Offer your insights or judgment on the input financial query or topic using your financial expertise. Reply as normal question answering

How should I pay off my private student loans that have a lot of restrictions?
The one thing that I saw in here that raised a big red flag is that you said you "overpaid" on your interest.  ALWAYS make sure you tell them that any extra money should be applied to principal only, not to interest.  You accrue interest based on your outstanding principal amount, so getting that lower reduces the overall amount of interest you end up paying.  Paying the interest ahead saves you nothing.  However, make sure you pay the current interest owed that month. They can capitalize past due interest - in affect, change that to be considered an addition to the loan principal amount and you end up paying interest on the interest.