "===" or version.endswith(".*"):
+            return operator, version
+
+        spec_version = self._require_spec_version(version)
+
         canonical_version = canonicalize_version(
-            self._spec[1],
-            strip_trailing_zero=(self._spec[0] != "~="),
+            spec_version, strip_trailing_zero=(operator != "~=")
         )
-        return self._spec[0], canonical_version
+
+        return operator, canonical_version
 
     def __hash__(self) -> int:
         return hash(self._canonical_spec)
@@ -390,7 +446,7 @@ class Specifier(BaseSpecifier):
         if spec.endswith(".*"):
             # In the case of prefix matching we want to ignore local segment.
             normalized_prospective = canonicalize_version(
-                prospective.public, strip_trailing_zero=False
+                _public_version(prospective), strip_trailing_zero=False
             )
             # Get the normalized version string ignoring the trailing .*
             normalized_spec = canonicalize_version(spec[:-2], strip_trailing_zero=False)
@@ -415,13 +471,13 @@ class Specifier(BaseSpecifier):
             return shortened_prospective == split_spec
         else:
             # Convert our spec string into a Version
-            spec_version = Version(spec)
+            spec_version = self._require_spec_version(spec)
 
             # If the specifier does not have a local segment, then we want to
             # act as if the prospective version also does not have a local
             # segment.
             if not spec_version.local:
-                prospective = Version(prospective.public)
+                prospective = _public_version(prospective)
 
             return prospective == spec_version
 
@@ -432,18 +488,18 @@ class Specifier(BaseSpecifier):
         # NB: Local version identifiers are NOT permitted in the version
         # specifier, so local version labels can be universally removed from
         # the prospective version.
-        return Version(prospective.public) <= Version(spec)
+        return _public_version(prospective) <= self._require_spec_version(spec)
 
     def _compare_greater_than_equal(self, prospective: Version, spec: str) -> bool:
         # NB: Local version identifiers are NOT permitted in the version
         # specifier, so local version labels can be universally removed from
         # the prospective version.
-        return Version(prospective.public) >= Version(spec)
+        return _public_version(prospective) >= self._require_spec_version(spec)
 
     def _compare_less_than(self, prospective: Version, spec_str: str) -> bool:
         # Convert our spec to a Version instance, since we'll want to work with
         # it as a version.
-        spec = Version(spec_str)
+        spec = self._require_spec_version(spec_str)
 
         # Check to see if the prospective version is less than the spec
         # version. If it's not we can short circuit and just return False now
@@ -455,9 +511,12 @@ class Specifier(BaseSpecifier):
         # includes is a pre-release version, that we do not accept pre-release
         # versions for the version mentioned in the specifier (e.g. <3.1 should
         # not match 3.1.dev0, but should match 3.0.dev0).
-        if not spec.is_prerelease and prospective.is_prerelease:
-            if Version(prospective.base_version) == Version(spec.base_version):
-                return False
+        if (
+            not spec.is_prerelease
+            and prospective.is_prerelease
+            and _base_version(prospective) == _base_version(spec)
+        ):
+            return False
 
         # If we've gotten to here, it means that prospective version is both
         # less than the spec version *and* it's not a pre-release of the same
@@ -467,7 +526,7 @@ class Specifier(BaseSpecifier):
     def _compare_greater_than(self, prospective: Version, spec_str: str) -> bool:
         # Convert our spec to a Version instance, since we'll want to work with
         # it as a version.
-        spec = Version(spec_str)
+        spec = self._require_spec_version(spec_str)
 
         # Check to see if the prospective version is greater than the spec
         # version. If it's not we can short circuit and just return False now
@@ -479,22 +538,26 @@ class Specifier(BaseSpecifier):
         # includes is a post-release version, that we do not accept
         # post-release versions for the version mentioned in the specifier
         # (e.g. >3.1 should not match 3.0.post0, but should match 3.2.post0).
-        if not spec.is_postrelease and prospective.is_postrelease:
-            if Version(prospective.base_version) == Version(spec.base_version):
-                return False
+        if (
+            not spec.is_postrelease
+            and prospective.is_postrelease
+            and _base_version(prospective) == _base_version(spec)
+        ):
+            return False
 
         # Ensure that we do not allow a local version of the version mentioned
         # in the specifier, which is technically greater than, to match.
-        if prospective.local is not None:
-            if Version(prospective.base_version) == Version(spec.base_version):
-                return False
+        if prospective.local is not None and _base_version(
+            prospective
+        ) == _base_version(spec):
+            return False
 
         # If we've gotten to here, it means that prospective version is both
         # greater than the spec version *and* it's not a pre-release of the
         # same version in the spec.
         return True
 
-    def _compare_arbitrary(self, prospective: Version, spec: str) -> bool:
+    def _compare_arbitrary(self, prospective: Version | str, spec: str) -> bool:
         return str(prospective).lower() == str(spec).lower()
 
     def __contains__(self, item: str | Version) -> bool:
@@ -512,7 +575,7 @@ class Specifier(BaseSpecifier):
         >>> "1.0.0" in Specifier(">=1.2.3")
         False
         >>> "1.3.0a1" in Specifier(">=1.2.3")
-        False
+        True
         >>> "1.3.0a1" in Specifier(">=1.2.3", prereleases=True)
         True
         """
@@ -526,8 +589,8 @@ class Specifier(BaseSpecifier):
             :class:`Version` instance.
         :param prereleases:
             Whether or not to match prereleases with this Specifier. If set to
-            ``None`` (the default), it uses :attr:`prereleases` to determine
-            whether or not prereleases are allowed.
+            ``None`` (the default), it will follow the recommendation from
+            :pep:`440` and match prereleases, as there are no other versions.
 
