iTunes won't sync songs

I just finished creating a playlist in my music library, and i have been trying to transfer it to my iPod Touch 3rd gen running iOS6 and my iPad 2 running iOS 7.1.1. They're not plugged in at the same time, but when i try to do either of them individually, nothing happens. The songs show up in Music under each respective device, but they are opaque with a little dotted circle to the far left for each. Now if i try moving a song from a different playlist or the main music library itself, same thing. Now i chose the Trust this Computer prompt i was given when plugging the iPad 2 in, didn't get that with the iPod. What's going on with this, i have never had this issue in the past with previous versions of iTunes, why is it happening now? Any help would be appreciated because i spent 4 days building this playlist and i would like to be able to use it.

The songs show up in Music under each respective device, but they are opaque with a little dotted circle to the far left for each.

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Can you screenshot this and post on here please?

Now i chose the Trust this Computer prompt i was given when plugging the iPad 2 in, didn't get that with the iPod.

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That's an iOS7 feature which is why the iPod didn't display that. But, so long as you opted to trust this machine, that won't cause you issues.

Which version of iTunes do you have?

i have never had this issue in the past with previous versions of iTunes

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Does this means you've never synced since updating to your current version of iTunes?

I wish i had taken a screenshot before, but i didn't cross my mind. I was able to figure it out with the iPod, at least do a work-around for it. I was trying to transfer the songs with a Mac Mini and so I transferred the songs to another computer, and that computer worked fine with the iPod, so unsure why the Mac couldn't do it, but my PC could.

As for the iPad, i have noticed that if i do an autofill for all the songs at once, which totals to 1800, it does the same thing, or gets to a certain number of songs then cancels the sync. So what i'm in the process of now is transferring the songs in chunks manually to the iPad, and it seems to be working from my PC. Still doesn't work on the Mac unfortunately.

But i have the latest version of iTunes on both machines, but the mini has 2GB of memory and my PC has 8GB, so i'm wondering if iTunes can't handle the amount of songs or something like that.

Well, I thought it was working with the ipad, but unfortunately i reached the same issue as i did with the autofill, where it won't transfer past a certain number of songs. It seems like the limit is around 800 songs, is this normal?

The number of songs is only limited by the space you have available on the device.

Could really do with that screenshot.

Have are you syncing the playlist exactly? Are you selecting the device - Music from the top bar, then ticking Sync Music - Selected playlists, artists, albums, and genres - ticking the playlist required then hitting sync?

It's worth noting that a device can only sync to one library . . . is the library on the iMac the library the devices have synced with in the past?

Ok, i think i hope this screenshot will help then:



That is what happens when i press sync when i try to autofill. It cancels the sync and i get what is seen here.

Interesting you said that about syncing music across different computers. Because my ipod is synced to the Mac, but i was able to transfer the music from my PC over without issue. Now the iPad is synced to this PC, and i still have the issue.

Something has corrupted the library file. The easiest way to resolve the grey dotted circle issue is to recreate your library:

iTunes: How to re-create your iTunes library and playlists

Sorry for the delayed response, I gave it a go on the Mac for its library, i don't think it's worth doing on the PC because my other devices sync the same playlist just fine. Unfortunately it didn't make a difference at all.

You completely rebuilt the library and you still have the same grey dotted circles?

Are the files actually there on the disk?

Yes, I manually manage where all my music is, so i know exactly where it is. Yea, I did notice that, contrary to what the original screenshot was, that it seems to cap how many songs i can have on there at 1000. Because i was able to get it going, but it stopped at 1003. After that, i tried individually adding them by groups, and it still stopped at the same number, even when i started at different songs. I have never seen that before, like my ipod touch doesn't do that, and it's smaller than this is.