So I think I have found the underlying problem, which is not something a user can fix
Since allowing unsafe connections seems to solve the issue universally, it must have to do something with encryption
I just came across an article about a large amount of Let’s Encrypt certificates expiring on the 30th of September, which has troubled a lot of companies
And Let’s Encrypt just so happens to be the supplier of certificates for Plex as well
Still, it is weird that some files do work on a safe connection, and some don’t, but my guess is that the issue is caused by the expired Let’s Encrypt certificates
So let’s hope Plex manages to fix that issue soon
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