My 2 cents

I know, The Daily WTF does a great job at doing this, but I really liked these error messages I was presented with recently.
Writely showed me this very funny pop-up dialog box:

Windows Movie Maker annoyed me with this one:

I'll make mine the words of Alan Cooper on About Face 2.0:

Considerate software is conscientious
If we rely on a word processor to draft a new MicroBlitz Contract and then try to [save it in the same folder as an existing, but older, MicroBlitz Contract], the program offers the choice of either overwriting and destroying the old contract or not saving it at all. The program not only isn't as capable as [a human assistant who saw
the name conflict and appropriately renamed the contracts], it isn't even as capable as [a human assistant who put the two contracts in the same folder]. It is stupider than a complete idiot. The software is dumb enough to make an assumption that because they have the same name, I meant to throw the old one away.

And my own 2 cents on WMM's error message:

1. If there is such a thing as an invalid filename, tell me before hand what my valid options are. Don't wait until I use "invalid" options to let me know I've used them, right? It is worth mentioning that even after the input validation I was not told what those invalid names were. This inconsiderate application seems to want me to keep trying until I get it right.


2. What happened to the option to overwrite an existing file, asking for my consent? That was actually what I wanted to do but was forced instead to save the file with a bogus name, delete previous one manually, and then rename bogus-named one with the intended name. There seems to be total lack of attention to detail and lazy programming here.