Need help - Can't sync Music or Books to my iPhone

[RonT (aka Ombligo)]

I can't get my MBA to see my iPhone SE (2020). Both are up to date with software and I've tried both wifi and USB (multiple cables). Everything else syncs - notes, passwords, contacts, etc. The phone shows it charging as well - just won't load or sync books or music
I checked settings and everything seems to be correct, I have signed out of iCloud and back in, restarted both, googled and tried everything I could locate with no luck. I also tried my wifes iPhone and it doesn't see it either.

Any ideas?

Stupid question: Are you looking for the device-icon to appear in your Finder window sidebar?

Yes

Stupid question #2: Does the Mac prompt you to trust the device or cable?

No

Stupid question #3: Does the iPhone prompt to trust your Mac and enter your unlock-code when you connect it?

No

Stupid question #4: Does the iPhone icon appear in a Finder window sidebar after you opt to trust the connection and enter your unlock-code?

No


Asking about the Finder sidebar because if you haven't done it in awhile, you might be looking to sync via the Music app as was done via iTunes not long ago.

I'm listening.. not sure what you mean

[Fritz]

Perhaps the port has some funk in it. Maybe a little compressed air. Or close look with a sponge tip and isopropyl.

[RonT (aka Ombligo)]

Perhaps the port has some funk in it. Maybe a little compressed air. Or close look with a sponge tip and isopropyl.

tried that already

[special]

Some cables are for charing only, no data. Are you sure you are using a good cable (with data lines)?
Also try a new user account on the Mac.

[Fritz]

in re-reading, it seems it'd be a software issue. Perhaps sync got unchecked on iCloud for Music & Books.
I'm sure you did, but, toggling Sync for both Music and Books?

This is kind of a hardcore method. I've done a few times with Mail and it has been fine.
But Mail ain't media.
Be sure both are not listed in User/Login Items.
Quit both apps on the MBA.
Toss the plist for Music and books. Music (at least) will prolly show an empty library that you'll have to repopulate.
Books, dunno.
Restart.

/Users/omb/Library/Preferences/
com.apple.Music.plist
com.apple.bookdatastored.plist
com.apple.bookstoreagent.plist

Couple caveats, I do not own an iPho. I do not use Music.
My Macs are on Monterey (until I get the patience to go Seq).
I am not a doctor nor do I play one on TV.
I am not now, nor have I ever been a com'nest.
I believe all conspiracy theories are conspiracies themselves.

May the OS be with you.

[RonT (aka Ombligo)]

Thanks Fritz.

I've essentially reached that point where I'll visit the Apple Store on my next trip to Tampa. I've never had this issue before and wonder if it is something that occurred when I went to Sequoia. There isn't a huge hurry, I'd just like some books to listen to on vacation.

[Fritz]

seems a good idea and statement.

I have to update to Seq and am not looking forward to it for little annoyances.
Pro Tools, mostly.
Seq'll give me 2 years to upgrade to M silicon.