pallets / pallets/click

`click.edit` on Windows throws WinError 14001 or 87

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Description

I found this bug while testing my own Click application. In about half the times click.edit() is attempted on Windows, notepad.exe will fail to launch with one of these two error messages (output under spoilers):

OSError: [WinError 87] The parameter is incorrect
PS C:\Users\Emory> python .\click-notepad-me.py
Traceback (most recent call last):
  File "C:\Users\Emory\AppData\Local\Python\pythoncore-3.14-64\Lib\site-packages\click\_termui_impl.py", line 729, in edit_files
    c = subprocess.Popen(
        args=shlex.split(editor) + list(filenames),
        env=environ,
    )
  File "C:\Users\Emory\AppData\Local\Python\pythoncore-3.14-64\Lib\subprocess.py", line 1038, in __init__
    self._execute_child(args, executable, preexec_fn, close_fds,
    ~~~~~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
                        pass_fds, cwd, env,
                        ^^^^^^^^^^^^^^^^^^^
    ...<5 lines>...
                        gid, gids, uid, umask,
                        ^^^^^^^^^^^^^^^^^^^^^^
                        start_new_session, process_group)
                        ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "C:\Users\Emory\AppData\Local\Python\pythoncore-3.14-64\Lib\subprocess.py", line 1552, in _execute_child
    hp, ht, pid, tid = _winapi.CreateProcess(executable, args,
                       ~~~~~~~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^
                             # no special security
                             ^^^^^^^^^^^^^^^^^^^^^
    ...<4 lines>...
                             cwd,
                             ^^^^
                             startupinfo)
                             ^^^^^^^^^^^^
OSError: [WinError 87] The parameter is incorrect

The above exception was the direct cause of the following exception:

Traceback (most recent call last):
  File "C:\Users\Emory\click-notepad-me.py", line 3, in <module>
    _ = click.edit()
  File "C:\Users\Emory\AppData\Local\Python\pythoncore-3.14-64\Lib\site-packages\click\termui.py", line 904, in edit
    return ed.edit(text)
           ~~~~~~~^^^^^^
  File "C:\Users\Emory\AppData\Local\Python\pythoncore-3.14-64\Lib\site-packages\click\_termui_impl.py", line 783, in edit
    self.edit_files((name,))
    ~~~~~~~~~~~~~~~^^^^^^^^^
  File "C:\Users\Emory\AppData\Local\Python\pythoncore-3.14-64\Lib\site-packages\click\_termui_impl.py", line 739, in edit_files
    raise ClickException(
        _("{editor}: Editing failed: {e}").format(editor=editor, e=e)
    ) from e
click.exceptions.ClickException: notepad: Editing failed: [WinError 87] The parameter is incorrect

or

OSError: [WinError 14001] The application has failed to start because its side-by-side configuration is incorrect. Please see the application event log or use the command-line sxstrace.exe tool for more detail
PS C:\Users\Emory> python .\click-notepad-me.py
Traceback (most recent call last):
  File "C:\Users\Emory\AppData\Local\Python\pythoncore-3.14-64\Lib\site-packages\click\_termui_impl.py", line 729, in edit_files
    c = subprocess.Popen(
        args=shlex.split(editor) + list(filenames),
        env=environ,
    )
  File "C:\Users\Emory\AppData\Local\Python\pythoncore-3.14-64\Lib\subprocess.py", line 1038, in __init__
    self._execute_child(args, executable, preexec_fn, close_fds,
    ~~~~~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
                        pass_fds, cwd, env,
                        ^^^^^^^^^^^^^^^^^^^
    ...<5 lines>...
                        gid, gids, uid, umask,
                        ^^^^^^^^^^^^^^^^^^^^^^
                        start_new_session, process_group)
                        ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "C:\Users\Emory\AppData\Local\Python\pythoncore-3.14-64\Lib\subprocess.py", line 1552, in _execute_child
    hp, ht, pid, tid = _winapi.CreateProcess(executable, args,
                       ~~~~~~~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^
                             # no special security
                             ^^^^^^^^^^^^^^^^^^^^^
    ...<4 lines>...
                             cwd,
                             ^^^^
                             startupinfo)
                             ^^^^^^^^^^^^
OSError: [WinError 14001] The application has failed to start because its side-by-side configuration is incorrect. Please see the application event log or use the command-line sxstrace.exe tool for more detail

The above exception was the direct cause of the following exception:

Traceback (most recent call last):
  File "C:\Users\Emory\click-notepad-me.py", line 3, in <module>
    _ = click.edit()
  File "C:\Users\Emory\AppData\Local\Python\pythoncore-3.14-64\Lib\site-packages\click\termui.py", line 904, in edit
    return ed.edit(text)
           ~~~~~~~^^^^^^
  File "C:\Users\Emory\AppData\Local\Python\pythoncore-3.14-64\Lib\site-packages\click\_termui_impl.py", line 783, in edit
    self.edit_files((name,))
    ~~~~~~~~~~~~~~~^^^^^^^^^
  File "C:\Users\Emory\AppData\Local\Python\pythoncore-3.14-64\Lib\site-packages\click\_termui_impl.py", line 739, in edit_files
    raise ClickException(
        _("{editor}: Editing failed: {e}").format(editor=editor, e=e)
    ) from e
click.exceptions.ClickException: notepad: Editing failed: [WinError 14001] The application has failed to start because its side-by-side configuration is incorrect. Please see the application event log or use the command-line sxstrace.exe tool for more detail

To replicate, run this script until you get one of these:

import click
_ = click.edit()
print("If you got here, no crash occurred")

Environment:

  • Python version: 3.12.14 / also reproduced on my system 3.14 install
  • Click version: 8.5.0
  • OS: Windows 11 (64-bit)

Contributor guide

Open the contributing guide

First steps

  1. Read the whole issue, then the project's contributing guide.
  2. Comment on the issue to say you are picking it up — it saves two people doing the same work.
  3. Fork the repository and make your change on a branch.
  4. Open a pull request that references the issue number.

Research direction

Start with click/_termui_impl.py, especially edit_files, and reproduce the failure by repeatedly running the provided click.edit() script on Windows. Trace how the editor command is passed to subprocess.Popen; done means click.edit() reliably launches notepad.exe without WinError 87 or 14001.

Written by the indexing model from the issue text.

Assessment

Tech stack
python
Domain
cli, operating-systems
Issue type
Bug
Difficulty
3/5
Estimated time
1-2 days
Activity status
Active
Clarity
Mostly clear
Newbie friendliness
68/100

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