This iTunes sync issue will kill me

[puma1552]

This has been the absolute bane of my existence for three ***** years with this iPad Air 2. iTunes 12.7.1.14, iOS 10.3.3.

-I buy song off iTunes (Havana by Camilla in this case) with my Apple ID on my computer where my master library is.

-I add song to playlist in iTunes.

-I add playlist to iPod classic, iPhone 8, and iPod nano 7G with no issues whatsoever.

-I add playlist to iPad, and I get this garbage when looking at the playlist on the iPad in iTunes:

This grayed out/dashed circle garbage. Song does NOT transfer to iPad.

What the hell is the deal here? I've been fighting this on this iPad for three years, across multiple builds of iOS and multiple builds of iTunes, so software version sure doesn't seem to matter. It ONLY affects my iPad, and it's a chronic problem that rears its head every so often for no rhyme or reason - other songs, no problem, some songs, this problem. I have plenty of free space on the iPad.

I have wasted hours upon hours upon hours of my life on this problem with this iPad, to the point I'm about to just trash the library on it altogether and give up putting music on it at all.

The *ONLY* solution I have ever found to this is a full blown complete restore of the iPad and setting it up as brand new, which is a massive hassle for a problem that rightfully has no reason to exist. This is an iTunes song, bought from Apple, on a Mac, syncing to an Apple device.

ANY ideas on this? This will kill me. I don't know if the iPad is just straight garbage or what because I never had this on my iPhone 6, iPhone SE, or iPhone 8, all of which I've had during the period of ownership on this iPad.

 

[strawberryshortcake]

This has been the absolute bane of my existence for three ***** years with this iPad Air 2. iTunes 12.7.1.14, iOS 10.3.3.

-I buy song off iTunes (Havana by Camilla in this case) with my Apple ID on my computer where my master library is.

-I add song to playlist in iTunes.

-I add playlist to iPod classic, iPhone 8, and iPod nano 7G with no issues whatsoever.

-I add playlist to iPad, and I get this garbage when looking at the playlist on the iPad in iTunes:

This grayed out/dashed circle garbage. Song does NOT transfer to iPad.

What the hell is the deal here? I've been fighting this on this iPad for three years, across multiple builds of iOS and multiple builds of iTunes, so software version sure doesn't seem to matter. It ONLY affects my iPad, and it's a chronic problem that rears its head every so often for no rhyme or reason - other songs, no problem, some songs, this problem. I have plenty of free space on the iPad.

I have wasted hours upon hours upon hours of my life on this problem with this iPad, to the point I'm about to just trash the library on it altogether and give up putting music on it at all.

The *ONLY* solution I have ever found to this is a full blown complete restore of the iPad and setting it up as brand new, which is a massive hassle for a problem that rightfully has no reason to exist. This is an iTunes song, bought from Apple, on a Mac, syncing to an Apple device.

ANY ideas on this? This will kill me. I don't know if the iPad is just straight garbage or what because I never had this on my iPhone 6, iPhone SE, or iPhone 8, all of which I've had during the period of ownership on this iPad.

EDIT: Answer the following question first:
(1) Is your lightning transfer cable the official apple cable?
(2) Is your lightning transfer cable connected directly to your computer USB port?

Reason for the above is because even though my 3rd party 10 foot cable worked to transfer and sync videos just last week and a couple months ago, today I was not able to successfully transfer because I kept getting the error message saying that my ipad is disconnected. Once I hooked up my apple lightning cable directly to my PC, everything went smoothly.


Make sure you have a back up of the song somewhere.


Try the following below (after my little rant) ... because I just re-encountered this massive headache that I thought I had solved a couple months ago.

This "sync and transfer" concept is the ONE thing that I hate about the apple ecosystem. iTunes is the absolute worst piece of software that I have ever encountered. Transferring files from the PC to the iPad should be simple, but it's not. The tried and true "drag and drop" system mimics real world physical actions ...

... I've got a bunch of paper on my desk and I want to give them to my colleague at the next cubicle. I simply pick up the papers and deliver them by hand. The simple "drag and drop" method. But nope, apple needs to develop a complicated system to get the job done because iTunes is supposedly more "intuitive" for their user base. iTunes and intuitive both starts with the letter "i" but they definitely do not go hand in hand.

I don't know if the following will work for you, but this is what has worked for me when it comes to these greyed circles. I mostly transfer videos (i.e. DVR primetime television shows, youtube videos, my DVD sitcoms, etc.). It should also work for failed music transfers.

You must delete the attempted transferred song/video from your iTunes library first. Then press the sync/done button at the homescreen of iTunes. This should let iTunes know that you want your iPad "without" the failed transferred song. Now, go ahead and reupload the song using the "file" ---> "transfer to library" --> "sync"/"done."

I'm not sure if you can read the following. If not, press control + on your PC (to reverse the effect, simply press control - )

 

[puma1552]

I was using the official Apple cable and it was plugged directly into my computer's USB port.

Thanks for this. Oddly enough I was able to solve this problem relatively simply last night after years of struggling with this. The song showed up just fine in my iTunes library both in the library songs list as well as within the playlist I added it to, but once I dragged and dropped that playlist to the iPad in the left side bar, only in there was it grayed out.

Ultimately what I did was delete it completely from the iPad, and then instead of transferring it to the iPad by loading a playlist to the iPad with the new song, I manually transferred the song from the iTunes library song list directly to the iPad library by dragging and dropping. That worked, and then I was able to transfer the playlist to the iPad and it worked. For whatever reason trying to add the song by adding a playlist to the iPad was the problem rather than manually moving the song over from library to library first.

I really feel like Apple should know about this by now, I know this has been the bane of many peoples' existences for a while with iTunes, which is, as you said, a terrible piece of software.