Enigmail

Raised as a usability problem by 4 people on Hacker News over 11 years (2013–2023), in 4 threads.

People raised many different problems with Enigmail, but no single problem has yet been raised by 3 people in 3 different months and threads.

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 4 complaints

GPG email encryption not intuitive for the average person to use2023-09-12
Keeping certificates set up on each new system needs lots of googling2016-02-01
Interface for setting per-user default encryption is confusing2013-07-28
Has to fiddle with multiple settings to get encrypted mail sending working2013-07-08