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.