Hi, I'm Robinson, and I’m happy to help you today.
Which is the "last run result" of the task? This information may have information on what is blocking the task to run.
Another option is to create a batch file to call your python script and set this batch file in the task scheduler. You can see more information at this link.
https://datatofish.com/python-script-windows-sc...
Note: This is a non-Microsoft website. The page appears to be providing accurate, safe information. Watch out for ads on the site that may advertise products frequently classified as a PUP (Potentially Unwanted Products).