Syncing newly imported content to iPhone not working (iTunes)

[Antaris]

Hi! Part of my issue is likely stemming from the fact that I am setting up my (Windows 11) laptop as a second syncable device. When I set up my iPhone originally, I did this on my main desktop (Windows 10). So I might try using it later today, but am hoping to go back and forth between both Windows PCs...

I used iTunes to import three new CDs I'd purchased onto my laptop, which I had not used for syncing before. I authorized the laptop, imported the discs, copied the imported folders into "~\Music\iTunes\iTunes Media\Music\" where the rest of my library is. (iTunes puts the albums into "Audiobooks", which took me a moment to find.)

I then go into Apple Devices and ran a sync - in the settings/music panel option on the left, I get the message I am using Cloud Music Library. I tried to turn this off on the phone, but got a disclaimer that all the content on my phone would be deleted so I said 'no'. Should I turn off syncing on the phone, then turn it back on? (I just looked at my Music folder and saw that sync had added a folder that wasn't there before, but my new albums still aren't on the phone.

I also set up "iTunes Match" on the laptop, which I'd set up on my main desktop back in October, just to be sure. The button was clickable, I added it, then the button grayed out. I did reboot the laptop and went back into iTunes, and saw "Add this computer" button light up again in iTunes Match. Do I need to click on this again?

 

[Antaris]

I think I might have this figured out...

1. In Apple Music, drag the imported files from Windows explorer into your iTunes/music library
2. make sure you're logged into Apple Music. If not, log out then log back in - then the "updating cloud library" should commence instantly.
3. When that's done, let the phone sit as it's probably got more syncing to do - drink caffeine at your own peril
4. enjoy 😀

I will definitely get the hang of this; it's the biggest learning curve compared to Android (just plop files into the folder) but it's at least iTunes Music is backed up to iCloud and not just on the local device, without going through a rather different set of hoops and hurdles that I never used... (plus, iTunes Match has been awesome since day one for my initial library setup...)