[sbierwagen]

UPS Worldship. Dog slow, (you sit there and watch it redraw each form multiple times) confirms on exit, and will refuse to exit if it's talking to the server, since its programmers had never heard of background tasks.

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.