Greetings Ryan_Art,
To help isolate the behavior, see if file transferring works as expected while using a different macOS user account. This will help see if the issue is system-wide.
Check out those steps here: Set up users, guests, and groups on Mac - Apple Support
"Add a user
- On your Mac, choose Apple menu > System Preferences, then click Users & Groups .
- If the lock at the bottom left is locked , click it to unlock the preference pane.
- Click the Add button below the list of users.
- Click the New Account pop-up menu, then choose a type of user.
- For more information about the options for each type of user, click the Help button in the lower-left corner of the dialog.
- Enter a full name for the new user. An account name is generated automatically. To use a different account name, enter it now—you can’t change it later.
- Enter a password for the user, then enter it again to verify. Enter a password hint to help the user remember their password.
- Click Create User."
To further troubleshoot, see if there's an update available for the drive on the manufacturer's website, and test while having other peripherals disconnected. You can see those suggestions here: If a USB device doesn’t work with Mac - Apple Support
Additionally, it's expected behavior for safe mode to not detect some USB devices, as outlined here: How to use safe mode on your Mac - Apple Support
Kind regards.