Why is the "sync" option greyed out in my iTunes?

Is your iPod already synced to another computer? It can only be synced to one at a time. Alternatively, is the software on your iPod up to date? If not, it can have problems syncing with iTunes. Also, go to Preferences > Devices and make sure that you have not checked the “Prevent iPods, iPhones, and iPads from syncing automatically” box.

If none of these things work, you can still add music to your iPod manually. Syncing is just a more automatic way of doing things.

I did sync it with my work computer… How do I fix that?

Also, it did allow me to drag all the music into the iPod folder under My Computer but none of it shows up on the iPod.

If you’re going to add music manually, you want to do it in iTunes. It won’t show up otherwise. As for unsyncing the iPod, does an alert box pop up when you plug your iPod in asking if you want to erase the contents of the iPod and sync with the new computer? That is one way of doing it, though it will now mean that you can’t sync with your work computer.

If you’d like to be able to use the iPod with both computers you need to refrain from syncing with either. Plug the iPod back into your work computer and go to Preferences > Devices, select your iPod, and check the box for “Manually manage music and videos” (this option might also be available by clicking on the iPod in the iTunes sidebar). You might have to unsync the iPod from your work computer before anything else will work.

This is based on slightly older versions of iTunes, but assuming they haven’t changed too much…

If you’ve already dragged all of your music into the iPod folder, try going to File > Add Folder to Library. Once you’ve done this for all of your music, it should show up under Music. When I do this to a large amount of files, I tend to do it in smaller chunks, so that there’s less risk that I have to interrupt the process while it’s in mid-transfer.

Also, be aware that if you sync your iPod with this computer, you will probably lose the files that were synched with your work computer. If you are using an external hard drive, and using it on both computers, you’ll need to tell iTunes where to look for your music, or it will simply copy all of your music into your C drive. To change the directory where iTunes finds your music, go to Edit > Preferences > Advanced, and under “iTunes Media folder location”, click Change to browse to your external hard drive.

If you are using an external hard drive, make sure you always plug it in before opening iTunes, or iTunes will sometimes switch the music back to your C drive, and try to create a new library based on that (even if you have nothing there). Or it will show you your songs, but not let you play them because it can’t “locate” them. It’s just one more thing you have to be mindful of.

Also, managing music on two separate computers means updating the library every time you switch, so be careful to add any new files to the library after switching – or these won’t show up in your music, and they’ll be removed from your iPod when you sync. In general, I find it’s a lot simpler to keep all music files on a single external hard drive, and sync my iPod with only one computer.