Fix dup requirement extra merging during PEX boot.

CHANGES.md

@@ -1,5 +1,12 @@
 # Release Notes
 
+## 2.33.2
+
+This release fixes PEXes build with root requirements like `foo[bar] foo[baz]` (vs. `foo[bar,baz]`,
+which worked already).
+
+* Fix dup requirement extra merging during PEX boot. (#2707)
+
 ## 2.33.1
 
 This release fixes a bug in both `pex3 lock subset` and

pex/environment.py

@@ -177,6 +177,10 @@ class _QualifiedRequirement(object):
     requirement = attr.ib()  # type: Requirement
     required = attr.ib(default=True)  # type: bool
 
+    def with_extras(self, extras):
+        # type: (FrozenSet[str]) -> _QualifiedRequirement
+        return attr.evolve(self, requirement=attr.evolve(self.requirement, extras=extras))
+
 
 @attr.s(frozen=True)
 class _DistributionNotFound(object):
@@ -568,7 +572,20 @@ def _root_requirements_iter(
                     ),
                     V=9,
                 )
-            yield qualified_requirement
+
+            # We may have had multiple requirements that select the winning candidate distribution.
+            # For example, say we're a Python 3.10 interpreter and the root requirements are
+            # `"foo[bar]; python_version < '3.11'" "foo[baz]==1.2.3"`. In that case, we want to
+            # ensure that for whichever ~random requirement we selected as a representative we
+            # gather all extras across the candidate requirements to make sure all requested extras
+            # are grafted in to the resolve.
+            yield qualified_requirement.with_extras(
+                frozenset(
+                    itertools.chain.from_iterable(
+                        candidate[1].requirement.extras for candidate in candidates
+                    )
+                )
+            )
 
     def resolve(self):
         # type: () -> Iterable[Distribution]

pex/version.py

@@ -1,4 +1,4 @@
 # Copyright 2015 Pex project contributors.
 # Licensed under the Apache License, Version 2.0 (see LICENSE).
 
-__version__ = "2.33.1"
+__version__ = "2.33.2"

tests/integration/test_issue_2706.py

@@ -0,0 +1,72 @@
+# Copyright 2025 Pex project contributors.
+# Licensed under the Apache License, Version 2.0 (see LICENSE).
+
+from __future__ import absolute_import
+
+import shutil
+import subprocess
+
+from pex.cache.dirs import CacheDir
+from pex.common import safe_mkdir
+from pex.compatibility import commonpath
+from pex.pip.version import PipVersion
+from pex.venv.virtualenv import InstallationChoice, Virtualenv
+from testing import built_wheel, run_pex_command
+from testing.pytest_utils.tmp import Tempdir
+
+
+def test_extras_from_dup_root_reqs(tmpdir):
+    # type: (Tempdir) -> None
+
+    find_links = tmpdir.join("find-links")
+    safe_mkdir(find_links)
+
+    if PipVersion.DEFAULT is not PipVersion.VENDORED:
+        Virtualenv.create(
+            tmpdir.join("pip-resolver-venv"), install_pip=InstallationChoice.YES
+        ).interpreter.execute(
+            args=["-m", "pip", "wheel", "--wheel-dir", find_links]
+            + list(map(str, PipVersion.DEFAULT.requirements))
+        )
+
+    with built_wheel(
+        name="foo", extras_require={"bar": ["bar"], "baz": ["baz"]}
+    ) as foo, built_wheel(name="bar") as bar, built_wheel(name="baz") as baz:
+        shutil.copy(foo, find_links)
+        shutil.copy(bar, find_links)
+        shutil.copy(baz, find_links)
+
+        pex_root = tmpdir.join("pex_root")
+        pex = tmpdir.join("pex")
+        run_pex_command(
+            args=[
+                "--pex-root",
+                pex_root,
+                "--runtime-pex-root",
+                pex_root,
+                "--no-pypi",
+                "--find-links",
+                find_links,
+                "--resolver-version",
+                "pip-2020-resolver",
+                "foo[bar]",
+                "foo[baz]",
+                "-o",
+                pex,
+            ]
+        ).assert_success()
+
+        installed_wheel_dir = CacheDir.INSTALLED_WHEELS.path(pex_root=pex_root)
+        for module in "foo", "bar", "baz":
+            assert installed_wheel_dir == commonpath(
+                (
+                    installed_wheel_dir,
+                    subprocess.check_output(
+                        args=[
+                            pex,
+                            "-c",
+                            "import {module}; print({module}.__file__)".format(module=module),
+                        ]
+                    ).decode("utf-8"),
+                )
+            )