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I want to losslessly rotate all JPEGs that have been shot in portrait mode and remove the rotate flag, so iPhoto doesn't stops rotating them. Any easy way to do that?

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up vote 2 down vote accepted

Found it:

jhead -autorot <filename> does it. To rotate all the files in a directory, just do jhead -autorot *.

You must have both jhead and jpegtran installed. jhead can be found here (OSX binary available). jpegtran can be found here (download the source and compile it using ./configure && sudo make all install).

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To clarify, running jhead -autorot * will rotate only the files in portrait mode (which is usually what is needed). – this.lau_ May 7 '14 at 1:01

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