A guide
to annual

Losing health coverage? Need to apply for a plan? Keep reading for resources to help you find coverage.

Woman wearing white tank sitting on the couch smiling while looking at a computer tablet.

What is the Annual Enrollment Period?

People who get Medicare need to know the facts about this important enrollment window. Cityblock gives you the basics in under a minute.

How do health plan enrollment periods work?

Health insurance can be complicated. To start your journey, think about which group of statements below best describes you.

Frequently Asked Questions

I’m a Cityblock member, and I’m worried I’m losing my healthcare. Can my care team help me?

Your Cityblock team is here for you. If you’re losing health coverage, they can connect you to state and federal resources that can help.

I’m turning 65 soon, or just turned 65. Can I still enroll during Medicare Annual Enrollment?

Short answer: yes! 

People who are about to turn 65, or who just did, have an enrollment window called the Initial Enrollment Period. This is your personal window to join Medicare for the first time. Whenever it happens, you can enroll in Original Medicare, Medicare Advantage, and/or Medicare Part D (Prescription Drugs).

I have Medicare, but I missed AEP! Is there another time I can make changes to my plan?

If you missed AEP, don’t worry. You may still be able to make changes to your health coverage.

Here are some of the other windows for enrollment in Medicare plans:

  • Medicare General Enrollment: General Enrollment runs from January 1st-March 31st every year. 
  • Special Enrollment Periods: When certain life events happen, you’ll qualify for a Special Enrollment Period. These windows to enroll in new health insurance can happen at any time of year, and don’t involve paying extra fees. Some examples of events that can lead to a Special Enrollment Period include: your current plan not being offered for the next year, getting married or divorced, moving. gives more details here about the different types of Medicare enrollment periods. Visit this page for a more detailed list of life events that trigger a Special Enrollment Period.

Can I ever enroll in a new health plan outside of the enrollment windows above?

If you become eligible for Medicaid, you can enroll at any time of year. This is also true for CHIP.

If you aren’t eligible for Medicaid, you can enroll in new health coverage when certain life changes happen. This is true whether you get Medicare, insurance through work, or have a plan through the Marketplace. These are called qualifying events. They include changes to your life and household like:

  • • Moving 
  • • Losing your current health coverage
  • • Getting married or divorced
  • • Having a baby or adopting a child
  • • Change in income

When you have a qualifying event, you qualify for a Special Enrollment period. This Special Enrollment Period can happen at any time of year. Learn more about Special Enrollment Periods for all types of healthcare.

I'm not a Cityblock member. Can you help me?

If you’re not a Cityblock member, you can still get personalized help enrolling in a new plan. has a tool that connects people to local enrollment help. Visit the tool and enter your zip code. 

We’re here to help

Whether it’s to learn more about our services, ask questions about your membership, or to schedule a visit, call us—we’d love to hear from you. We’re available Monday - Friday, 8am - 8pm ET.

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