Songs becoming Grayed-Out in iTunes

I'm asking you to perform an experiment in the hopes that it might resolve things for you. If I had the same symptoms as you I could try the experiment myself, but I don't so I can't. Can I be sure it will help? No. Is it what I would do in your situation? Yes.

We covered some of this before, but I'll reiterate. I'm a fellow user trying to help out. I don't have a detailed inside knowledge of the processes involved in the iTunes syncing mechanism. I cannot explain why you have the issue that you do. All I can do is try to help you find a workaround. This is an iOS issue, which is why you've never run into it with your classic. Since it appears to be related to purchased content rather than ripped media it is worth investigating the impact of signing out of the iTunes Store on the device on the subsequent sync behaviour. It may allow tracks that currently show with the grey dotted circles to fully sync to the device and show with your preferred metadata. Or not. The only way to find out is to try it. And if it doesn't help, try the other experiment. Or do that one first. But do something other than asking me to explain a bug I have no control over or predict if this is a procedure you'll need to repeat. You can cross that bridge if you get that far.

tt2