semver/pep508: handle wildcard exclusions

Prior to this change, when exporting PEP 508 strings for dependencies,
wildcard exclusion constraints like `!=2.0.*` were incorrectly
serialised as invalid PEP 508 due to how version unions were serialsed.

This change allows for determining if a version union is a single
wildcard range exclusion, and if so serialise it appropriately.

Resolves: python-poetry/poetry#5470

src/poetry/core/packages/dependency.py

@@ -260,7 +260,13 @@ def base_pep_508_name(self) -> str:
 
         constraint = self.constraint
         if isinstance(constraint, VersionUnion):
-            if constraint.excludes_single_version():
+            if (
+                constraint.excludes_single_version()
+                or constraint.excludes_single_wildcard_range()
+            ):
+                # This branch is a short-circuit logic for special cases and
+                # avoids having to split and parse constraint again. This has
+                # no functional difference with the logic in the else branch.
                 requirement += f" ({str(constraint)})"
             else:
                 constraints = self.pretty_constraint.split(",")

src/poetry/core/semver/version_union.py

@@ -238,6 +238,157 @@ def _ranges_for(
 
         raise ValueError(f"Unknown VersionConstraint type {constraint}")
 
+    def _exclude_single_wildcard_range_string(self) -> str:
+        """
+        Helper method to convert this instance into a wild card range
+        string.
+        """
+        if not self.excludes_single_wildcard_range():
+            raise ValueError("Not a valid wildcard range")
+
+        # we assume here that since it is a single exclusion range
+        # that it is one of "< 2.0.0 || >= 2.1.0" or ">= 2.1.0 || < 2.0.0"
+        # and the one with the max is the first part
+        idx_order = (0, 1) if self._ranges[0].max else (1, 0)
+        one = self._ranges[idx_order[0]].max
+        two = self._ranges[idx_order[1]].min
+
+        # versions can have both semver and non semver parts
+        parts_one = [
+            one.major,
+            one.minor or 0,
+            one.patch or 0,
+            *list(one.non_semver_parts or []),
+        ]
+        parts_two = [
+            two.major,
+            two.minor or 0,
+            two.patch or 0,
+            *list(two.non_semver_parts or []),
+        ]
+
+        # we assume here that a wildcard range implies that the part following the
+        # first part that is different in the second range is the wildcard, this means
+        # that multiple wildcards are not supported right now.
+        parts = []
+
+        for idx, part in enumerate(parts_one):
+            parts.append(str(part))
+            if parts_two[idx] != part:
+                # since this part is different the next one is the wildcard
+                # for example, "< 2.0.0 || >= 2.1.0" gets us a wildcard range
+                # 2.0.*
+                parts.append("*")
+                break
+        else:
+            # we should not ever get here, however it is likely that poorly
+            # constructed metadata exists
+            raise ValueError("Not a valid wildcard range")
+
+        return f"!={'.'.join(parts)}"
+
+    @staticmethod
+    def _excludes_single_wildcard_range_check_is_valid_range(
+        one: VersionRangeConstraint, two: VersionRangeConstraint
+    ) -> bool:
+        """
+        Helper method to determine if two versions define a single wildcard range.
+
+        In cases where !=2.0.* was parsed by us, the union is of the range
+        <2.0.0 || >=2.1.0. In user defined ranges, precision might be different.
+        For example, a union <2.0 || >= 2.1.0 is still !=2.0.*. In order to
+        handle these cases we make sure that if precisions do not match, extra
+        checks are performed to validate that the constraint is a valid single
+        wildcard range.
+        """
+
+        max_precision = max(one.max.precision, two.min.precision)
+
+        if max_precision <= 3:
+            # In cases where both versions have a precision less than 3,
+            # we can make use of the next major/minor/patch versions.
+            return two.min in {
+                one.max.next_major(),
+                one.max.next_minor(),
+                one.max.next_patch(),
+            }
+        else:
+            # When there are non-semver parts in one of the versions, we need to
+            # ensure we use zero padded version and in addition to next major/minor/
