How does Medicare and Social Security disability go hand in hand? So, first of all, Medicare benefits will not kick in if you have an SSI only claim. Medicare only connects to an SSDI claim. So, if you’ve applied for Social Security disability income and you win your benefits, basically 2 years from that date, 24 months after your win date, then your Medicare automatically kicks in and you’re covered with income under your benefits from SSDI and you’re going to be covered for health insurance under Medicare. So, it’s a fantastic match. Goes hand in hand and will cover you for as long as you have a disabling condition.