You shouldn't beat yourself up too much. TLS is HARD and poorly documented, and implementations vary significantly between applications and vendors (and are ver

You shouldn't beat yourself up too much. TLS is HARD and poorly documented, and implementations vary significantly between applications and vendors (and are very dumbly designed). TLS is what you get when you let someone implement technology with specific domain knowledge (encryption) but no UX abilities or a comprehensive understanding of how their solution will be used. I had the same horrified realization a few years ago when someone explained Certificate Transparency[1] to me. [1] https://en.wikipedia.org/wiki/Certificate_Transparency https://en.wikipedia.org/wiki/Certificate_Transparency