         >>> Specifier(">=1.2.3").contains("1.2.3")
         True
@@ -536,31 +599,14 @@ class Specifier(BaseSpecifier):
         >>> Specifier(">=1.2.3").contains("1.0.0")
         False
         >>> Specifier(">=1.2.3").contains("1.3.0a1")
-        False
-        >>> Specifier(">=1.2.3", prereleases=True).contains("1.3.0a1")
         True
-        >>> Specifier(">=1.2.3").contains("1.3.0a1", prereleases=True)
+        >>> Specifier(">=1.2.3", prereleases=False).contains("1.3.0a1")
+        False
+        >>> Specifier(">=1.2.3").contains("1.3.0a1")
         True
         """
 
-        # Determine if prereleases are to be allowed or not.
-        if prereleases is None:
-            prereleases = self.prereleases
-
-        # Normalize item to a Version, this allows us to have a shortcut for
-        # "2.0" in Specifier(">=2")
-        normalized_item = _coerce_version(item)
-
-        # Determine if we should be supporting prereleases in this specifier
-        # or not, if we do not support prereleases than we can short circuit
-        # logic if this version is a prereleases.
-        if normalized_item.is_prerelease and not prereleases:
-            return False
-
-        # Actually do the comparison to determine if this item is contained
-        # within this Specifier or not.
-        operator_callable: CallableOperator = self._get_operator(self.operator)
-        return operator_callable(normalized_item, self.version)
+        return bool(list(self.filter([item], prereleases=prereleases)))
 
     def filter(
         self, iterable: Iterable[UnparsedVersionVar], prereleases: bool | None = None
@@ -572,13 +618,8 @@ class Specifier(BaseSpecifier):
             The items in the iterable will be filtered according to the specifier.
         :param prereleases:
             Whether or not to allow prereleases in the returned iterator. If set to
-            ``None`` (the default), it will be intelligently decide whether to allow
-            prereleases or not (based on the :attr:`prereleases` attribute, and
-            whether the only versions matching are prereleases).
-
-        This method is smarter than just ``filter(Specifier().contains, [...])``
-        because it implements the rule from :pep:`440` that a prerelease item
-        SHOULD be accepted if no other versions match the given specifier.
+            ``None`` (the default), it will follow the recommendation from :pep:`440`
+            and match prereleases if there are no other versions.
 
         >>> list(Specifier(">=1.2.3").filter(["1.2", "1.3", "1.5a1"]))
         ['1.3']
@@ -591,40 +632,46 @@ class Specifier(BaseSpecifier):
         >>> list(Specifier(">=1.2.3", prereleases=True).filter(["1.3", "1.5a1"]))
         ['1.3', '1.5a1']
         """
+        prereleases_versions = []
+        found_non_prereleases = False
 
-        yielded = False
-        found_prereleases = []
+        # Determine if to include prereleases by default
+        include_prereleases = (
+            prereleases if prereleases is not None else self.prereleases
+        )
 
-        kw = {"prereleases": prereleases if prereleases is not None else True}
+        # Get the matching operator
+        operator_callable = self._get_operator(self.operator)
 
-        # Attempt to iterate over all the values in the iterable and if any of
-        # them match, yield them.
+        # Filter versions
         for version in iterable:
             parsed_version = _coerce_version(version)
-
-            if self.contains(parsed_version, **kw):
-                # If our version is a prerelease, and we were not set to allow
-                # prereleases, then we'll store it for later in case nothing
-                # else matches this specifier.
-                if parsed_version.is_prerelease and not (
-                    prereleases or self.prereleases
+            if parsed_version is None:
+                # === operator can match arbitrary (non-version) strings
+                if self.operator == "===" and self._compare_arbitrary(
+                    version, self.version
                 ):
-                    found_prereleases.append(version)
-                # Either this is not a prerelease, or we should have been
-                # accepting prereleases from the beginning.
-                else:
-                    yielded = True
                     yield version
+            elif operator_callable(parsed_version, self.version):
+                # If it's not a prerelease or prereleases are allowed, yield it directly
+                if not parsed_version.is_prerelease or include_prereleases:
+                    found_non_prereleases = True
+                    yield version
+                # Otherwise collect prereleases for potential later use
+                elif prereleases is None and self._prereleases is not False:
+                    prereleases_versions.append(version)
 
-        # Now that we've iterated over everything, determine if we've yielded
-        # any values, and if we have not and we have any prereleases stored up
-        # then we will go ahead and yield the prereleases.
-        if not yielded and found_prereleases:
-            for version in found_prereleases:
-                yield version
+        # If no non-prereleases were found and prereleases weren't
+        # explicitly forbidden, yield the collected prereleases
+        if (
+            not found_non_prereleases
+            and prereleases is None
+            and self._prereleases is not False
+        ):
+            yield from prereleases_versions
 
 
-_prefix_regex = re.compile(r"^([0-9]+)((?:a|b|c|rc)[0-9]+)$")
+_prefix_regex = re.compile(r"([0-9]+)((?:a|b|c|rc)[0-9]+)")
 
 
 def _version_split(version: str) -> list[str]:
@@ -641,7 +688,7 @@ def _version_split(version: str) -> list[str]:
     result.append(epoch or "0")
 
     for item in rest.split("."):
-        match = _prefix_regex.search(item)
+        match = _prefix_regex.fullmatch(item)
         if match:
             result.extend(match.groups())
         else:
@@ -694,6 +741,8 @@ class SpecifierSet(BaseSpecifier):
     specifiers (``>=3.0,!=3.1``), or no specifier at all.
     """
 
+    __slots__ = ("_prereleases", "_specs")
+
     def __init__(
         self,
         specifiers: str | Iterable[Specifier] = "",
@@ -747,10 +796,13 @@ class SpecifierSet(BaseSpecifier):
 
         # Otherwise we'll see if any of the given specifiers accept
         # prereleases, if any of them do we'll return True, otherwise False.
-        return any(s.prereleases for s in self._specs)
+        if any(s.prereleases for s in self._specs):
+            return True
+
+        return None
 
