Bruce Tognazzini, widely regarded as the father of the Macinosh user interface, has drawn up a list of what he regards as the The 10 Most Persistent Design Bugs.
1. Power failure Crash
If the computer loses power for more than a few thousandths of a second, it throws everything away.
2. The macintosh dock
There are actually nine separate and distinct design bugs in the Dock, probably a record for a single object. You can read about them all in my Article, The Top 9 Reasons the Dock Still Sucks
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3. Mysteriously dimmed menu items
Designers offer no way for users to discover why a given menu or option has been dimmed (grayed out), nor how to turn it back on.
4. ASCII sort
15 Dec 2008 sorts as being before 2 Jan 1900
5. URL naming bug
Many browsers disallow entry of spaces & other normal human-language characters into web addresses. The rest do inappropriate things with them.
6. Let's you save me some work
Weird formats for standardized data
7. The disk drive nazi
"Unauthorized" removal of floppy or hard disks is punished severely
8. ecommerce hostility
ecommerce sites are making it as difficult to buy products as humanly possible
9. "Smart" functions that aren't smart
"Smart" functions often make the wrong decisions
10. Focus-stealing
You're working on a multitasking system, typing away merrily in window A. Meanwhile, some background task decides it needs your attention, pops up a dialog, and moves the keyboard input focus from the window you were working on to its dialog box.