Sometimes if I'm out of time, I'll get that pop-up to update an application and ignore it for a while if I'm otherwise busy. But sometimes I'm so excited for an update, like the iPhone's 2.0 update, that I'll go to great lengths to download it. In that case, I was so eager for the App Store that I manually applied it to my phone, rather than waiting for the official go-ahead, which would have been infinitely easier (and was a semi-waste since I bought the new iPhone the next day, but it was still worth it!).

Gizmodo's got a great list of historical firmware updates that turned out to be epic failures in many cases, and an explanation of why it never hurts to wait a few days to update. This is kind of why I haven't done the iPhone 2.0.1 firmware update yet (that, or laziness).
But as for you, I want to know: Do you always update when you get prompts or when you know they're available? Or do you wait, or sometimes — gasp! — never get the update?

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I usually do, unless I hear of a bug in the update.
1I usually wait with Itunes because I worry that my ipod won't sync to my last.fm page :/ Idk, it has happened before
2I think it's more laziness, or something of the sort, but I always put it off for awhile. Even if it doesn't involve me doing anything but clicking "Yes," if I'm doing something else and my computer wants me to shut down because of an update, I get super frustrated with it. How dare you ask me to shut down while I'm in the middle of something.....?like surfing www.geeksugar.com Ha! :]
3If it's a critical update, yes. It can wait if it's negligible.
4if i get a prompt, i'll update. sometimes i don't even notice what is different, haha yeah so..
5sometimes updates aren't better. ask the people who updated IE!
6i wait
7I don't update right away, because my iPod touch is jailbroken. *grin*
Only after I find a suitable way to jailbreak the newest firmware, I will get the update. Currently my iPod Touch has firmware 2.0.
Heard that 2.1 is a relatively minor update, so I'm not in a hurry for that one.
8It depends on if I have to restart my machine or not- or how bad I've been waiting for the update. Currently I think I would do immediate installs of any Leopard or iPhone updates... I can wait on Quicktime or Java.
9There was one time I didn't wait - and that was the iPhone 2.0 firmware update. My phone was a brick for 5 hours while the iTunes servers were down because I couldn't connect to reactivate. I waited until today for the 2.0.1 update, hahah.
10I always wait to upgrade software or firmware, especially on the iPhone. I wait for reports from other users first.
11my itunes updated itself the other day (it got tired of reminding me) and it messed up my whole library!! i have duplicates of files, 'missing' songs (they have the lil ! next to it)... messy messy... this is why i dont update
and i never update AIM
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