     @prereleases.setter
-    def prereleases(self, value: bool) -> None:
+    def prereleases(self, value: bool | None) -> None:
         self._prereleases = value
 
     def __repr__(self) -> str:
@@ -810,9 +862,9 @@ class SpecifierSet(BaseSpecifier):
 
         if self._prereleases is None and other._prereleases is not None:
             specifier._prereleases = other._prereleases
-        elif self._prereleases is not None and other._prereleases is None:
-            specifier._prereleases = self._prereleases
-        elif self._prereleases == other._prereleases:
+        elif (
+            self._prereleases is not None and other._prereleases is None
+        ) or self._prereleases == other._prereleases:
             specifier._prereleases = self._prereleases
         else:
             raise ValueError(
@@ -876,7 +928,7 @@ class SpecifierSet(BaseSpecifier):
         >>> "1.0.1" in SpecifierSet(">=1.0.0,!=1.0.1")
         False
         >>> "1.3.0a1" in SpecifierSet(">=1.0.0,!=1.0.1")
-        False
+        True
         >>> "1.3.0a1" in SpecifierSet(">=1.0.0,!=1.0.1", prereleases=True)
         True
         """
@@ -895,8 +947,11 @@ class SpecifierSet(BaseSpecifier):
             :class:`Version` instance.
         :param prereleases:
             Whether or not to match prereleases with this SpecifierSet. If set to
-            ``None`` (the default), it uses :attr:`prereleases` to determine
-            whether or not prereleases are allowed.
+            ``None`` (the default), it will follow the recommendation from :pep:`440`
+            and match prereleases, as there are no other versions.
+        :param installed:
+            Whether or not the item is installed. If set to ``True``, it will
+            accept prerelease versions even if the specifier does not allow them.
 
         >>> SpecifierSet(">=1.0.0,!=1.0.1").contains("1.2.3")
         True
@@ -905,39 +960,19 @@ class SpecifierSet(BaseSpecifier):
         >>> SpecifierSet(">=1.0.0,!=1.0.1").contains("1.0.1")
         False
         >>> SpecifierSet(">=1.0.0,!=1.0.1").contains("1.3.0a1")
-        False
-        >>> SpecifierSet(">=1.0.0,!=1.0.1", prereleases=True).contains("1.3.0a1")
         True
+        >>> SpecifierSet(">=1.0.0,!=1.0.1", prereleases=False).contains("1.3.0a1")
+        False
         >>> SpecifierSet(">=1.0.0,!=1.0.1").contains("1.3.0a1", prereleases=True)
         True
         """
-        # Ensure that our item is a Version instance.
-        if not isinstance(item, Version):
-            item = Version(item)
-
-        # Determine if we're forcing a prerelease or not, if we're not forcing
-        # one for this particular filter call, then we'll use whatever the
-        # SpecifierSet thinks for whether or not we should support prereleases.
-        if prereleases is None:
-            prereleases = self.prereleases
-
-        # We can determine if we're going to allow pre-releases by looking to
-        # see if any of the underlying items supports them. If none of them do
-        # and this item is a pre-release then we do not allow it and we can
-        # short circuit that here.
-        # Note: This means that 1.0.dev1 would not be contained in something
-        #       like >=1.0.devabc however it would be in >=1.0.debabc,>0.0.dev0
-        if not prereleases and item.is_prerelease:
-            return False
+        version = _coerce_version(item)
 
-        if installed and item.is_prerelease:
-            item = Version(item.base_version)
+        if version is not None and installed and version.is_prerelease:
+            prereleases = True
 
-        # We simply dispatch to the underlying specs here to make sure that the
-        # given version is contained within all of them.
-        # Note: This use of all() here means that an empty set of specifiers
-        #       will always return True, this is an explicit design decision.
-        return all(s.contains(item, prereleases=prereleases) for s in self._specs)
+        check_item = item if version is None else version
+        return bool(list(self.filter([check_item], prereleases=prereleases)))
 
     def filter(
         self, iterable: Iterable[UnparsedVersionVar], prereleases: bool | None = None
@@ -949,20 +984,15 @@ class SpecifierSet(BaseSpecifier):
             The items in the iterable will be filtered according to the specifier.
         :param prereleases:
             Whether or not to allow prereleases in the returned iterator. If set to
-            ``None`` (the default), it will be intelligently decide whether to allow
-            prereleases or not (based on the :attr:`prereleases` attribute, and
-            whether the only versions matching are prereleases).
-
-        This method is smarter than just ``filter(SpecifierSet(...).contains, [...])``
-        because it implements the rule from :pep:`440` that a prerelease item
-        SHOULD be accepted if no other versions match the given specifier.
+            ``None`` (the default), it will follow the recommendation from :pep:`440`
+            and match prereleases if there are no other versions.
 
         >>> list(SpecifierSet(">=1.2.3").filter(["1.2", "1.3", "1.5a1"]))
         ['1.3']
         >>> list(SpecifierSet(">=1.2.3").filter(["1.2", "1.3", Version("1.4")]))
         ['1.3', <Version('1.4')>]
         >>> list(SpecifierSet(">=1.2.3").filter(["1.2", "1.5a1"]))
-        []
+        ['1.5a1']
         >>> list(SpecifierSet(">=1.2.3").filter(["1.3", "1.5a1"], prereleases=True))
         ['1.3', '1.5a1']
         >>> list(SpecifierSet(">=1.2.3", prereleases=True).filter(["1.3", "1.5a1"]))
@@ -983,37 +1013,56 @@ class SpecifierSet(BaseSpecifier):
         # Determine if we're forcing a prerelease or not, if we're not forcing
         # one for this particular filter call, then we'll use whatever the
         # SpecifierSet thinks for whether or not we should support prereleases.
-        if prereleases is None:
+        if prereleases is None and self.prereleases is not None:
             prereleases = self.prereleases
 
