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My MacBook just died and I brought it into the store to get it fixed. Luckily I have a recent backup (from last week) that I made with SuperDuper so I can actually plug it into my wife's Mac and boot it up -- the drive is a bootable clone -- and continue my work. Since I made the backup of course there were changes that I made to files, most of which were uploaded to Dropbox. When I boot up the external HD, what will Dropbox do? Will it automatically update the files to the most recent version?

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Yes. Dropbox uses the modification dates of files (among other items) to determine the most recent version. Once you restore your drive and enable Dropbox, it should replace your local files with more recent versions it has available.

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