Dennis, Eryk, Thank you for your responses. The results for assoc and ftype are the same on my machine (should be tested on person C's pc, too).
The space in filepath was one of my first guesses, but unfortunately I was not able to reproduce the error by putting a space in the filepath. But as Eryk you pointed out, there must be a file with a matching filename in order to get an error. This would explain why it is not reproducible. Here are some of my test results: Used test code =========== from pathlib import Path import win32process # from pywin32 (h_process, _, dw_process_id, _) = win32process.CreateProcess( None, # module name r"C:\tmp\first second\some.exe" , None, # Process handle not inheritable. None, # Thread handle not inheritable. 0, # Set handle inheritance to FALSE. 0, # Creation flags. None, # Use parent's environment block. None, # If None - use parent's starting directory. win32process.STARTUPINFO(), ) # STARTUPINFO structure. Test 1 ====== - Create broken exe with notepad (empty file) - Broken exe at: C:\tmp\first.exe (or C:\tmp\first without .exe) - Working exe at C\tmp\first second\some.exe -> The broken exe is found first: Traceback (most recent call last): File ".\testfix.py", line 5, in <module> (h_process, _, dw_process_id, _) = win32process.CreateProcess( pywintypes.error: (193, 'CreateProcess', '%1 is not a valid Win32 application.') Test 2 ===== - Same as Test 1, but use quoted string as the lpCommandLine (r'"C:\tmp\first second\some.exe"') -> The C\tmp\first second\some.exe starts without problems. So the problem might be that on the Person C's computer, there is actually a file called "first" that is creating the error. The reason why I was using win32process.CreateProcess like this was that I'm actually using pywinauto, which uses win32process.CreateProcess. I'll have to still test this, but apparently this will fix some possible bugs. Thank you! - Niko
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