Whats the tool that you have to use but dislike the most? Why?
I felt this would be a great Q&A to identify some bad tools. To start with, really have been disliking hipchat a lot. Have to use it as a company stickiness to Altassian.
Stamps.com is equally bad. SCAN form reprint doesn't work, crashes randomly on return from sleep, sets the Windows default printer to whatever thermal printer it's using at the time, has the most braindead address correction algorithm I've ever seen. (For one, it doesn't like state names that are two words!) Also they haven't updated the 13oz -> 16oz cutoff for first class mail on return labels yet.
Madcap Flare is also some pretty miserable enterprise-ware.
Magento is also bad, of course, but that's universally hated, no surprise there.
Problem, it's arguably the best of the bunch which just shows how bad things are.