iPod AACs that won't sync

[apfhex]

I'm trying to figure out why a group of songs just will not sync to my iPod Shuffle (1st gen). The only connection I could find between these few songs is that they were all converted from FLAC to AAC using Toast. Is Toast making incompatible AAC files? However, I swear some other songs I also converted using Toast DID sync to my iPod... in fact I know this to be the case. I always use the same settings in Toast, so why would only some of them not sync? The files are linked properly in the Library — iTunes plays them fine. They're not un-checked. They don't have any weird characters in the file names. I just don't know.

 

[mad jew]

As a test, use iTunes to convert one of the already converted AACs to the exact same format and bitrate. Does the new version sync?

 

[apfhex]

Yeah, they sync if I convert them again in iTunes, so it must be a problem with how Toast converted them (it's a pain if I have to re-rip the affected tracks, but...). I used the same settings every time (256k VBR, 44.100kHz), so I don't know why some don't work.