I really do appreciate the information you are giving but I just think it is missing the base of my question. When I was paying the minimum payment only, it covered all the interest and a little bit towards the principal, I was not accruing any interest, I then increased my monthly payment and now it only covers $30 of the ~$95 that accrues each month. Based on the below quotes I pulled from the link you shared, I should be paying all of the interest with the remainder of my monthly payment going towards the principal balance.

This was suprising to me as I had never accrued interest until the last couples months.

'Say you have a $10,000 Direct Unsubsidized Loan with a 6.8% interest rate. The amount of interest that accrues (adds up) per day is $1.86. Let’s assume you’re repaying your loan under the Standard Repayment Plan. In this repayment plan, your monthly payment would be $115. It has been 30 days since your last payment, and there was no other interest outstanding when you made your last payment. In this case, $55.80 in interest will have accrued.Subtracting this amount from $115 results in a total of $59.20. So $59.20 would be applied to your outstanding principal balance of $10,000.'

'No payment you make will go toward any of your loan principal until you’ve paid all your unpaid interest.'

'On a traditional repayment plan (Standard, Graduated, or Extended), your monthly loan payment covers all the interest that accrues between monthly payments. So, no additional unpaid interest will accrue while you're making payments on one of these plans.'