Check whether pip module exists in shared lib before performing any actions

CHANGELOG.md

@@ -1,5 +1,6 @@
 ## dev
 
+- Use virtual environment's Python to check for pip's availability during reinstalling process
 - Drop support for Python 3.7
 - Make usage message in `pipx run` show `package_or_url`, so extra will be printed out as well
 - Add `--force-reinstall` to pip arguments when `--force` was passed

src/pipx/commands/reinstall.py

@@ -1,4 +1,3 @@
-import importlib.util
 import sys
 from pathlib import Path
 from typing import List, Sequence
@@ -47,12 +46,6 @@ def reinstall(
     else:
         package_or_url = venv.main_package_name
 
-    if importlib.util.find_spec("pip") is None:
-        raise PipxError(
-            f"Can not find pip. You may encounter issues uninstalling packages. "
-            f"Remove {PIPX_SHARED_LIBS} and run 'pipx reinstall-all' to fix them."
-        )
-
     uninstall(venv_dir, local_bin_dir, verbose)
 
     # in case legacy original dir name

src/pipx/shared_libs.py

@@ -53,7 +53,17 @@ def create(self, verbose: bool = False) -> None:
 
     @property
     def is_valid(self) -> bool:
-        return self.python_path.is_file() and self.pip_path.is_file()
+        if self.python_path.is_file():
+            check_pip = "import importlib.util; print(importlib.util.find_spec('pip'))"
+            out = run_subprocess(
+                [self.python_path, "-c", check_pip],
+                capture_stderr=False,
+                log_cmd_str="<checking pip's availability>",
+            ).stdout.strip()
+
+            return self.pip_path.is_file() and out != "None"
+        else:
+            return False
 
     @property
     def needs_upgrade(self) -> bool: