I found a fix to this EFFING ISSUE after my 7th attempt. #nevernevernevergiveup
Step 1. Format the Hard Drive to ExFAT format (make sure you have enough storage capacity #captainobvious)
Step 2. You HAVE TO sync the Trophies (wtf). Go to [Trophies], press the Options button, and choose the [Sync With PlayStation Network] option
Step 3. Insert the USB storage ...