pip_audit, test: handle invalid requires-python specifiers

CHANGELOG.md

@@ -8,6 +8,12 @@ All versions prior to 0.0.9 are untracked.
 
 ## [Unreleased]
 
+### Fixed
+
+* Fixed a crash triggered when a package specifies an invalid version
+  specifier for its `requires-python` version
+  ([#447](https://github.com/pypa/pip-audit/pull/447))
+
 ## [2.4.10]
 
 ### Fixed

pip_audit/_dependency_source/resolvelib/pypi_provider.py

@@ -8,6 +8,7 @@
 from __future__ import annotations
 
 import itertools
+import logging
 from email.message import EmailMessage, Message
 from email.parser import BytesParser
 from io import BytesIO
@@ -23,7 +24,7 @@
 import requests
 from cachecontrol import CacheControl
 from packaging.requirements import Requirement
-from packaging.specifiers import SpecifierSet
+from packaging.specifiers import InvalidSpecifier, SpecifierSet
 from packaging.utils import canonicalize_name, parse_sdist_filename, parse_wheel_filename
 from packaging.version import Version
 from resolvelib.providers import AbstractProvider
@@ -34,6 +35,8 @@
 from pip_audit._util import python_version
 from pip_audit._virtual_env import VirtualEnv, VirtualEnvError
 
+logger = logging.getLogger(__name__)
+
 # TODO: Final[Version] when our minimal Python is 3.8.
 PYTHON_VERSION: Version = python_version()
 
@@ -246,9 +249,19 @@ def get_project_from_index(
         py_req = i.attrib.get("data-requires-python")
         # Skip items that need a different Python version
         if py_req:
-            spec = SpecifierSet(py_req)
-            if PYTHON_VERSION not in spec:
-                continue
+            try:
+                # NOTE: Starting with packaging==22.0, specifier parsing is
+                # stricter: specifier components can only use the wildcard
+                # comparison syntax on exact comparison operators (== and !=),
+                # not on ordered operators like `>=`. There are existing
+                # packages that use the invalid syntax in their metadata
+                # however (like nltk==3.6, which does requires-python >= 3.5.*),
+                # so we follow pip`'s behavior and ignore these specifiers.
+                spec = SpecifierSet(py_req)
+                if PYTHON_VERSION not in spec:
+                    continue
+            except InvalidSpecifier:
+                logger.warning(f"invalid specifier set for Python version: {py_req}")
 
         path = parsed_dist_url.path
         filename = path.rpartition("/")[-1]

test/dependency_source/resolvelib/test_resolvelib.py

@@ -2,6 +2,7 @@
 
 from email.message import EmailMessage
 
+import pretend
 import pytest
 import requests
 from packaging.requirements import Requirement
@@ -221,6 +222,42 @@ def test_resolvelib_wheel_python_version(monkeypatch):
         dict(resolver.resolve_all(iter([req])))
 
 
+def test_resolvelib_wheel_python_version_invalid_specifier(monkeypatch):
+    # requires-python is meant to be a valid specifier version, but earlier
+    # versions of packaging allowed LegacyVersion parsing for invalid versions.
+    # This changed in packaging==22.0, so we follow pip's lead and ignore
+    # any Python version specifiers that aren't valid.
+    # Note that we intentionally test that version that *should* be skipped
+    # with a valid specifier (<=3.5.*) is instead included.
+    data = (
+        '<a href="https://files.pythonhosted.org/packages/54/4f/'
+        "1b294c1a4ab7b2ad5ca5fc4a9a65a22ef1ac48be126289d97668852d4ab3/Flask-2.0.1-py3-none-any.whl#"
+        'sha256=a6209ca15eb63fc9385f38e452704113d679511d9574d09b2cf9183ae7d20dc9" '
+        'data-requires-python="&lt;=3.5.*">Flask-2.0.1-py3-none-any.whl</a><br/>'
+    )
+
+    logger = pretend.stub(warning=pretend.call_recorder(lambda s: None))
+    monkeypatch.setattr(pypi_provider, "logger", logger)
+
+    monkeypatch.setattr(
+        pypi_provider.Candidate, "_get_metadata_for_wheel", lambda _: get_metadata_mock()
+    )
+
+    resolver = resolvelib.ResolveLibResolver()
+    monkeypatch.setattr(
+        resolver.provider.session, "get", lambda _url, **kwargs: get_package_mock(data)
+    )
+
+    req = Requirement("flask==2.0.1")
+    resolved_deps = dict(resolver.resolve_all(iter([req])))
+    assert req in resolved_deps
+    assert resolved_deps[req] == [ResolvedDependency("flask", Version("2.0.1"))]
+
+    assert logger.warning.calls == [
+        pretend.call("invalid specifier set for Python version: <=3.5.*")
+    ]
+
+
 def test_resolvelib_wheel_canonical_name_mismatch(monkeypatch):
     # Call the underlying wheel, Mask instead of Flask. This should throw an `ResolutionImpossible`
     # error.