iPhone software updates

It will tell you when there is an update and you have the option to download, download and install, or not.

It is also a good option to make sure you have Apple Updater running to tell you when a new iTunes is available, while not always, most times there is a new iTunes as well at the same time (as some features added to phone require changes to iTunes as well). So always best to have iTunes as up to date as possbible.

Message was edited by: DaVBMan

iTunes automatically checks for available updates when your iPhone is connected.

With your iPhone connected, check under the Summary tab for your iPhone sync preferences.

To the left of Check for Update, is when iTunes will automatically check for an available update for your iPhone. I believe the automatic check is every week, but updates are not provided weekly, or even monthly - at least not over the last year, so every week is plenty. Or you can manually select Check for Update at any time.

I have a question in the same vein.

I haven't updated since 1.1. Can I expect to encounter problems jumping up to the newest update?

You should not have any problems skipping updates to get the latest. There are occasional problems actually installing the update, especially if you do not have USB 2 ports or you are using a USB hub. Thee are workarounds, but they aren't pretty.