Earler today, after 48h uptime and a few hours running in the background, an attempt to quit Microsoft Entourage generated this crafty riddle (disguised as a dialog box) requesting my immediate action:

WTF, or am I simply asking too much from my software?

What type of changes do you make that linger around until you finally decide / need to restart (which for us Mac Pro desktop users is about once a week excluding program installation(s)) whereby completely kill all running apps? After all, I wouldn’t want to lose any precious settings .. but the $1m question is WHICH ONES?

I’m a semi-normal Entourage / Exchange / GTD practitioner, and my application of choice is open almost 24/7. I use it a lot. Sometimes I even make changes. You know, small things - public folder access permissions, task list management, etc. But wait, don’t most changes either take effect immediately or force/ask a restart afterwords? I mean, when is the last time you changed the font size in Word / Pages / etc., it doesn’t immediately show up and you think ‘Oh gosh, I completely forgot, it’ll execute later .. my application keeps its own priority list.’? Uh, no.

Dear Entourage: If you’re so ninja-ly programmed to suspend the exit command, letting me know that I’m in danger of losing some changes, why not give me some clue as to which ones exactly are in jeopardy? Or even how about hinting at the age of the ‘original’ settings. Thanks.

What’s the most humorous error message you’ve come across lately?