IIS

Raised as a usability problem by 15 people on Hacker News over 14 years (2009–2022), in 15 threads.

People raised many different problems with IIS, 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 15 complaints

Deploying a .NET app required tinkering with hidden settings and an unexplained app pool failure2022-03-13
Finds IIS extremely frustrating to use compared to Nginx2021-12-23
Configuring through menus and ticking boxes is complex and slow2018-08-30
Googling fixes then figuring out how options were translated is painful2016-12-13
App pool recycles after idle, taking everything down; many settings easily misconfigured2015-11-19
Configuring IIS as a reverse proxy requires many manual steps, clicking through GUI docs and editing buried files2015-04-09
Configuring failover and interceptor pattern together in IIS is frustrating2014-05-15
Must dig through 20+ screens and scattered config files to find values2013-12-17
Deleting one site instance breaks the others sharing the wildcard certificate, forcing rebuilds from scratch2013-08-01
MIME type option buried across many dialogs, taking far longer than a text-file edit2013-03-10
Hard-coded limits block non-CRUD apps, and removing them is poorly documented2011-12-29
Setting up PHP with MySQL on IIS needed many hoops, and not everything worked by default2011-11-08
Creating virtual servers needs right-clicking, form-filling and manual copying of settings, slower than scripting2011-08-31
Moving site configurations between servers is error-prone, and SSL sites break in transfer scripts2010-09-07
Can't remember which of 14 tabs holds needed setting2009-12-14