Hey MacRumors, I've been dealing with this problem for a while now, and despite asking for help in a few places, no one seems to know what's going on. I'll start off with the specs: iPod Classic - 5th gen - 80GB - purchased new in April 2008 - has been manually managed from day one Samsung laptop running Windows 8.1 - unsure of model number, but was purchased in August 2013 iTunes 184.108.40.206 I guess the problem really started in June 2016. One day I tried connecting my iPod to my computer so I could add a few songs to it. Problem was, neither iTunes or my computer recognized my iPod - it didn't appear at all in My Computer or iTunes. After I disconnected my iPod, all the music, photos, and videos somehow vanished from my iPod. My brother has a Macbook, so he tried connecting it to his computer. It didn't work on his computer either, though Disk Utility in OS X showed that the volume wouldn't mount. He tried fixing it with DiskUtil - no bueno. A few months later he was tinkering with it when he found out there were 4 pending sectors. I believe he cleared the pendings, which fixed the issue. (I'm not really sure what that means, but it helped.) Both iTunes and our computers recognized the iPod and I was able to re-add all my songs to my iPod. Now, to my current issue: January 9 - I charge my iPod by connecting it to my computer, and while I charge it, I like to check out its Last Played list on iTunes. On this day iTunes froze when I connected my iPod to my computer. After it unfroze, iTunes showed that the last time I listened to any songs was on December 29, 2016. This was wrong as I had listened to many songs since that date. I'm almost certain I updated iTunes on December 29th, the last day it had been connected to my computer/iTunes. I'm not sure if this has something to do with the Last Played list not updating. I should note that I listened to a few songs while my iPod was connected to my computer. These songs appeared in the Last Played list. January 10 - I reset my iPod to see if it would help. I listened to a few songs, then connected it to my computer again. Surprisingly, the songs I had just listened to showed up in the Last Played list. January 13 - After listening to a few albums since the 9th, I connected my iPod and checked the Last Played list to see if it was still updating. To my dismay, it stopped updating the list. January 20 - Connected it to my computer again to see if the Last Played list was updating. iTunes froze as soon as I connected the iPod. When it unfroze, a "Welcome to your new iPod!" screen appeared. I pressed 'cancel.' My iPod wasn't showing up at all on iTunes, but it was listed under My Computer->Devices and Drives. January 28 - I updated iTunes to 220.127.116.11 and wondered if my iPod's Last Played list was still not updating. The list said I hadn't listened to anything since January 13, which was incorrect. After ejecting and connecting my iPod a few times, my iPod suddenly reset itself immediately after I ejected it, but hadn't unplugged the USB cord. After it rebooted, it reconnected itself to the computer. I ejected the iPod and I listened to a few songs, then reconnected it to my computer. The Last Played list finally updated and showed the songs I had just listened to a few minutes prior. Interestingly, iTunes didn't freeze when I connected my iPod, whereas it did on every other occasion. January 31 - Connected my iPod again and checked the Last Played list. Every song I listened to since the 28th showed up in the Last Played list! I finally thought the problem had fixed itself. Today (February 3) - Wanted to check if the Last Played list was still acting up. Sure enough, iTunes froze, and the Last Played list said I last listened to music on January 31st. And sure enough, it was wrong. As I write this, my iPod is connected to my computer and I'm listening to a few songs on iTunes. Each song I listen to from my iPod is appearing in the Last Played list. Why are the play counts being updated when it's connected to my computer, but not when it's disconnected? I'm at my wit's end. I've searched all over the internet for people who have had the same issue as me. Everything I've found is either very old, or people say that manually managed iPods shouldn't even sync the play counts in the Last Played column. My iPod has been manually managed since day one, and every single song I listened to appeared in the Last Played list until December 29, 2016. Does anyone have any suggestions on how to fix this? Many thanks in advance.