Sendmail

Raised as a usability problem by 5 people on Hacker News over 12 years (2014–2025), in 4 threads.

People raised many different problems with Sendmail, 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 5 complaints

M4-based configuration is a nightmare that was painful to work with for years2025-04-18
Setting up sendmail configuration is extremely hard and horrendous2022-11-08
Poorly designed config tools force time spent learning arbitrary, hard-to-use interfaces2016-05-24
Getting a correctly working mail server takes long, requiring reading every arcane option2014-09-16
Getting TLS to work with older Exchange servers is nearly impossible, with workarounds hard to find2014-09-16