Q: My Mom is thinking of retiring at the end of the year. She is 62 years old and would not be entitled to Medicare until she is 65. Her employer has 25 employees. We were recently told by a family member that you can pick up Cobra insurance and keep it until you turn 65 and pick up Medicare as long as you are 62 when you retire. Is this correct? My mom would love to retire but does not want to worry about not have insurance coverage. A: Your mom would be eligible for COBRA continuation when she retires. Retiring is a qualifying event . When the qualifying event occurs the employee is entitled for up to 18 months continuation. 18 months is the maximum amount of time an employee can keep COBRA continuation. If the employee retires and is entitled to Medicare on the same date their spouse or dependent would be eligible for up to 36 months.