TrueCrypt

Raised as a usability problem by 4 people on Hacker News over 7 years (2010–2016), in 4 threads.

People raised many different problems with TrueCrypt, 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

Containers above 50 MB are unusable for cloud storage2016-12-13
Creates multiple conflicting volume copies that must be merged by hand2011-04-16
UI is horrid and overly complicated for a simple setup2010-09-12
Interface is cumbersome and counter-intuitive, requiring repeated password typing and risking data loss2010-07-20