python
@@ -254,6 +254,11 @@ pdb
   identified and executed.
   (Contributed by Tian Gao in :gh:`108464`.)
 
+* ``sys.path[0]`` will no longer be replaced by the directory of the script
+  being debugged when ``sys.flags.safe_path`` is set (via the :option:`-P`
+  command line option or :envvar:`PYTHONSAFEPATH` environment variable).
+  (Contributed by Tian Gao and Christian Walther in :gh:`111762`.)
+
 sqlite3
 -------
 

@@ -142,8 +142,10 @@ def check(self):
             print('Error:', self.orig, 'is a directory')
             sys.exit(1)
 
-        # Replace pdb's dir with script's dir in front of module search path.
-        sys.path[0] = os.path.dirname(self)
+        # If safe_path(-P) is not set, sys.path[0] is the directory
+        # of pdb, and we should replace it with the directory of the script
+        if not sys.flags.safe_path:
+            sys.path[0] = os.path.dirname(self)
 
     @property
     def filename(self):

@@ -2493,15 +2493,21 @@ def tearDown(self):
 
     @unittest.skipIf(sys.flags.safe_path,
                      'PYTHONSAFEPATH changes default sys.path')
-    def _run_pdb(self, pdb_args, commands, expected_returncode=0):
+    def _run_pdb(self, pdb_args, commands,
+                 expected_returncode=0,
+                 extra_env=None):
         self.addCleanup(os_helper.rmtree, '__pycache__')
         cmd = [sys.executable, '-m', 'pdb'] + pdb_args
+        if extra_env is not None:
+            env = os.environ | extra_env
+        else:
+            env = os.environ
         with subprocess.Popen(
                 cmd,
                 stdout=subprocess.PIPE,
                 stdin=subprocess.PIPE,
                 stderr=subprocess.STDOUT,
-                env = {**os.environ, 'PYTHONIOENCODING': 'utf-8'}
+                env = {**env, 'PYTHONIOENCODING': 'utf-8'}
         ) as proc:
             stdout, stderr = proc.communicate(str.encode(commands))
         stdout = stdout and bytes.decode(stdout)
@@ -2513,13 +2519,15 @@ def _run_pdb(self, pdb_args, commands, expected_returncode=0):
         )
         return stdout, stderr
 
-    def run_pdb_script(self, script, commands, expected_returncode=0):
+    def run_pdb_script(self, script, commands,
+                       expected_returncode=0,
+                       extra_env=None):
         """Run 'script' lines with pdb and the pdb 'commands'."""
         filename = 'main.py'
         with open(filename, 'w') as f:
             f.write(textwrap.dedent(script))
         self.addCleanup(os_helper.unlink, filename)
-        return self._run_pdb([filename], commands, expected_returncode)
+        return self._run_pdb([filename], commands, expected_returncode, extra_env)
 
     def run_pdb_module(self, script, commands):
         """Runs the script code as part of a module"""
@@ -3104,6 +3112,23 @@ def test_issue42384_symlink(self):
 
             self.assertEqual(stdout.split('\n')[2].rstrip('\r'), expected)
 
+    def test_safe_path(self):
+        """ With safe_path set, pdb should not mangle sys.path[0]"""
+
+        script = textwrap.dedent("""
+            import sys
+            import random
+            print('sys.path[0] is', sys.path[0])
+        """)
+        commands = 'c\n'
+
+
+        with os_helper.temp_cwd() as cwd:
+            stdout, _ = self.run_pdb_script(script, commands, extra_env={'PYTHONSAFEPATH': '1'})
+
+            unexpected = f'sys.path[0] is {os.path.realpath(cwd)}'
+            self.assertNotIn(unexpected, stdout)
+
     def test_issue42383(self):
         with os_helper.temp_cwd() as cwd:
             with open('foo.py', 'w') as f:

diff --git a/Misc/NEWS.d/next/Library/2023-11-05-20-09-27.gh-issue-99367.HLaWKo.rst b/Misc/NEWS.d/next/Library/2023-11-05-20-09-27.gh-issue-99367.HLaWKo.rst
@@ -0,0 +1 @@
+Do not mangle ``sys.path[0]`` in :mod:`pdb` if safe_path is set
Original file line number	Diff line number	Diff line change
		@@ -0,0 +1 @@
		Do not mangle ``sys.path[0]`` in :mod:`pdb` if safe_path is set