Some people get medicare automatically and some have to sign up you may have to sign up if youre 65 or almost 65 and not getting social security there are certain times of the year when you can sign up or change how you get your coverage if you sign up for medicare part b when youre first eligible you can avoid a penalty. Most people should sign up for medicare when they first become eligible during their initial enrollment period the initial enrollment period begins three months before the month you turn 65 includes your birthday month and extends for three months after your birthday month. Generally we advise people to file for medicare benefits 3 months before age 65 remember medicare benefits can begin no earlier than age 65 if you are already receiving social security you will automatically be enrolled in medicare parts a and b without an additional application. Some people get medicare automatically but some dont and may need to sign up i have employer coverage find out what you need to do if you have employer coverage and youre turning 65 are over 65 are under 65 and have a disability apply for medicare online apply online for medicare on social securitys website. When can i sign up for medicare supplement insurance medicare supplement plans also called medigap plans are sold by private insurance companies if you enroll in a medigap plan during your medigap open enrollment period medicare supplement insurance companies cannot charge you higher premiums or deny you a policy based on your health