I had a few read-only files on my hard drive, that I had included in my auto-sync list.
I changed the genre tag for some of these files, and synchronized the tags. At that time MM asked whether I wanted to remove the read-only attibute in order to apply the tag change, and I clicked yes.
On the subsequent synchronization, MM attempted to copy them again (as expected). But it failed with with a vague message ("could not copy... ignore/retry/cancel"). After investgating, it looks like MM is copying the read-only attribute at the initial sync operation, but on any subsequent copy it doesn't detect that the file is read-only and cannot replace it. If I manually remove the read-only attribute on the iPod, the problem is fixed.
So I'd suggest to either not copy the read-only attribute to the iPod, or handle this situation with a better message (such as "the file is read-only, would you like to remove the read-only attribute").
Files with read-only attribute and iPod sync
Moderator: Gurus