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It's really simple to sum up. My iPad and computer are on the same Wifi. I put my local files not available to stream in a playlist, and I marked that playlist to be available offline. All the songs are stilled greyed out on my iPad, and when I click one, my iPad says the song is not synced. The local files playlist on my iPad is also empty. When I try to google this, all of the posts I find are from 2014. So, I'm worried that I'm the only one facing this problem.
**UPDATE**: Fixed the issue. Apparently, my house has two wifi networks, both with a similar name, but both devices were connected to two different networks. However, with my songs synced, there is no album artwork for my synced local files. Is this normal, and if it not, how can this be fixed?
Solved! Go to Solution.