Install Manager Does Not Work Over SSH

[DarkArc]

Install source and version

• Installed from the Windows Store
• Installed with the MSIX from python.org
• Installed with the MSI from python.org
• Installed with winget install 9NQ7512CXL7T

Version: 25.2

Describe the bug
Using Python over SSH that's installed with the Python Install Manager does not work unless the user is logged in.

To Reproduce
Steps to reproduce the behavior:

1. Install OpenSSH and the Python Install Manager on Windows Server
2. SSH into the user WITHOUT being graphically logged in
3. Attempt to launch Python in the shell

Expected behavior
Python's REPL launches.

Additional context
The error: "The system cannot execute the specified program." is printed.

[zooba]

Hmm, interesting. This is going to need setting up and testing, which may take some time for me to get to.

I suspect that OpenSSH isn't running in a native Windows shell (cmd/PowerShell) on the remote system - though I could be wrong - and whatever shell it's using doesn't support app execution aliases (e.g. Cygwin didn't support it until a couple years ago, and still has bugs, and most Bash shells for Windows are based on Cygwin's so they have the same bugs).

The easiest workaround should be to use the MSI installer for this case. But there may be something else going on, since I don't actually know how OpenSSH works.

[iBz-04]

did you choos the Install Python for 'all users' during installation , also you can also attempt to call the actual executable directly if you can locate its installation path in C:\Program Files\WindowsApps, though this is difficult due to permissions

[DarkArc]

I uninstalled the install manager from that server and went back to the old installers.

If I recall correctly, I think the issue has something to do with the mechanism requiring a graphical environment. I noticed a window being created briefly when running python through the install manager. That seemed to happen even when I ran python over SSH.

My presumption is that without the graphical environment it just doesn't operate properly (note if you are logged in to the graphical environment this DOES/did work). I don't know how fixable that is.

I'm not much of a Windows guy; this was largely a courtesy bug report. I unfortunately don't have time currently to try again and troubleshoot.

[zooba]

Okay, thanks for the notification. If I get a chance to set up a repro environment, I'll have a look, but if anyone else has one and has the time to try a few things, that'd be really helpful too.

[wrightsg]

+1

Ran into this trying to use Python install manager for a Jenkins build agent (running Windows Server 2025). In this use case, Jenkins runs a script that calls python via SSH which subsequently fails.

Need to revert to MSI installer for now...

I can reproduce the issue and run some tests if you want.

[zooba]

@wrightsg That would be really helpful. I think the main things I'd like to confirm are:

• how was the install manager installed?
• does it make a difference to install it with Add-AppxProvisionedPackage -Online -PackagePath python-manager-<version>.msix (and possibly reconnecting/rebooting after, though it shouldn't be necessary)
• assuming you set it up interactively and add the global commands directory to PATH, do those commands work? (typically %LocalAppData%\Python\bin, but you'll have to have installed a version first)