diff --git a/src/poetry/utils/env/base_env.py b/src/poetry/utils/env/base_env.py
index 487a0aa2276..eb8dac6cf97 100644
--- a/src/poetry/utils/env/base_env.py
+++ b/src/poetry/utils/env/base_env.py
@@ -219,8 +219,11 @@ def platlib(self) -> Path:
 
         return self._platlib
 
+    def _get_lib_dirs(self) -> list[Path]:
+        return [self.purelib, self.platlib]
+
     def is_path_relative_to_lib(self, path: Path) -> bool:
-        for lib_path in [self.purelib, self.platlib]:
+        for lib_path in self._get_lib_dirs():
             with contextlib.suppress(ValueError):
                 path.relative_to(lib_path)
                 return True
diff --git a/src/poetry/utils/env/system_env.py b/src/poetry/utils/env/system_env.py
index 81ec7400d67..e088e684480 100644
--- a/src/poetry/utils/env/system_env.py
+++ b/src/poetry/utils/env/system_env.py
@@ -2,6 +2,7 @@
 
 import os
 import platform
+import site
 import sys
 import sysconfig
 
@@ -87,3 +88,6 @@ def get_pip_version(self) -> Version:
 
     def is_venv(self) -> bool:
         return self._path != self._base
+
+    def _get_lib_dirs(self) -> list[Path]:
+        return super()._get_lib_dirs() + [Path(d) for d in site.getsitepackages()]
diff --git a/tests/utils/test_env.py b/tests/utils/test_env.py
index 1ca5893e816..64258587a70 100644
--- a/tests/utils/test_env.py
+++ b/tests/utils/test_env.py
@@ -1,6 +1,7 @@
 from __future__ import annotations
 
 import os
+import site
 import subprocess
 import sys
 
@@ -1475,8 +1476,13 @@ def test_env_system_packages_are_relative_to_lib(
     venv_path = tmp_path / "venv"
     EnvManager(poetry).build_venv(path=venv_path, flags={"system-site-packages": True})
     env = VirtualEnv(venv_path)
-    pytest_dist = metadata.distribution("pytest")
-    assert env.is_path_relative_to_lib(pytest_dist._path)  # type: ignore[attr-defined]
+    site_dir = Path(site.getsitepackages()[-1])
+    dist = next(
+        p
+        for p in metadata.distributions()
+        if p._path.relative_to(site_dir) is not None  # type: ignore[attr-defined]
+    )
+    assert env.is_path_relative_to_lib(dist._path)  # type: ignore[attr-defined]
 
 
 @pytest.mark.parametrize(