Mobile Sync Requires Server Update On Up To Date Server

I’m running Windows 10 and syncing to an Android phone. Most of my music has synced properly but there are a few seemingly random songs that state a “Server Update is Required,” so they sit there “Waiting to Download.”

The server is already up to date. I’ve tried both automatic and manual installs, but the problem remains. Please advise, thanks.

Now it won’t sync anything without a “Server Update,” but the server is up to date. Everything is “Waiting to Download.”

UPDATE: I reinstalled the Android app, deleting everything and starting over. Sync seems to be working again, but it’s annoying nonetheless.