https://bugs.winehq.org/show_bug.cgi?id=50471
--- Comment #4 from Alan aversa@email.arizona.edu --- (In reply to ameniutaeba1978 from comment #0)
So the problem is on wine 5.22 or later
I get the same issue with Wine 5.21 (using an old, backed-up prefix). In this case it does prompt me to upgrade to Kindle 1.30, but when I try, the download hangs (as if network connectivity gets cut off at a certain point). I'm wondering if it's really the Amazon server that's causing issues.