         # If we have any specifiers, then we want to wrap our iterable in the
         # filter method for each one, this will act as a logical AND amongst
         # each specifier.
         if self._specs:
+            # When prereleases is None, we need to let all versions through
+            # the individual filters, then decide about prereleases at the end
+            # based on whether any non-prereleases matched ALL specs.
             for spec in self._specs:
-                iterable = spec.filter(iterable, prereleases=bool(prereleases))
-            return iter(iterable)
-        # If we do not have any specifiers, then we need to have a rough filter
-        # which will filter out any pre-releases, unless there are no final
-        # releases.
+                iterable = spec.filter(
+                    iterable, prereleases=True if prereleases is None else prereleases
+                )
+
+            if prereleases is not None:
+                # If we have a forced prereleases value,
+                # we can immediately return the iterator.
+                return iter(iterable)
         else:
-            filtered: list[UnparsedVersionVar] = []
-            found_prereleases: list[UnparsedVersionVar] = []
+            # Handle empty SpecifierSet cases where prereleases is not None.
+            if prereleases is True:
+                return iter(iterable)
 
-            for item in iterable:
-                parsed_version = _coerce_version(item)
+            if prereleases is False:
+                return (
+                    item
+                    for item in iterable
+                    if (version := _coerce_version(item)) is None
+                    or not version.is_prerelease
+                )
 
-                # Store any item which is a pre-release for later unless we've
-                # already found a final version or we are accepting prereleases
-                if parsed_version.is_prerelease and not prereleases:
-                    if not filtered:
-                        found_prereleases.append(item)
-                else:
-                    filtered.append(item)
+        # Finally if prereleases is None, apply PEP 440 logic:
+        # exclude prereleases unless there are no final releases that matched.
+        filtered_items: list[UnparsedVersionVar] = []
+        found_prereleases: list[UnparsedVersionVar] = []
+        found_final_release = False
 
-            # If we've found no items except for pre-releases, then we'll go
-            # ahead and use the pre-releases
-            if not filtered and found_prereleases and prereleases is None:
-                return iter(found_prereleases)
+        for item in iterable:
+            parsed_version = _coerce_version(item)
+            # Arbitrary strings are always included as it is not
+            # possible to determine if they are prereleases,
+            # and they have already passed all specifiers.
+            if parsed_version is None:
+                filtered_items.append(item)
+                found_prereleases.append(item)
+            elif parsed_version.is_prerelease:
+                found_prereleases.append(item)
+            else:
+                filtered_items.append(item)
+                found_final_release = True
 
-            return iter(filtered)
+        return iter(filtered_items if found_final_release else found_prereleases)
diff --git a/contrib/python/packaging/py3/packaging/tags.py b/contrib/python/packaging/py3/packaging/tags.py
index 8522f59c4f2..5ef27c897a4 100644
--- a/contrib/python/packaging/py3/packaging/tags.py
+++ b/contrib/python/packaging/py3/packaging/tags.py
@@ -13,6 +13,7 @@ import sys
 import sysconfig
 from importlib.machinery import EXTENSION_SUFFIXES
 from typing import (
+    Any,
     Iterable,
     Iterator,
     Sequence,
@@ -92,6 +93,13 @@ class Tag:
     def __repr__(self) -> str:
         return f"<{self} @ {id(self)}>"
 
+    def __setstate__(self, state: tuple[None, dict[str, Any]]) -> None:
+        # The cached _hash is wrong when unpickling.
+        _, slots = state
+        for k, v in slots.items():
+            setattr(self, k, v)
+        self._hash = hash((self._interpreter, self._abi, self._platform))
+
 
 def parse_tag(tag: str) -> frozenset[Tag]:
     """
@@ -209,16 +217,13 @@ def cpython_tags(
     interpreter = f"cp{_version_nodot(python_version[:2])}"
 
     if abis is None:
-        if len(python_version) > 1:
-            abis = _cpython_abis(python_version, warn)
-        else:
-            abis = []
+        abis = _cpython_abis(python_version, warn) if len(python_version) > 1 else []
     abis = list(abis)
     # 'abi3' and 'none' are explicitly handled later.
     for explicit_abi in ("abi3", "none"):
         try:
             abis.remove(explicit_abi)
-        except ValueError:
+        except ValueError:  # noqa: PERF203
             pass
 
     platforms = list(platforms or platform_tags())
@@ -299,11 +304,8 @@ def generic_tags(
     if not interpreter:
         interp_name = interpreter_name()
         interp_version = interpreter_version(warn=warn)
-        interpreter = "".join([interp_name, interp_version])
-    if abis is None:
-        abis = _generic_abi()
-    else:
-        abis = list(abis)
+        interpreter = f"{interp_name}{interp_version}"
+    abis = _generic_abi() if abis is None else list(abis)
     platforms = list(platforms or platform_tags())
     if "none" not in abis:
         abis.append("none")
@@ -424,14 +426,11 @@ def mac_platforms(
                 text=True,
             ).stdout
             version = cast("AppleVersion", tuple(map(int, version_str.split(".")[:2])))
-    else:
-        version = version
+
     if arch is None:
         arch = _mac_arch(cpu_arch)
-    else:
-        arch = arch
 
-    if (10, 0) <= version and version < (11, 0):
+    if (10, 0) <= version < (11, 0):
         # Prior to Mac OS 11, each yearly release of Mac OS bumped the
         # "minor" version number.  The major version was always 10.
         major_version = 10
@@ -622,11 +621,7 @@ def interpreter_version(*, warn: bool = False) -> str:
     Returns the version of the running interpreter.
     """
     version = _get_config_var("py_version_nodot", warn=warn)
-    if version:
-        version = str(version)
-    else:
-        version = _version_nodot(sys.version_info[:2])
-    return version
+    return str(version) if version else _version_nodot(sys.version_info[:2])
 
 
 def _version_nodot(version: PythonVersion) -> str:
diff --git a/contrib/python/packaging/py3/packaging/utils.py b/contrib/python/packaging/py3/packaging/utils.py
index 23450953df7..c41c8137f26 100644
--- a/contrib/python/packaging/py3/packaging/utils.py
+++ b/contrib/python/packaging/py3/packaging/utils.py
@@ -4,7 +4,6 @@
 
 from __future__ import annotations
 
-import functools
 import re
 from typing import NewType, Tuple, Union, cast
 
@@ -34,28 +33,29 @@ class InvalidSdistFilename(ValueError):
 