+            # patch versions, also check each next release for the extra parts.
+            from_parts = one.max.__class__.from_parts
+
+            _extras: list[list[int]] = []
+            _versions: list[Version] = []
+
+            for _version in [one.max, two.min]:
+                _extra = list(_version.non_semver_parts or [])
+
+                while len(_extra) < (max_precision - 3):
+                    # pad zeros for extra parts to ensure precisions are equal
+                    _extra.append(0)
+
+                # create a new release with unspecified parts padded with zeros
+                _padded_version: Version = from_parts(
+                    major=_version.major,
+                    minor=_version.minor or 0,
+                    patch=_version.patch or 0,
+                    extra=tuple(_extra),
+                )
+
+                _extras.append(_extra)
+                _versions.append(_padded_version)
+
+            _extra_one = _extras[0]
+            _padded_version_one = _versions[0]
+            _padded_version_two = _versions[1]
+
+            _check_versions = {
+                _padded_version_one.next_major(),
+                _padded_version_one.next_minor(),
+                _padded_version_one.next_patch(),
+            }
+
+            # for each non-semver (extra) part, bump a version
+            for idx in range(len(_extra_one)):
+                _extra = [
+                    *_extra_one[: idx - 1],
+                    (_extra_one[idx] + 1),
+                    *_extra_one[idx + 1 :],
+                ]
+                _check_versions.add(
+                    from_parts(
+                        _padded_version_one.major,
+                        _padded_version_one.minor,
+                        _padded_version_one.patch,
+                        *_extra,
+                    )
+                )
+
+            return _padded_version_two in _check_versions
+
+    def excludes_single_wildcard_range(self) -> bool:
+        from poetry.core.semver.version_range import VersionRange
+
+        if len(self._ranges) != 2:
+            return False
+
+        idx_order = (0, 1) if self._ranges[0].max else (1, 0)
+        one = self._ranges[idx_order[0]]
+        two = self._ranges[idx_order[1]]
+
+        is_range_exclusion = (
+            one.max and not one.include_max and two.min and two.include_min
+        )
+
+        if not is_range_exclusion:
+            return False
+
+        if not self._excludes_single_wildcard_range_check_is_valid_range(one, two):
+            return False
+
+        return isinstance(VersionRange().difference(self), VersionRange)
+
     def excludes_single_version(self) -> bool:
         from poetry.core.semver.version import Version
         from poetry.core.semver.version_range import VersionRange
@@ -264,7 +415,10 @@ def __str__(self) -> str:
         if self.excludes_single_version():
             return f"!={VersionRange().difference(self)}"
 
-        return " || ".join([str(r) for r in self._ranges])
+        try:
+            return self._exclude_single_wildcard_range_string()
+        except ValueError:
+            return " || ".join([str(r) for r in self._ranges])
 
     def __repr__(self) -> str:
         return f"<VersionUnion {str(self)}>"

tests/masonry/builders/fixtures/with_wildcard_dependency_constraint/pyproject.toml

@@ -0,0 +1,11 @@
+[tool.poetry]
+name = "my-package"
+version = "1.2.3"
+description = "Some description."
+authors = [
+    "People Everywhere <[email protected]>"
+]
+
+[tool.poetry.dependencies]
+python = "^3.10"
+google-api-python-client = ">=1.8,!=2.0.*"

tests/masonry/builders/test_builder.py

@@ -285,3 +285,15 @@ def test_metadata_with_readme_files() -> None:
     description = "\n".join([readme1.read_text(), readme2.read_text(), ""])
 
     assert metadata.get_payload() == description
+
+
+def test_metadata_with_wildcard_dependency_constraint() -> None:
+    test_path = (
+        Path(__file__).parent / "fixtures" / "with_wildcard_dependency_constraint"
+    )
+    builder = Builder(Factory().create_poetry(test_path))
+
+    metadata = Parser().parsestr(builder.get_metadata_content())
+
+    requires = metadata.get_all("Requires-Dist")
+    assert requires == ["google-api-python-client (>=1.8,!=2.0.*)"]

tests/packages/test_dependency.py

@@ -151,10 +151,18 @@ def test_to_pep_508_in_extras_parsed() -> None:
     assert result == "foo[bar,baz] (>=1.23,<2.0)"
 
