To retake the CISSP re-examination, you have to buy a CISSP Exam Peace of Mind voucher to retake the examination after 30 days of your first exam attempt.. CISSP allows multiple exam retakes within a year, allowing up to a maximum of four attempts within one year of your first exam. Once you obtain the passing scoe, you won’t be able to retake the exam. The first CISSP exam reattempt: After 30 days of test-free days.Second CISSP exam reattempt: After 60 test-free daysThird CISSP exam reattempt: After 90 test-free days.Fourth CISSP exam reattempt: After 180 test-free days. If you do not pass the CISSP exam on your fourth attempt, the reattempt dates will reset and it will be the same as before.