How long does COBRA last? Crystal April 03, 2018 19:54 Updated You may be able to remain insured with your health plan for up to 18, 29, or 36 months. Related articles How do I enroll in COBRA? When will COBRA coverage end? Who is eligible for COBRA? What is the longest amount of time I can be enrolled in COBRA? When is COBRA subject to be canceled for non-payment?