diff --git a/src/pip/_internal/cli/main_parser.py b/src/pip/_internal/cli/main_parser.py
index 5ade356b9..d07dfeab8 100644
--- a/src/pip/_internal/cli/main_parser.py
+++ b/src/pip/_internal/cli/main_parser.py
@@ -80,6 +80,11 @@ def parse_command(args: List[str]) -> Tuple[str, List[str]]:
 
     # --python
     if general_options.python and "_PIP_RUNNING_IN_SUBPROCESS" not in os.environ:
+        raise CommandError(
+            "--python option is not supported on Gentoo, as it requires bundled "
+            "dependencies that have been removed to improve security"
+        )
+
         # Re-invoke pip using the specified Python interpreter
         interpreter = identify_python_interpreter(general_options.python)
         if interpreter is None:
diff --git a/src/pip/_internal/commands/debug.py b/src/pip/_internal/commands/debug.py
index 567ca967e..427bfcf04 100644
--- a/src/pip/_internal/commands/debug.py
+++ b/src/pip/_internal/commands/debug.py
@@ -6,7 +6,6 @@ from optparse import Values
 from types import ModuleType
 from typing import Any, Dict, List, Optional
 
-import pip._vendor
 from pip._vendor.certifi import where
 from pip._vendor.packaging.version import parse as parse_version
 
@@ -192,9 +191,7 @@ class DebugCommand(Command):
         show_value("REQUESTS_CA_BUNDLE", os.environ.get("REQUESTS_CA_BUNDLE"))
         show_value("CURL_CA_BUNDLE", os.environ.get("CURL_CA_BUNDLE"))
         show_value("pip._vendor.certifi.where()", where())
-        show_value("pip._vendor.DEBUNDLED", pip._vendor.DEBUNDLED)
-
-        show_vendor_versions()
+        show_value("pip._vendor.DEBUNDLED", True)
 
         show_tags(options)
 
diff --git a/tests/conftest.py b/tests/conftest.py
index d093eea46..bf4d9e782 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -418,6 +418,7 @@ def _common_wheel_editable_install(
     )
     install_dir = tmpdir_factory.mktemp(package) / "install"
     lib_install_dir = install_dir / "lib"
+    return lib_install_dir
     bin_install_dir = install_dir / "bin"
     with WheelFile.open(wheel_candidates[0]) as source:
         install(
diff --git a/tests/functional/test_check.py b/tests/functional/test_check.py
index f50f5593e..c42e88bbe 100644
--- a/tests/functional/test_check.py
+++ b/tests/functional/test_check.py
@@ -10,10 +10,8 @@ from tests.lib import (
 def matches_expected_lines(string: str, expected_lines: Collection[str]) -> bool:
     # Ignore empty lines
     output_lines = list(filter(None, string.splitlines()))
-    # We'll match the last n lines, given n lines to match.
-    last_few_output_lines = output_lines[-len(expected_lines) :]
     # And order does not matter
-    return set(last_few_output_lines) == set(expected_lines)
+    return set(expected_lines).issubset(set(output_lines))
 
 
 def test_basic_check_clean(script: PipTestEnvironment) -> None:
diff --git a/tests/functional/test_freeze.py b/tests/functional/test_freeze.py
index 0a7cedd11..ea2fef37d 100644
--- a/tests/functional/test_freeze.py
+++ b/tests/functional/test_freeze.py
@@ -82,8 +82,8 @@ def test_basic_freeze(script: PipTestEnvironment) -> None:
     result = script.pip("freeze", expect_stderr=True)
     expected = textwrap.dedent(
         """\
-        ...simple==2.0
-        simple2==3.0...
+        ...simple==2.0...
+        ...simple2==3.0...
         <BLANKLINE>"""
     )
     _check_output(result.stdout, expected)
@@ -1016,7 +1016,7 @@ def test_freeze_skip_work_dir_pkg(script: PipTestEnvironment) -> None:
 
     # Freeze should not include package simple when run from package directory
     result = script.pip("freeze", cwd=pkg_path)
-    assert "simple" not in result.stdout
+    assert "\nsimple==" not in result.stdout
 
 
 def test_freeze_include_work_dir_pkg(script: PipTestEnvironment) -> None:
diff --git a/tests/functional/test_install_check.py b/tests/functional/test_install_check.py
index 8a8a7c93a..bbda083f7 100644
--- a/tests/functional/test_install_check.py
+++ b/tests/functional/test_install_check.py
@@ -57,6 +57,7 @@ def test_check_install_canonicalization(script: PipTestEnvironment) -> None:
     )
     assert "requires" not in result.stderr
     assert result.returncode == 0
+    return
 
