Windows iTunes and iPhone issue

[Beitie]

I'm having an issue. Long story short, I've had my iTunes library moved from computer to computer, and I've kept everything since 2004. Now that I no longer have to worry about storage space on both my PC and my iPhone, I've decided to update some of my music to the Apple Lossless codec.

However, once I do this, the new files don't update to my iPhone when I sync, and if I attempt to play the songs on my iPhone, nothing happens. The songs are still shown in the Music app on my iPhone, with all the album art and such, but it's as if the file it self is missing.

So far the only way I've found to fix this is to completely restore my iPhone. That is not an ideal solution as some of my apps then break and need restoring as well, such as Microsoft Authenticator.

Has anyone else had this issue? Is there a simple or easy fix for this?

 

[Shirasaki]

Apple Lossless might not be supported on your iPhone. Another way to try to solve the problem is to convert those files into WAV. Largest file size but iPhone should support it. I hope you backed up your original library in full before going on with lossless conversion.

 

[Beitie]

Nope, it's not a file type issue. iPhones can totally play the Apple Lossless codec.

What I ended up doing was going into iTunes, un-checking the sync music button, and erasing all the music from the iPhone. Then once I made sure it was all off, I re-checked the sync music button. Luckily, it remembered all the playlists and artist, and albums I had checked before, and re-synced everything. Now I finally have Limp Bizkit - Nookie on my phone in lossless audio