Q: If my cobra ins runs out April 30, I know I have a 30 day grace period to pay(to decide if I want to pay for the cobra). If I need to use the cobra before I elect to continue cobra in the 30 day period and I pay the premium in the month of May, will the coverage retro back to the date I need it to if it is in the 30 day grace period after termination of employee and ins.? A: If your COBRA payment is not made in a timely manner, or within the 30 day grace period than you are risking termination of your COBRA rights and coverage. If you do make the payments with in the time allowed you will not lose coverage, but will still need to pay the later months coverage. If is best to communicate with your COBRA administrator about payment that may not be made on or before the due date.