Hello NickWoolven,
To help us better assist you, can you let us know more about the situation? You mentioned that there aren't any errors; is the issue that there just doesn't seem to be a response when trying to sync content? That information will help us plan how to proceed.
If you have iPod classic, iPod nano, or iPod shuffle: You have to sync your device with your Mac. There’s no other way to add content to it.
Please check out the following link, which has more information about syncing your devices using your Mac, and may help: Intro to syncing your Mac and your devices
Please also review this link to ensure the correct process is being used to sync your devices, so we can make sure there's not an issue there: Use the Finder to sync your iPhone, iPad, or iPod with your computer
Sync or remove content using the Finder
1. Open a Finder window and connect your device to your computer using a USB cable. Learn what to do if you don't see your device listed in Finder.
2. After your device appears in the sidebar of the Finder window, click the device to select it.
3. If prompted, trust your device. You might be asked to update to the latest version of iOS or iPadOS.
4. Select the type of content that you want to sync or remove from the horizontal list. To turn syncing on for a content type, select the checkbox next to “Sync [content] onto [user’s] iPhone.” More syncing options will now be available.
5. Select the checkbox next to each item that you want to sync.
6. Click the Apply button in the lower-right corner of the window. If syncing doesn't start automatically, click the Sync button. You may also be prompted to authorize your computer to complete the sync.
* You can only sync your device with one Apple Music or Apple TV library at a time. If you see a message that your device is synced with another Apple Music or Apple TV library, your device was previously connected to another computer. If you click "Erase and Sync" in that message, all content of the selected type on your device will be erased and replaced with content from this computer.
Thanks!
