I am not sure what to make of this but I am testing on an iPad and the auto update does not seem to work properly. When I start the script it tells me there is a new version and asks whether I want to update. I say yes and it comes back and says the update was done and to restart the program and I restart it as I do on my other devices. However the update does not seem to take and it goes through the same cycle again. This happened with the previous release and I thought that I would just do a manual update to 1.20 but it is now happening again with 1.21. It’s obviously not a big deal as I can always do the manual update but I thought I would mention it.
Is your outline.py local or on iCloud, I got tHe same problem, only once, but my script is on iCloud and download from GitHub to iCloud was done but perhaps not yet to your local device.
If your script is in your local Pythonista, was it edited in a Pythonista tab or run from a shortcut?
When you restart, do you remove Pythonista from memory first? If no, not sure Pythonista does not have a cache.
It is always better to remove it from memory because if the script changes in some created ObjectiveC classes, they are not replaced without restarting Pythonista it-self.
Are you waiting some time before to restart?