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I would like to be able to plug in my portable HDD, and run some small app or script that would backup a certain set of files (itunes media and some documents) to a certain set of files

I need something that does transparent backups, no encryption or whatnot
It should also be smart enough to only backup changed or new files, and I would prefer it to not delete files that have been removed from the computer.

I had a nice rsync script that was working in Debian, but alas, I'm back to Windows for now.

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up vote 0 down vote accepted

Free version of SyncBack does this for you. Otherwise, DeltaCopy as fideli suggested.

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If you're familiar with rsync, have you looked at DeltaCopy? They also have a more user-friendly program called Syncrify if you prefer that.

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