 
 # Core metadata spec for `Name`
-_validate_regex = re.compile(
-    r"^([A-Z0-9]|[A-Z0-9][A-Z0-9._-]*[A-Z0-9])$", re.IGNORECASE
-)
-_canonicalize_regex = re.compile(r"[-_.]+")
-_normalized_regex = re.compile(r"^([a-z0-9]|[a-z0-9]([a-z0-9-](?!--))*[a-z0-9])$")
+_validate_regex = re.compile(r"[A-Z0-9]|[A-Z0-9][A-Z0-9._-]*[A-Z0-9]", re.IGNORECASE)
+_normalized_regex = re.compile(r"[a-z0-9]|[a-z0-9]([a-z0-9-](?!--))*[a-z0-9]")
 # PEP 427: The build number must start with a digit.
 _build_tag_regex = re.compile(r"(\d+)(.*)")
 
 
 def canonicalize_name(name: str, *, validate: bool = False) -> NormalizedName:
-    if validate and not _validate_regex.match(name):
+    if validate and not _validate_regex.fullmatch(name):
         raise InvalidName(f"name is invalid: {name!r}")
-    # This is taken from PEP 503.
-    value = _canonicalize_regex.sub("-", name).lower()
-    return cast(NormalizedName, value)
+    # Ensure all ``.`` and ``_`` are ``-``
+    # Emulates ``re.sub(r"[-_.]+", "-", name).lower()`` from PEP 503
+    # Much faster than re, and even faster than str.translate
+    value = name.lower().replace("_", "-").replace(".", "-")
+    # Condense repeats (faster than regex)
+    while "--" in value:
+        value = value.replace("--", "-")
+    return cast("NormalizedName", value)
 
 
 def is_normalized_name(name: str) -> bool:
-    return _normalized_regex.match(name) is not None
+    return _normalized_regex.fullmatch(name) is not None
 
 
[email protected]
 def canonicalize_version(
     version: Version | str, *, strip_trailing_zero: bool = True
 ) -> str:
@@ -78,17 +78,12 @@ def canonicalize_version(
     >>> canonicalize_version('foo bar baz')
     'foo bar baz'
     """
-    return str(_TrimmedRelease(str(version)) if strip_trailing_zero else version)
-
-
-@canonicalize_version.register
-def _(version: str, *, strip_trailing_zero: bool = True) -> str:
-    try:
-        parsed = Version(version)
-    except InvalidVersion:
-        # Legacy versions cannot be normalized
-        return version
-    return canonicalize_version(parsed, strip_trailing_zero=strip_trailing_zero)
+    if isinstance(version, str):
+        try:
+            version = Version(version)
+        except InvalidVersion:
+            return str(version)
+    return str(_TrimmedRelease(version) if strip_trailing_zero else version)
 
 
 def parse_wheel_filename(
@@ -127,7 +122,7 @@ def parse_wheel_filename(
             raise InvalidWheelFilename(
                 f"Invalid build number: {build_part} in {filename!r}"
             )
-        build = cast(BuildTag, (int(build_match.group(1)), build_match.group(2)))
+        build = cast("BuildTag", (int(build_match.group(1)), build_match.group(2)))
     else:
         build = ()
     tags = parse_tag(parts[-1])
diff --git a/contrib/python/packaging/py3/packaging/version.py b/contrib/python/packaging/py3/packaging/version.py
index c9bbda20e46..1206c462d4f 100644
--- a/contrib/python/packaging/py3/packaging/version.py
+++ b/contrib/python/packaging/py3/packaging/version.py
@@ -9,12 +9,59 @@
 
 from __future__ import annotations
 
-import itertools
 import re
-from typing import Any, Callable, NamedTuple, SupportsInt, Tuple, Union
+import sys
+import typing
+from typing import (
+    Any,
+    Callable,
+    Literal,
+    NamedTuple,
+    SupportsInt,
+    Tuple,
+    TypedDict,
+    Union,
+)
 
 from ._structures import Infinity, InfinityType, NegativeInfinity, NegativeInfinityType
 
+if typing.TYPE_CHECKING:
+    from typing_extensions import Self, Unpack
+
+if sys.version_info >= (3, 13):  # pragma: no cover
+    from warnings import deprecated as _deprecated
+elif typing.TYPE_CHECKING:
+    from typing_extensions import deprecated as _deprecated
+else:  # pragma: no cover
+    import functools
+    import warnings
+
+    def _deprecated(message: str) -> object:
+        def decorator(func: object) -> object:
+            @functools.wraps(func)
+            def wrapper(*args: object, **kwargs: object) -> object:
+                warnings.warn(
+                    message,
+                    category=DeprecationWarning,
+                    stacklevel=2,
+                )
+                return func(*args, **kwargs)
+
+            return wrapper
+
+        return decorator
+
+
+_LETTER_NORMALIZATION = {
+    "alpha": "a",
+    "beta": "b",
+    "c": "rc",
+    "pre": "rc",
+    "preview": "rc",
+    "rev": "post",
+    "r": "post",
+}
+
 __all__ = ["VERSION_PATTERN", "InvalidVersion", "Version", "parse"]
 
 LocalType = Tuple[Union[int, str], ...]
@@ -35,13 +82,13 @@ CmpKey = Tuple[
 VersionComparisonMethod = Callable[[CmpKey, CmpKey], bool]
 
 
-class _Version(NamedTuple):
-    epoch: int
-    release: tuple[int, ...]
-    dev: tuple[str, int] | None
-    pre: tuple[str, int] | None
-    post: tuple[str, int] | None
-    local: LocalType | None
+class _VersionReplace(TypedDict, total=False):
+    epoch: int | None
+    release: tuple[int, ...] | None
+    pre: tuple[Literal["a", "b", "rc"], int] | None
+    post: int | None
+    dev: int | None
+    local: str | None
 
 
 def parse(version: str) -> Version:
@@ -67,7 +114,15 @@ class InvalidVersion(ValueError):
 
 
 class _BaseVersion:
-    _key: tuple[Any, ...]
+    __slots__ = ()
+
+    # This can also be a normal member (see the packaging_legacy package);
+    # we are just requiring it to be readable. Actually defining a property
+    # has runtime effect on subclasses, so it's typing only.
+    if typing.TYPE_CHECKING:
+
+        @property
+        def _key(self) -> tuple[Any, ...]: ...
 