     # Double check that all errors are resolved in the end
     result = script.pip("check")
diff --git a/tests/functional/test_list.py b/tests/functional/test_list.py
index e611fe7cb..c716f65c5 100644
--- a/tests/functional/test_list.py
+++ b/tests/functional/test_list.py
@@ -1,5 +1,6 @@
 import json
 import os
+import re
 from pathlib import Path
 
 import pytest
@@ -42,8 +43,8 @@ def test_basic_list(simple_script: PipTestEnvironment) -> None:
 
     """
     result = simple_script.pip("list")
-    assert "simple     1.0" in result.stdout, str(result)
-    assert "simple2    3.0" in result.stdout, str(result)
+    assert re.search(r"simple\s+1\.0", result.stdout), str(result)
+    assert re.search(r"simple2\s+3\.0", result.stdout), str(result)
 
 
 def test_verbose_flag(simple_script: PipTestEnvironment) -> None:
@@ -55,8 +56,8 @@ def test_verbose_flag(simple_script: PipTestEnvironment) -> None:
     assert "Version" in result.stdout, str(result)
     assert "Location" in result.stdout, str(result)
     assert "Installer" in result.stdout, str(result)
-    assert "simple     1.0" in result.stdout, str(result)
-    assert "simple2    3.0" in result.stdout, str(result)
+    assert re.search(r"simple\s+1\.0", result.stdout), str(result)
+    assert re.search(r"simple2\s+3\.0", result.stdout), str(result)
 
 
 def test_columns_flag(simple_script: PipTestEnvironment) -> None:
@@ -67,8 +68,8 @@ def test_columns_flag(simple_script: PipTestEnvironment) -> None:
     assert "Package" in result.stdout, str(result)
     assert "Version" in result.stdout, str(result)
     assert "simple (1.0)" not in result.stdout, str(result)
-    assert "simple     1.0" in result.stdout, str(result)
-    assert "simple2    3.0" in result.stdout, str(result)
+    assert re.search(r"simple\s+1\.0", result.stdout), str(result)
+    assert re.search(r"simple2\s+3\.0", result.stdout), str(result)
 
 
 def test_format_priority(simple_script: PipTestEnvironment) -> None:
@@ -80,16 +81,16 @@ def test_format_priority(simple_script: PipTestEnvironment) -> None:
     )
     assert "simple==1.0" in result.stdout, str(result)
     assert "simple2==3.0" in result.stdout, str(result)
-    assert "simple     1.0" not in result.stdout, str(result)
-    assert "simple2    3.0" not in result.stdout, str(result)
+    assert not re.search(r"simple\s+1\.0", result.stdout), str(result)
+    assert not re.search(r"simple2\s+3\.0", result.stdout), str(result)
 
     result = simple_script.pip("list", "--format=freeze", "--format=columns")
     assert "Package" in result.stdout, str(result)
     assert "Version" in result.stdout, str(result)
     assert "simple==1.0" not in result.stdout, str(result)
     assert "simple2==3.0" not in result.stdout, str(result)
-    assert "simple     1.0" in result.stdout, str(result)
-    assert "simple2    3.0" in result.stdout, str(result)
+    assert re.search(r"simple\s+1\.0", result.stdout), str(result)
+    assert re.search(r"simple2\s+3\.0", result.stdout), str(result)
 
 
 def test_local_flag(simple_script: PipTestEnvironment) -> None:
@@ -125,8 +126,8 @@ def test_multiple_exclude_and_normalization(
     assert "Normalizable_Name" in result.stdout
     assert "pip" in result.stdout
     result = script.pip("list", "--exclude", "normalizablE-namE", "--exclude", "pIp")
-    assert "Normalizable_Name" not in result.stdout
-    assert "pip" not in result.stdout
+    assert "Normalizable_Name " not in result.stdout
+    assert "pip " not in result.stdout
 
 
 @pytest.mark.network
diff --git a/tests/lib/venv.py b/tests/lib/venv.py
index fac54d3bd..6bfe3cfdc 100644
--- a/tests/lib/venv.py
+++ b/tests/lib/venv.py
@@ -9,6 +9,7 @@ import venv as _venv
 from pathlib import Path
 from typing import Dict, Literal, Optional, Union
 
+import pytest
 import virtualenv as _virtualenv
 
 VirtualEnvironmentType = Literal["virtualenv", "venv"]
@@ -35,7 +36,7 @@ class VirtualEnvironment:
             self._venv_type = venv_type
         else:
             self._venv_type = "virtualenv"
-        self._user_site_packages = False
+        self._user_site_packages = True
         self._template = template
         self._sitecustomize: Optional[str] = None
         self._update_paths()
@@ -234,6 +235,8 @@ class VirtualEnvironment:
 
     @user_site_packages.setter
     def user_site_packages(self, value: bool) -> None:
+        if not value:
+            pytest.skip("Gentoo: skipping due to lack of system site-packages")
         self._user_site_packages = value
         if self._legacy_virtualenv:
             marker = self.lib / "no-global-site-packages.txt"