I was wondering if anybody has had any luck fixing songs with the Error status. I know the advice about simply doing Update iTunes Match, and that did help resolve a couple of errors for me, but my library is completely up now and I still have a group of about 300 songs showing Error as their status. It appears that there is actually something wrong with these song files--or at least something that iTunes as a whole (not just iCloud) doesn't like. I'd heard the advice that when something wasn't matching properly you should try converting it to AAC in iTunes. When I try this for any of the songs marked Error, I get the following message: Error occurred while converting the file " ". An unknown error occurred (-50). Sometimes iTunes runs almost the whole way through the conversion process before throwing the error; sometimes it throws it as soon as I tell it to create an AAC. But either way, it won't convert the Error files, to AAC or to other formats I've tried. The musical data in the files seems to be intact; spot testing suggests that they all play fine. But there's something about the files that iTunes refuses to handle, either to convert or to match with iCloud. Unfortunately I can't simply re-rip all these songs, because I don't have access to all the originals anymore (a couple of CDs are missing, one is badly damaged). Besides, these songs come from a variety of albums (often only 1 or 2 per album), so it would take forever to rip them all again. I'm hoping someone has encountered this conversion error before or has some thoughts on what I can do to make iTunes willing to work with them. I'm convinced if I can just correct whatever's bothering iTunes all the files will match in a heartbeat.