     def __hash__(self) -> int:
         return hash(self._key)
@@ -114,38 +169,56 @@ class _BaseVersion:
 
 # Deliberately not anchored to the start and end of the string, to make it
 # easier for 3rd party code to reuse
+
+# Note that ++ doesn't behave identically on CPython and PyPy, so not using it here
 _VERSION_PATTERN = r"""
-    v?
+    v?+                                                   # optional leading v
     (?:
-        (?:(?P<epoch>[0-9]+)!)?                           # epoch
-        (?P<release>[0-9]+(?:\.[0-9]+)*)                  # release segment
+        (?:(?P<epoch>[0-9]+)!)?+                          # epoch
+        (?P<release>[0-9]+(?:\.[0-9]+)*+)                 # release segment
         (?P<pre>                                          # pre-release
-            [-_\.]?
+            [._-]?+
             (?P<pre_l>alpha|a|beta|b|preview|pre|c|rc)
-            [-_\.]?
+            [._-]?+
             (?P<pre_n>[0-9]+)?
-        )?
+        )?+
         (?P<post>                                         # post release
             (?:-(?P<post_n1>[0-9]+))
             |
             (?:
-                [-_\.]?
+                [._-]?
                 (?P<post_l>post|rev|r)
-                [-_\.]?
+                [._-]?
                 (?P<post_n2>[0-9]+)?
             )
-        )?
+        )?+
         (?P<dev>                                          # dev release
-            [-_\.]?
+            [._-]?+
             (?P<dev_l>dev)
-            [-_\.]?
+            [._-]?+
             (?P<dev_n>[0-9]+)?
-        )?
+        )?+
     )
-    (?:\+(?P<local>[a-z0-9]+(?:[-_\.][a-z0-9]+)*))?       # local version
+    (?:\+
+        (?P<local>                                        # local version
+            [a-z0-9]+
+            (?:[._-][a-z0-9]+)*+
+        )
+    )?+
 """
 
-VERSION_PATTERN = _VERSION_PATTERN
+_VERSION_PATTERN_OLD = _VERSION_PATTERN.replace("*+", "*").replace("?+", "?")
+
+# Possessive qualifiers were added in Python 3.11.
+# CPython 3.11.0-3.11.4 had a bug: https://github.com/python/cpython/pull/107795
+# Older PyPy also had a bug.
+VERSION_PATTERN = (
+    _VERSION_PATTERN_OLD
+    if (sys.implementation.name == "cpython" and sys.version_info < (3, 11, 5))
+    or (sys.implementation.name == "pypy" and sys.version_info < (3, 11, 13))
+    or sys.version_info < (3, 11)
+    else _VERSION_PATTERN
+)
 """
 A string containing the regular expression used to match a valid version.
 
@@ -158,6 +231,82 @@ flags set.
 """
 
 
+# Validation pattern for local version in replace()
+_LOCAL_PATTERN = re.compile(r"[a-z0-9]+(?:[._-][a-z0-9]+)*", re.IGNORECASE)
+
+
+def _validate_epoch(value: object, /) -> int:
+    epoch = value or 0
+    if isinstance(epoch, int) and epoch >= 0:
+        return epoch
+    msg = f"epoch must be non-negative integer, got {epoch}"
+    raise InvalidVersion(msg)
+
+
+def _validate_release(value: object, /) -> tuple[int, ...]:
+    release = (0,) if value is None else value
+    if (
+        isinstance(release, tuple)
+        and len(release) > 0
+        and all(isinstance(i, int) and i >= 0 for i in release)
+    ):
+        return release
+    msg = f"release must be a non-empty tuple of non-negative integers, got {release}"
+    raise InvalidVersion(msg)
+
+
+def _validate_pre(value: object, /) -> tuple[Literal["a", "b", "rc"], int] | None:
+    if value is None:
+        return value
+    if (
+        isinstance(value, tuple)
+        and len(value) == 2
+        and value[0] in ("a", "b", "rc")
+        and isinstance(value[1], int)
+        and value[1] >= 0
+    ):
+        return value
+    msg = f"pre must be a tuple of ('a'|'b'|'rc', non-negative int), got {value}"
+    raise InvalidVersion(msg)
+
+
+def _validate_post(value: object, /) -> tuple[Literal["post"], int] | None:
+    if value is None:
+        return value
+    if isinstance(value, int) and value >= 0:
+        return ("post", value)
+    msg = f"post must be non-negative integer, got {value}"
+    raise InvalidVersion(msg)
+
+
+def _validate_dev(value: object, /) -> tuple[Literal["dev"], int] | None:
+    if value is None:
+        return value
+    if isinstance(value, int) and value >= 0:
+        return ("dev", value)
+    msg = f"dev must be non-negative integer, got {value}"
+    raise InvalidVersion(msg)
+
+
+def _validate_local(value: object, /) -> LocalType | None:
+    if value is None:
+        return value
+    if isinstance(value, str) and _LOCAL_PATTERN.fullmatch(value):
+        return _parse_local_version(value)
+    msg = f"local must be a valid version string, got {value!r}"
+    raise InvalidVersion(msg)
+
+
+# Backward compatibility for internals before 26.0. Do not use.
+class _Version(NamedTuple):
+    epoch: int
+    release: tuple[int, ...]
+    dev: tuple[str, int] | None
+    pre: tuple[str, int] | None
+    post: tuple[str, int] | None
+    local: LocalType | None
+
+
 class Version(_BaseVersion):
     """This class abstracts handling of a project's versions.
 
