During seeding properly uninstall present versions of the wheels (#2186)

* During seeding remove dist-info for present versions of the wheels

An existing dist-info may contain entrypoints that may interfere with
normal functioning of the redeployed seeded wheel if there is a version
mismatch

fixes #2185

* Remove package directories from dist-info top_level packages
Remove other recorded files from RECORD
Remove dist-info itself

* Do not resolve paths prior to removal for symlink mode
In the test ensure the directories are compared as sets and not lists
Add setuptools downgrade to ensure proper cleanup of the existing version

* PR Feedback

Signed-off-by: Bernát Gábor <gaborjbernat@gmail.com>

Co-authored-by: Bernát Gábor <gaborjbernat@gmail.com>

3 files changed, 48 insertions, 8 deletions

diff --git a/docs/changelog/2185.bugfix.rst b/docs/changelog/2185.bugfix.rst
new file mode 100644
index 0000000..2b9921b
--- /dev/null
+++ b/docs/changelog/2185.bugfix.rst
@@ -0,0 +1,3 @@
+Fixed a bug where while creating a venv on top of an existing one, without cleaning, when seeded
+wheel version mismatch occurred, multiple ``.dist-info`` directories may be present, confounding entrypoint
+discovery - by :user:`arcivanov`
diff --git a/src/virtualenv/seed/embed/via_app_data/pip_install/base.py b/src/virtualenv/seed/embed/via_app_data/pip_install/base.py
index 017b7ef..35e0cca 100644
--- a/src/virtualenv/seed/embed/via_app_data/pip_install/base.py
+++ b/src/virtualenv/seed/embed/via_app_data/pip_install/base.py
@@ -5,6 +5,7 @@ import os
 import re
 import zipfile
 from abc import ABCMeta, abstractmethod
+from itertools import chain
 from tempfile import mkdtemp
 
 from distlib.scripts import ScriptMaker, enquote_executable
@@ -31,14 +32,10 @@ class PipInstall(object):
 
     def install(self, version_info):
         self._extracted = True
+        self._uninstall_previous_version()
         # sync image
         for filename in self._image_dir.iterdir():
             into = self._creator.purelib / filename.name
-            if into.exists():
-                if into.is_dir() and not into.is_symlink():
-                    safe_delete(into)
-                else:
-                    into.unlink()
             self._sync(filename, into)
         # generate console executables
         consoles = set()
@@ -150,6 +147,36 @@ class PipInstall(object):
         result.extend(Path(i) for i in new_files)
         return result
 
+    def _uninstall_previous_version(self):
+        dist_name = self._dist_info.stem.split("-")[0]
+        in_folders = chain.from_iterable([i.iterdir() for i in {self._creator.purelib, self._creator.platlib}])
+        paths = (p for p in in_folders if p.stem.split("-")[0] == dist_name and p.suffix == ".dist-info" and p.is_dir())
+        existing_dist = next(paths, None)
+        if existing_dist is not None:
+            self._uninstall_dist(existing_dist)
+
+    @staticmethod
+    def _uninstall_dist(dist):
+        dist_base = dist.parent
+        logging.debug("uninstall existing distribution %s from %s", dist.stem, dist_base)
+
+        top_txt = dist / "top_level.txt"  # add top level packages at folder level
+        paths = {dist.parent / i.strip() for i in top_txt.read_text().splitlines()} if top_txt.exists() else set()
+        paths.add(dist)  # add the dist-info folder itself
+
+        base_dirs, record = paths.copy(), dist / "RECORD"  # collect entries in record that we did not register yet
+        for name in (i.split(",")[0] for i in record.read_text().splitlines()) if record.exists() else ():
+            path = dist_base / name
+            if not any(p in base_dirs for p in path.parents):  # only add if not already added as a base dir
+                paths.add(path)
+
+        for path in sorted(paths):  # actually remove stuff in a stable order
+            if path.exists():
+                if path.is_dir() and not path.is_symlink():
+                    safe_delete(path)
+                else:
+                    path.unlink()
+
     def clear(self):
         if self._image_dir.exists():
             safe_delete(self._image_dir)
diff --git a/tests/unit/seed/embed/test_bootstrap_link_via_app_data.py b/tests/unit/seed/embed/test_bootstrap_link_via_app_data.py
index 37bc864..fdbd4d6 100644
--- a/tests/unit/seed/embed/test_bootstrap_link_via_app_data.py
+++ b/tests/unit/seed/embed/test_bootstrap_link_via_app_data.py
@@ -52,7 +52,7 @@ def test_seed_link_via_app_data(tmp_path, coverage_env, current_fastest, copies)
     pip = site_package / "pip"
     setuptools = site_package / "setuptools"
 
-    files_post_first_create = list(site_package.iterdir())
+    files_post_first_create = set(site_package.iterdir())
     assert pip in files_post_first_create
     assert setuptools in files_post_first_create
     for pip_exe in [
@@ -82,15 +82,25 @@ def test_seed_link_via_app_data(tmp_path, coverage_env, current_fastest, copies)
     assert not process.returncode
     assert site_package.exists()
 
-    files_post_first_uninstall = list(site_package.iterdir())
+    files_post_first_uninstall = set(site_package.iterdir())
     assert pip in files_post_first_uninstall
     assert setuptools not in files_post_first_uninstall
 
+    # install a different setuptools to test that virtualenv removes this before installing new
+    version = "setuptools<{}".format(bundle_ver["setuptools"].split("-")[1])
+    install_cmd = [str(result.creator.script("pip")), "--verbose", "--disable-pip-version-check", "install", version]
+    process = Popen(install_cmd)
+    process.communicate()
+    assert not process.returncode
+    assert site_package.exists()
+    files_post_downgrade = set(site_package.iterdir())
+    assert setuptools in files_post_downgrade
+
     # check we can run it again and will work - checks both overwrite and reuse cache
     result = cli_run(create_cmd)
     coverage_env()
     assert result
-    files_post_second_create = list(site_package.iterdir())
+    files_post_second_create = set(site_package.iterdir())
     assert files_post_first_create == files_post_second_create
 
     # Windows does not allow removing a executable while running it, so when uninstalling pip we need to do it via