Some jpeg images won't sync to iPad

When I sync a folder to my iPad using iTunes some files don't copy. If I make a small edit to those files and re-file and then re-sync the file transfers OK. It's as is the file is corrupted in some way but I can open the files in all apps which handle jpegs and none report an error. The files are originally edited in CS6. It's only some files and the process to produce them is always the same. Any clues?

If you have very many images, make sure the missing files haven't copied already. Happened to me using the somewhat older My Photo Stream channel.
Needed to move about 80 pics from the iPad to the Mac. The first bunch, about 70, went thru flawlessly. Then in the last batch, there was one particular image that would just not sync on My Photo Stream, try as I might. Sure, it duped 3-4 times in the Camera Roll, but no dice. Only later did I discover that it had already synced at the very beginning and iOS was refusing to dupe it on the Stream, clever thing...

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