@@ -182,8 +331,19 @@ class Version(_BaseVersion):
     True
     """
 
-    _regex = re.compile(r"^\s*" + VERSION_PATTERN + r"\s*$", re.VERBOSE | re.IGNORECASE)
-    _key: CmpKey
+    __slots__ = ("_dev", "_epoch", "_key_cache", "_local", "_post", "_pre", "_release")
+    __match_args__ = ("_str",)
+
+    _regex = re.compile(r"\s*" + VERSION_PATTERN + r"\s*", re.VERBOSE | re.IGNORECASE)
+
+    _epoch: int
+    _release: tuple[int, ...]
+    _dev: tuple[str, int] | None
+    _pre: tuple[str, int] | None
+    _post: tuple[str, int] | None
+    _local: LocalType | None
+
+    _key_cache: CmpKey | None
 
     def __init__(self, version: str) -> None:
         """Initialize a Version object.
@@ -195,34 +355,86 @@ class Version(_BaseVersion):
             If the ``version`` does not conform to PEP 440 in any way then this
             exception will be raised.
         """
-
         # Validate the version and parse it into pieces
-        match = self._regex.search(version)
+        match = self._regex.fullmatch(version)
         if not match:
             raise InvalidVersion(f"Invalid version: {version!r}")
+        self._epoch = int(match.group("epoch")) if match.group("epoch") else 0
+        self._release = tuple(map(int, match.group("release").split(".")))
+        self._pre = _parse_letter_version(match.group("pre_l"), match.group("pre_n"))
+        self._post = _parse_letter_version(
+            match.group("post_l"), match.group("post_n1") or match.group("post_n2")
+        )
+        self._dev = _parse_letter_version(match.group("dev_l"), match.group("dev_n"))
+        self._local = _parse_local_version(match.group("local"))
+
+        # Key which will be used for sorting
+        self._key_cache = None
 
-        # Store the parsed out pieces of the version
-        self._version = _Version(
-            epoch=int(match.group("epoch")) if match.group("epoch") else 0,
-            release=tuple(int(i) for i in match.group("release").split(".")),
-            pre=_parse_letter_version(match.group("pre_l"), match.group("pre_n")),
-            post=_parse_letter_version(
-                match.group("post_l"), match.group("post_n1") or match.group("post_n2")
-            ),
-            dev=_parse_letter_version(match.group("dev_l"), match.group("dev_n")),
-            local=_parse_local_version(match.group("local")),
+    def __replace__(self, **kwargs: Unpack[_VersionReplace]) -> Self:
+        epoch = _validate_epoch(kwargs["epoch"]) if "epoch" in kwargs else self._epoch
+        release = (
+            _validate_release(kwargs["release"])
+            if "release" in kwargs
+            else self._release
         )
+        pre = _validate_pre(kwargs["pre"]) if "pre" in kwargs else self._pre
+        post = _validate_post(kwargs["post"]) if "post" in kwargs else self._post
+        dev = _validate_dev(kwargs["dev"]) if "dev" in kwargs else self._dev
+        local = _validate_local(kwargs["local"]) if "local" in kwargs else self._local
+
+        if (
+            epoch == self._epoch
+            and release == self._release
+            and pre == self._pre
+            and post == self._post
+            and dev == self._dev
+            and local == self._local
+        ):
+            return self
+
+        new_version = self.__class__.__new__(self.__class__)
+        new_version._key_cache = None
+        new_version._epoch = epoch
+        new_version._release = release
+        new_version._pre = pre
+        new_version._post = post
+        new_version._dev = dev
+        new_version._local = local
+
+        return new_version
+
+    @property
+    def _key(self) -> CmpKey:
+        if self._key_cache is None:
+            self._key_cache = _cmpkey(
+                self._epoch,
+                self._release,
+                self._pre,
+                self._post,
+                self._dev,
+                self._local,
+            )
+        return self._key_cache
 
-        # Generate a key which will be used for sorting
-        self._key = _cmpkey(
-            self._version.epoch,
-            self._version.release,
-            self._version.pre,
-            self._version.post,
-            self._version.dev,
-            self._version.local,
+    @property
+    @_deprecated("Version._version is private and will be removed soon")
+    def _version(self) -> _Version:
+        return _Version(
+            self._epoch, self._release, self._dev, self._pre, self._post, self._local
         )
 
+    @_version.setter
+    @_deprecated("Version._version is private and will be removed soon")
+    def _version(self, value: _Version) -> None:
+        self._epoch = value.epoch
+        self._release = value.release
+        self._dev = value.dev
+        self._pre = value.pre
+        self._post = value.post
+        self._local = value.local
+        self._key_cache = None
+
     def __repr__(self) -> str:
         """A representation of the Version that shows all internal state.
 
@@ -237,32 +449,35 @@ class Version(_BaseVersion):
         >>> str(Version("1.0a5"))
         '1.0a5'
         """
-        parts = []
+        # This is a hot function, so not calling self.base_version
+        version = ".".join(map(str, self.release))
 
         # Epoch
-        if self.epoch != 0:
-            parts.append(f"{self.epoch}!")
-
-        # Release segment
-        parts.append(".".join(str(x) for x in self.release))
+        if self.epoch:
+            version = f"{self.epoch}!{version}"
 
         # Pre-release
         if self.pre is not None:
-            parts.append("".join(str(x) for x in self.pre))
+            version += "".join(map(str, self.pre))
 
         # Post-release
         if self.post is not None:
-            parts.append(f".post{self.post}")
+            version += f".post{self.post}"
 
         # Development release
         if self.dev is not None:
-            parts.append(f".dev{self.dev}")
+            version += f".dev{self.dev}"
 
         # Local version segment
         if self.local is not None:
-            parts.append(f"+{self.local}")
+            version += f"+{self.local}"
 
-        return "".join(parts)
+        return version
+
+    @property
+    def _str(self) -> str:
+        """Internal property for match_args"""
+        return str(self)
 
     @property
     def epoch(self) -> int:
@@ -273,7 +488,7 @@ class Version(_BaseVersion):
         >>> Version("1!2.0.0").epoch
         1
         """
-        return self._version.epoch
+        return self._epoch
 
