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[bdjohns1]

I've recently been having a problem where MC doesn't recognize that it's already synced to my iPod, and insists it needs to delete and recopy everything.  Here's the chain of events:

1) Start with a fresh iPod (5G 30GB)
2) Make sure current FW is loaded via iTunes
3) Initialize in MC
4) Sync in MC
5) Use the iPod - combination of standalone, and with the harman/kardon drive+play system in my car
6a) Sometimes, I come back and it syncs fine. 
6b) Sometimes, I plug in, and it'll tell me that all of the files currently on the iPod (~3000) need to be deleted (if I have "delete files not in sync list" checked) or that the iPod will be over capacity (if unchecked)
7) I can go over to iTunes and interact with the iPod just fine, so the iTunesDB should be good (or else MC's filehandling isn't robust enough.

The workaround is just to initialize it again and reload, but I don't think that's acceptable at all - if I have to wait 40 minutes to re-sync my music, it's not worth it to use MC.  Next time it happens, I can provide an iTunesDB file if that'd be helpful.

[SwellGuy]

Did iTunes have the opportunity to rebuild the iPod database in the interim? There was a small change in build 120.0.181 that addressed a daylight savings time issue that could also cause this to happen once but after you re-sync it shouldn't happen again.

[bdjohns1]

Sorry to bump up an old post, but I've had this problem pop up again.  I still use iTunes for a handful of things (like syncing purchased video from iTMS, since MC can't/won't do that).  I recently upgraded to the most recent version of iTunes, and had the following issues:

1) About ~280 out of 3000+ songs were "lost" in MC12 - the files were physically present on the iPod and could be played, but MC couldn't see them and wanted to re-sync.  All songs were unprotected AAC files.
2) Videos (purchased from iTMS) are being lost - I have season 1 of The Office (6 episodes).  After loading them through iTunes and disconnecting, I see all 6.  After I went back to MC and re-sync'd, the list was down to 3.  Further, the titles aren't matching the videos - ie, I select "Diversity Day", and get "Health Care".  "Hot Girl" gets me "Basketball".  Clearly, MC is monkeying around with parts of the iTunesDB that it doesn't know how to work with properly.

Guess I'll have to reinitialize again.