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 +260,10 @@ 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()
+            ):
                 requirement += f" ({str(constraint)})"
             else:
                 constraints = self.pretty_constraint.split(",")

src/poetry/core/semver/version_union.py

@@ -10,6 +10,7 @@
 
 if TYPE_CHECKING:
     from poetry.core.semver.version import Version
+    from poetry.core.version.pep440 import Release
 
 
 class VersionUnion(VersionConstraint):
@@ -238,6 +239,138 @@ def _ranges_for(
 
         raise ValueError(f"Unknown VersionConstraint type {constraint}")
 
+    def _exclude_single_wildcard_range_string(self) -> str:
+        """
+        Helper method to convert
+        """
+        if not self.excludes_single_wildcard_range():
+            raise ValueError("Version Union is not a single wildcard exclusion 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.release
+        two = self._ranges[idx_order[1]].min.release
+
+        # versions can have both semver and non semver parts
+        parts_one = [one.major, one.minor or 0, one.patch or 0, *list(one.extra or [])]
+        parts_two = [two.major, two.minor or 0, two.patch or 0, *list(two.extra 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)}"
+
+    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
+
+        # In cases where !=2.0.* was parsed by use, 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.
+
+        if one.max.release.precision != two.min.release.precision:
+            max_precision = max(one.max.release.precision, two.min.release.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.
+                if two.min not in {
+                    one.max.next_major(),
+                    one.max.next_minor(),
+                    one.max.next_patch(),
+                }:
+                    return False
+            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]] = []
+                _releases: list[Release] = []
+
+                for release in [one.max.release, two.min.release]:
+                    _extra = list(release.extra 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
+                    _release_expanded = from_parts(
+                        release.major,
+                        release.minor or 0,
+                        release.patch or 0,
+                        *_extra,
+                    )
+
+                    _extras.append(_extra)
+                    _releases.append(_release_expanded)
+
+                _extra_parts_one = _extras[0]
+                _release_expanded_one = _releases[0]
+                _release_expanded_two = _releases[1]
+
+                _check_versions = {
+                    _release_expanded_one.next_major(),
+                    _release_expanded_one.next_minor(),
+                    _release_expanded_one.next_patch(),
+                }
+
+                # for each extra part, bump a version
+                for idx in range(len(_extra_parts_one)):
+                    _extra = [
+                        *_extra_parts_one[: idx - 1],
+                        (_extra_parts_one[idx] + 1),
+                        *_extra_parts_one[idx + 1 :],
+                    ]
+                    _check_versions.add(
+                        from_parts(
+                            _release_expanded_one.major,
+                            _release_expanded_one.minor,
+                            _release_expanded_one.patch,
+                            *_extra,
+                        )
+                    )
+
+                if _release_expanded_two not in _check_versions:
+                    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 +397,10 @@ 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(