     @property
     def release(self) -> tuple[int, ...]:
@@ -289,7 +504,7 @@ class Version(_BaseVersion):
         Includes trailing zeroes but not the epoch or any pre-release / development /
         post-release suffixes.
         """
-        return self._version.release
+        return self._release
 
     @property
     def pre(self) -> tuple[str, int] | None:
@@ -304,7 +519,7 @@ class Version(_BaseVersion):
         >>> Version("1.2.3rc1").pre
         ('rc', 1)
         """
-        return self._version.pre
+        return self._pre
 
     @property
     def post(self) -> int | None:
@@ -315,7 +530,7 @@ class Version(_BaseVersion):
         >>> Version("1.2.3.post1").post
         1
         """
-        return self._version.post[1] if self._version.post else None
+        return self._post[1] if self._post else None
 
     @property
     def dev(self) -> int | None:
@@ -326,7 +541,7 @@ class Version(_BaseVersion):
         >>> Version("1.2.3.dev1").dev
         1
         """
-        return self._version.dev[1] if self._version.dev else None
+        return self._dev[1] if self._dev else None
 
     @property
     def local(self) -> str | None:
@@ -337,8 +552,8 @@ class Version(_BaseVersion):
         >>> Version("1.2.3+abc").local
         'abc'
         """
-        if self._version.local:
-            return ".".join(str(x) for x in self._version.local)
+        if self._local:
+            return ".".join(str(x) for x in self._local)
         else:
             return None
 
@@ -369,16 +584,8 @@ class Version(_BaseVersion):
         The "base version" is the public version of the project without any pre or post
         release markers.
         """
-        parts = []
-
-        # Epoch
-        if self.epoch != 0:
-            parts.append(f"{self.epoch}!")
-
-        # Release segment
-        parts.append(".".join(str(x) for x in self.release))
-
-        return "".join(parts)
+        release_segment = ".".join(map(str, self.release))
+        return f"{self.epoch}!{release_segment}" if self.epoch else release_segment
 
     @property
     def is_prerelease(self) -> bool:
@@ -452,6 +659,20 @@ class Version(_BaseVersion):
 
 
 class _TrimmedRelease(Version):
+    __slots__ = ()
+
+    def __init__(self, version: str | Version) -> None:
+        if isinstance(version, Version):
+            self._epoch = version._epoch
+            self._release = version._release
+            self._dev = version._dev
+            self._pre = version._pre
+            self._post = version._post
+            self._local = version._local
+            self._key_cache = version._key_cache
+            return
+        super().__init__(version)  # pragma: no cover
+
     @property
     def release(self) -> tuple[int, ...]:
         """
@@ -462,45 +683,35 @@ class _TrimmedRelease(Version):
         >>> _TrimmedRelease('0.0').release
         (0,)
         """
+        # This leaves one 0.
         rel = super().release
-        nonzeros = (index for index, val in enumerate(rel) if val)
-        last_nonzero = max(nonzeros, default=0)
-        return rel[: last_nonzero + 1]
+        len_release = len(rel)
+        i = len_release
+        while i > 1 and rel[i - 1] == 0:
+            i -= 1
+        return rel if i == len_release else rel[:i]
 
 
 def _parse_letter_version(
     letter: str | None, number: str | bytes | SupportsInt | None
 ) -> tuple[str, int] | None:
     if letter:
-        # We consider there to be an implicit 0 in a pre-release if there is
-        # not a numeral associated with it.
-        if number is None:
-            number = 0
-
         # We normalize any letters to their lower case form
         letter = letter.lower()
 
         # We consider some words to be alternate spellings of other words and
         # in those cases we want to normalize the spellings to our preferred
         # spelling.
-        if letter == "alpha":
-            letter = "a"
-        elif letter == "beta":
-            letter = "b"
-        elif letter in ["c", "pre", "preview"]:
-            letter = "rc"
-        elif letter in ["rev", "r"]:
-            letter = "post"
+        letter = _LETTER_NORMALIZATION.get(letter, letter)
 
-        return letter, int(number)
+        # We consider there to be an implicit 0 in a pre-release if there is
+        # not a numeral associated with it.
+        return letter, int(number or 0)
 
-    assert not letter
     if number:
         # We assume if we are given a number, but we are not given a letter
         # then this is using the implicit post release syntax (e.g. 1.0-1)
-        letter = "post"
-
-        return letter, int(number)
+        return "post", int(number)
 
     return None
 
@@ -529,13 +740,12 @@ def _cmpkey(
     local: LocalType | None,
 ) -> CmpKey:
     # When we compare a release version, we want to compare it with all of the
-    # trailing zeros removed. So we'll use a reverse the list, drop all the now
-    # leading zeros until we come to something non zero, then take the rest
-    # re-reverse it back into the correct order and make it a tuple and use
-    # that for our sorting key.
-    _release = tuple(
-        reversed(list(itertools.dropwhile(lambda x: x == 0, reversed(release))))
-    )
+    # trailing zeros removed. We will use this for our sorting key.
+    len_release = len(release)
+    i = len_release
+    while i and release[i - 1] == 0:
+        i -= 1
+    _release = release if i == len_release else release[:i]
 
     # We need to "trick" the sorting algorithm to put 1.0.dev0 before 1.0a0.
     # We'll do this by abusing the pre segment, but we _only_ want to do this
diff --git a/contrib/python/packaging/py3/ya.make b/contrib/python/packaging/py3/ya.make
index 0e79cffb75a..6cc32b0d90f 100644
--- a/contrib/python/packaging/py3/ya.make
+++ b/contrib/python/packaging/py3/ya.make
@@ -2,7 +2,7 @@
 
 PY3_LIBRARY()
 
-VERSION(25.0)
+VERSION(26.0)
 
 LICENSE(BSD-2-Clause AND Apache-2.0)
 
@@ -21,6 +21,7 @@ PY_SRCS(
     packaging/licenses/_spdx.py
     packaging/markers.py
     packaging/metadata.py
+    packaging/pylock.py
     packaging/requirements.py
     packaging/specifiers.py
     packaging/tags.py