This was a mystery.

I had been messing with my photo sync settings in iTunes, so that I could get more photos onto my iPhone. I started getting this iTunes sync error, -256. I googled for this but naturally Google ignored "256", as it seems to enjoy ignoring the most important words in my queries. I couldn't find an answer, and I had no luck deleting and resyncing photos. I decided I should wipe the phone and restore from backup at some point, but "not today".

A few weeks later (today) I discovered the real culprit. At some point in the past few months I had accidentally deleted podcast files in iTunes. I had restored the iTunes catalog file, and I had restored the files themselves from Trash. Or so I thought. I discovered today that I hadn't gotten them all. Once I fixed that (by deleting in iTunes and telling it to download them again), the photo sync worked again!

Grr1: iTunes does too many things, and it's hard to diagnose errors. Grr2: "error -256" is unhelpful. If it told me what it was doing at the time, it would've helped me realize it was podcasts and not photos that were the problem. Grr3: iTunes catalog and the files on disk can get out of sync; this is fragile.

I'm writing this blog post so that if anyone else has error -256, and convinces Google not to ignore that term, they might find a solution here.

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