Album art not syncing to iPhone for playlists

A while ago I had a crash which wiped all the music synchronisation settings from my phone.

Until that point I'd synced based on selecting albums and artists in iTunes when the phone was plugged in, however having lost all that I decided it would be better to create playlists and sync those - that way if it happened again I just have to select half a dozen playlists to sync and I'm done.

The issue I have is that this doesn't seem to synchronise album art in most cases. The album art is there in iTunes but not on the phone.

If I select an artist to sync individually the artwork will appear (and will stay even when the artist selection is removed so it's just the playlist keeping the track on the phone), but without that it won't.

EDIT: Selecting the album individually doesn't seem to push the art work across so that may be a red herring. It's all feeling rather random.

Any thoughts on what I can do to force the artwork on to the phone without having to individually select every artist / album / track?

(iTunes 10.7 and iOS 6.0 on an iPhone 4S)

Solution 1:

Denis Ahrens mentioned something about that in the last episode of mobileMacs (timecode).

For those of you who don't know German: He said that all of his music is lossless and that iTunes recently learned how to encode these files to 256kbit/s AAC when syncing his music to his iPhone. When he switched this on, he experienced the same problem that you have: No cover art at all. He explained that some people seem to get the cover art and some don't.

If I understood him right (even for native speakers, he talks very fast and the context isn't always clear) he says that the parts of your library that get converted from lossless while transferring are missing the cover art while the tracks/albus/files that you convert explicitly before syncing get the cover art – but as I said, I'm not sure about that.

I have neither iOS 6 nor lossless music so I can't test this theory myself, I can only pass on what I heard; I hope it helps. (By the way, Denis concludes that he hasn't found a workaround yet and advises to wait for the fix.)