OTR

Raised as a usability problem by 8 people on Hacker News over 10 years (2013–2022), in 8 threads.

People raised many different problems with OTR, 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 8 complaints

Requires installing plugins, non-standard clients, and manual setup by everyone in the chat2022-10-22
Off-the-record messaging is so hard to use that almost nobody bothers with it2020-10-19
Described as an old hack that is not really usable2019-04-07
Initiating an OTR session requires the friend to physically tap a notification2016-07-24
Breaks in many places and has obvious bad user experience2015-03-29
OTR implementations are more painful to use than PGP/GPG2013-07-15
Users choose guessable secrets or send them over insecure channels to verify contacts2013-07-10
Author hasn't found a user-friendly way to handle the UI/UX problem of differing instances across devices2013-06-15