Hey there and welcome to Apple Support Communities CPadin,
We can certainly understand your concern and can help provide some insight.
We recommend checking out these steps for more information on how to sync audiobooks between your Mac and iPhone, iPad, or iPod touch and see if it matches up with your procedures.
" Sync audiobooks to your device
- Connect your device to your Mac.
You can connect your device using a USB or USB-C cable or using a Wi-Fi connection. See Sync content between your Mac and iPhone, iPad, or iPod touch over Wi-Fi.
2. In the Finder
on your Mac, select the device in the Finder sidebar.

If you connect your device to your Mac using a USB cable and don’t see the device in the Finder sidebar, see If your device doesn’t appear in the sidebar.
3. Click Audiobooks in the button bar.

4. Select the “Sync audiobooks onto [device name]” checkbox to turn on syncing of your audiobooks.
With the checkbox selected, syncing is set to transfer all your audiobooks to your device.
![The “Sync audiobooks onto [device]" checkbox is selected. Below that, “All audiobooks” is selected to the right of Sync, above “Selected audiobook](https://help.apple.com/assets/63BCA927AAE78C58DD7FBE35/63BCA92EAAE78C58DD7FBE76/en_US/68918d33abff26a9304ea7db017aba54.png)
5. To sync a selection of audiobooks, click “Selected audiobooks.”
6.Select the checkboxes for the individual audiobooks you want to sync in the Audiobooks list. Deselect the checkbox for any audiobooks you don’t want to sync.
7. When you’re ready to sync, click Apply.
You can choose to sync your Mac and your device automatically whenever you connect them. See Turn automatic syncing on or off on Mac.
Before disconnecting your device from your Mac, click the Eject button
in the Finder sidebar. "
For additional information, check out this link: Sync audiobooks between your Mac and iPhone, iPad, or iPod touch - Apple Support
Kindest regards!