iPod Sync Issue Causes OS Freeze and Music Loss on MacBook Pro

Hi! I have two MacBook Pros: a mid-2021 and a mid-2012. Both have SSDs with ample storage space. The newer machine isn’t an issue here.

I basically keep the mid-2012 around for two reasons: iTunes (it has the latest OS that supports it) and Photoshop (it came with a licensed copy). I’m an old-school guy in many ways; I’ve been using 7th-gen iPod Classics almost nonstop for nearly 17 years.

My current iPod is a standard 160GB 7th-gen model. It has never given me even the slightest trouble until today. It is nearly full with over 25K songs, but has consistently worked fine during the time I’ve had it.

This morning I downloaded some mp3 tracks for a college choir reunion. There’s nothing wrong with the files themselves. I imported them into iTunes and then connected my iPod and hit Sync.

After a couple of minutes I noticed that iTunes didn’t seem to be moving beyond the “Starting Sync” message. It has occasionally gotten stuck there in the past; I’ve always disconnected the device and retried it. Sometimes it wouldn’t recognize the iPod when I plugged it back in and I would have to restart the computer, but it would always work eventually.

This time it didn’t recognize the iPod so I figured, just restart it. I told the computer to restart and gave it a couple minutes. It did nothing. I turned it off manually and restarted; it still wouldn’t recognize the iPod. I turned it off again and went to work.

Got home from work, turned the computer back on. Now not only does it not recognize the iPod, but the OS freezes up. I right-click on the screen background and nothing happens. I try to open a Finder window and it never comes to the front. The taskbar at the top that includes the System commands doesn’t show up. I have to force the machine off by holding down the power button.

Not only this, but my iPod now doesn’t think it has any music on it. It had over 25,000 songs this morning; they couldn’t have been wiped in two minutes. I must’ve unplugged the device at the exact wrong time in whatever it was doing, is all I can think of.

The computer and the iPod have both been extremely reliable up till now; I don’t find it feasible that they both just suddenly decided to quit simultaneously. But I’m at my wit’s end as to what I’m going to do. I will listen to the choir tracks on my phone but I do want to get back to having a working iPod and being able to use both laptops. Any ideas?

[Re-Titled by Moderator]