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So I went with the first option and resized the ext3fs partition (sdb1) of which Ubuntu is installed and successfully cloned it to the smaller hard drive using partimage (though I haven't tried to boot from the new smaller drive yet; I've done everything remotely so far, so I'm not in front of the actual computer). Do I have to worry about the Extended (sdb2) and linux-swap partitions (sdb3) in terms of cloning or was creating those partitions with gparted enough?
I really (I mean *really*) don't like imaging like that - better to set up target partitions and use a filesystem copy (cp, rsync, ...).
You should be fine with the swap - although with Ubuntu (using UUID) you'll probably need to fix the fstab entry.
booya! worked sorta like magic. had to re-install grub using Live disc (I got a grub error 2), but after I rebooted everything came up and I'm back to normal with a new drive. got my first Linux cloning experience under my belt, feels good. partimage is a gawd send
how do I know for sure I *need* to fix the fstab entry for swap?
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