I had a similar experience a few months ago - A fresh debian and then stuff needed to run the Matrix/Synapse stuff - then went to do some addons and they balked

I had a similar experience a few months ago - A fresh debian and then stuff needed to run the Matrix/Synapse stuff - then went to do some addons and they balked at one installed thing not having the proper ssl stuff - which led into a rabbit hole of error messages and python stuff with very few search results.. only solution I could find that actually worked was someone posting a thing saying to downgrade the TLS to lower version.. Figured that might fix the main problem at the time, but then create new problems for other things. So I gave up. Will likely do a new box and new install with a different domain name to see if I can get it all working proper with modern tls/ssl stuff (think i saw something about a recent debian update doing some things with ssl and tls) - But no one got back to me on exporting user data from Synapse - of which I really just need usernames, email addys to a fresh install - so I gave up on that too.