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How should I pay off my private student loans that have a lot of restrictions?
It doesn't make a whole lot of sense to save up and wait to make a payment on any of these loans.  Any dollar you pay today works better than saving it and waiting months to pay it, no matter which loan it will be applied to. Since your lender won't let you choose which loan your payment is being applied to, don't worry about it.  Just make as big a payment as you can each month, and try to get the whole thing out of your life as soon as possible. The result of this will be that the smaller balance loans will be paid off first, and the bigger balance loans later.  It is unfortunate that the higher interest rate loans will be paid later, but it sounds like you don't have a choice, so it is not worth worrying about. Instead of thinking of it as 5 loans of different amounts, think of it as one loan with a balance of $74,000, and make payments as quickly and as often as possible. For example, let's say that you have $1000 a month extra to throw at the loans.  You would be better off paying $1000 each month than waiting until you have $4000 in the bank and paying it all at once toward one loan.  How the lender divides up your payment is less significant than when the lender gets the payment.