I found that anything I recorded and encoded with Audacity did not work, as well as Vanessa Carlton's Heroes & Thieves album and the Rent (Film Soundtrack) album. To work around this issue directly with new Audacity stuff, I guess export as ALAC and then follow Step 9 and on. This issue occurs on the Windows and Mac versions of iTunes and is probably due to some change in the AAC decoder Apple made. iTunes skips the songs and reports their length as 789:57:13. m4a container - which is FFmpeg version 2.2.2 Audacity requires (even to this day). I found the latest iTunes wouldn't play things encoded with Lavf55.33.100 AAC in the. iTunes and the iPhone seemed to be OK with the songs renamed to. An alternate (easier) work around is to rename the songs as. This guide is for Windows specifically, but Mac will have very similar steps. You have to play them to get their time to be correct - but now they work again. Note: I've found that in Windows' iTunes 12.9.5.7 the songs are playable again.
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