Products · Product
S/MIME
Raised as a usability problem by 8 people on Hacker News over 13 years (2013–2025), in 8 threads.
No issue was raised by at least 3 people in 3 threads this year.
No issue was raised by at least 3 people in 3 threads in the last 5 years.
Every issue, all time, most people first
Encrypting extra headers is unsupported, and downgrade mode is hostileUnreviewed
20132026- Email users can't figure out certificates, so they bypass encryption2025-06-26
- Encrypting extra email headers is unsupported by clients and its downgrade mode is UX-hostile2019-07-19
- Mail encryption is still a PITA to use, especially on Android where Google lacks S/MIME support2014-08-13
S/MIME setup is complicated and hard to walk non-experts throughUnreviewed
20132026- S/MIME is practically unusable by ordinary people2025-03-28
- Installing and using S/MIME certificates requires obscure, multi-step format conversions and extensions2019-03-13
- S/MIME signing and encryption setup is heinously complicated, hard to walk non-experts through2013-08-20
Unreviewed issues were grouped by machine: Claude Haiku labelled each comment as a usability complaint, named what it's about and summed up the problem in a line, and a small model grouped similar problems. Nobody has checked them by hand. Expect mistakes.
The newest 9 complaints
- No one could design a user-friendly interface for the encryption system2025-10-03
- Email users can't figure out certificates, so they bypass encryption2025-06-26
- S/MIME is practically unusable by ordinary people2025-03-28
- Getting and loading a certificate is hard, requiring paid vendors and failing across tools2020-09-18
- Encrypting extra email headers is unsupported by clients and its downgrade mode is UX-hostile2019-07-19
- Recipients' systems mark signed emails as spam2019-03-13
- Installing and using S/MIME certificates requires obscure, multi-step format conversions and extensions2019-03-13
- Mail encryption is still a PITA to use, especially on Android where Google lacks S/MIME support2014-08-13
- S/MIME signing and encryption setup is heinously complicated, hard to walk non-experts through2013-08-20