 
-def test_to_pep_508_with_single_version_excluded() -> None:
-    dependency = Dependency("foo", "!=1.2.3")
+@pytest.mark.parametrize(
+    ("exclusion", "expected"),
+    [
+        ("!=1.2.3", "!=1.2.3"),
+        ("!=1.2.*", "!=1.2.*"),
+        ("<2.0 || >=2.1", "!=2.0.*"),
+    ],
+)
+def test_to_pep_508_with_excluded_versions(exclusion: str, expected: str) -> None:
+    dependency = Dependency("foo", exclusion)
 
-    assert dependency.to_pep_508() == "foo (!=1.2.3)"
+    assert dependency.to_pep_508() == f"foo ({expected})"
 
 
 @pytest.mark.parametrize(
@@ -245,6 +253,29 @@ def test_complete_name() -> None:
             ["x"],
             "A[x] (>=1.6.5,!=1.8.0,<3.1.0)",
         ),
+        # test single version range exclusions
+        ("A", ">=1.8,!=2.0.*", None, "A (>=1.8,!=2.0.*)"),
+        ("A", "!=0.0.*", None, "A (!=0.0.*)"),
+        ("A", "!=0.1.*", None, "A (!=0.1.*)"),
+        ("A", "!=0.*", None, "A (>=1.0.0)"),
+        ("A", ">=1.8,!=2.*", None, "A (>=1.8,!=2.*)"),
+        ("A", ">=1.8,!=2.*.*", None, "A (>=1.8,!=2.*)"),
+        ("A", ">=1.8,<2.0 || >=2.1.0", None, "A (>=1.8,!=2.0.*)"),
+        ("A", ">=1.8,<2.0.0 || >=3.0.0", None, "A (>=1.8,!=2.*)"),
+        ("A", ">=1.8,<2.0 || >=3", None, "A (>=1.8,!=2.*)"),
+        ("A", ">=1.8,<2 || >=2.1.0", None, "A (>=1.8,!=2.0.*)"),
+        ("A", ">=1.8,<2 || >=2.1", None, "A (>=1.8,!=2.0.*)"),
+        ("A", ">=1.8,!=2.0.*,!=3.0.*", None, "A (>=1.8,!=2.0.*,!=3.0.*)"),
+        ("A", ">=1.8.0.0,<2.0.0.0 || >=2.0.1.0", None, "A (>=1.8.0.0,!=2.0.0.*)"),
+        ("A", ">=1.8.0.0,<2 || >=2.0.1.0", None, "A (>=1.8.0.0,!=2.0.0.*)"),
+        # we verify that the range exclusion logic is not too eager
+        ("A", ">=1.8,<2.0 || >=2.2.0", None, "A (>=1.8,<2.0 || >=2.2.0)"),
+        ("A", ">=1.8,<2.0 || >=2.1.5", None, "A (>=1.8,<2.0 || >=2.1.5)"),
+        ("A", ">=1.8.0.0,<2 || >=2.0.1.5", None, "A (>=1.8.0.0,<2 || >=2.0.1.5)"),
+        # non-semver version test is ignored due to existing bug in wildcard
+        # constraint parsing that ignores non-semver versions
+        # TODO: re-enable for verification once fixed
+        # ("A", ">=1.8.0.0,!=2.0.0.*", None, "A (>=1.8.0.0,!=2.0.0.*)"),  # noqa: E800
     ],
 )
 def test_dependency_string_representation(