I'm not a stellarmate developer, but i know this way of upgrading debian based distributions since many years now. It just works best.
For myself, i would assume that the dialog box (application) was made for the desktop user's experience.
However, it is not very verbose about what's going on, so best use the "old way" to check for more output.

And yes, bugs are daily business in software development, it's just that the projects became way bigger and more complicated to maintain.
I wouldn't assume a room filling bug-hunting and functional testing team is at work for $50 of cost for a lifetime license.

It's bad when we run into bugs, even less severe. Sometimes there is an instant workaround available or made obvious.
I could not imagine doing Astrophotography without stellarmate again, but the Asiair stuff has features that don't work as well as with stellarmate, and for sure, it has and will have bugs too. Code is still written by humans...

Also try to look for existing forum threads covering stellarmate OS upgrade issues, might help.

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