Oh, you're gonna REALLY love this one.

iPhoto works well for the generalized task of arranging some albums for going onto the iPod. I could drag the desired photos from my file share into iPhoto on the Mac, and they all showed up correctly, with iPhoto correctly interpreting the EXIF data and every single photo appeared in its correct orientation.

As you said, it leaves the source photos and folders clean, making its own database on the mac. Great, so far so good. I'm thinking this is going to be a good solution.

So I did this for several of my photo folders, a total of 345 pictures. Then went into iTunes on the Mac and hit "sync" and off it went. Cruised along, synched all the photos, then I look at the photos on the iPod and........

They are random. Only about half of the portrait photos are in proper orientation. The other half are sideways as I illustrated earlier in this thread.

Hm. Perhaps it's just as I feared and it's not interpreting the EXIF data at all, and the ones that are coming up correctly are ones that I'd somehow managed to pre-process and I don't remember doing it.

So I find some adjacent photos on the iPod, where some of them are in the correct orientation and the others are in the wrong orientation. And I look at the files back at the source on the PC.

*NONE* of the photos were preprocessed. All of them are identical, all of them were untouched original source photos. The EXIF "orientation" field is the same for all of them.

Just to prove it, I am attaching a ZIP file of two of the photos. On the iPod, one of these photos displays in the correct orientation, the other displays sideways. 484 displays correctly, 496 displays sideways.

Note that both of the photos display correctly in iPhoto on the Mac.

Also note that it's not an intermittency problem with the orientation sensor in the iPod; The photos that are wrong on the iPod are *ALWAYS* wrong, and the photos that are right on the iPod are *ALWAYS* right. I can spin and twist the iPod every which way and it does all the expected rotations of the images. It's just that the "bad" ones are always in exactly the wrong orientation, exactly as if the EXIF data had been ignored.

Can anyone see a difference in the two files zipped up here that might cause them to be interpreted differently by iPhoto/iTunes?