The vast majority of the people who "can't figure it out" are employed by the Department of Education or by FedLoan Servicing. I am employed by the U.S. government, recertify for an eligible repayment plan every year, am enrolled in autopay, and still get told that I've only made 9-10 qualifying payments in a year-long period. I often have to spend hours on the phone, across several months, arguing and documenting, just to set the record straight.