Why does "autofill from playlist" not work?

I have tried to autofill music onto my iphone from a playlist, but it will not allow me to, and gives a really unhelpful error message:
"iTunes cannot add any songs to the iPhone “x” because no songs in the playlist “x” can be copied to this iPhone."
I have autofilled music from the same playlist onto my phone before but this has never happened.... I have also seen this question asked before but with no answer as to why it does this or how to fix. Its really annoying and i'm pretty sick of spending hours searching for answers as to why itunes doesn't work every single time i want to put a new song on my phone. There may be a simple fix to this problem, but with absolutely no information as to why it happens it turns everything into an ordeal. nothing has changed with my phone or the itunes version since the last time i used autofill on this playlist. Another thing i have noticed is that when some music does copy over it does not retain any information regarding "skip when shuffling", so the box is always unchecked even when it is checked on itunes. I have looked for solutions to this and similar problems to no avail. I am so sick of this messing around - either use helpful error messages or fix ur frekking errors!
The worst part is this will probably just start working again for no discernible reason, like always i will still be confused and worried about whenever this may happen again. Thanks itunes!!

When I get the low on ink message I can usually still print, so I don't think that's the problem. Double tap the home button and see of the Printer app icon is in the recents tray. If you see the icon, hold down on the icon until it wiggles and tap the minus sign in the corner of the app to close it. Tap the home button twice.
Then unplug your router for about 30 seconds. Disconnect it from power, don't just press a reset button if it has one. Plug it back in. Then unplug the printer from power for about 30 seconds the same way - don't just turn it off using the power switch. Plug it back in. Reboot your iPad and then try again.
Reboot the iPad by holding down on the sleep and home buttons at the same time for about 10-15 seconds until the Apple Logo appears - ignore the red slider if it appears on the screen - let go of the buttons. Let the iPad start up.

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