By Qamar S, 15 years in US medical billing · Last reviewed October 31, 2026
Missing one date can cost you a year of the wrong plan or hundreds of dollars in lost FSA money. Pick the deadlines that apply to you and add them to your calendar in one click, with reminders a week and a day before.
Tick the deadlines that apply to you, then add them to your calendar. Each one comes with reminders 7 days and 1 day before.
The .ics file works with Apple Calendar, Outlook and Google Calendar. On a phone, open the downloaded file to add the events. Or use the Google Calendar links below, one at a time.
Private: nothing is sent to us. The calendar file is created in your browser.
Key dates at a glance
| Date | Deadline | Who it’s for |
|---|---|---|
| December 7, 2026 | Medicare Open Enrollment ends | People with Medicare |
| December 15, 2026 | HealthCare.gov deadline for January 1 coverage | People who buy their own insurance |
| December 31, 2026 | Use FSA money (calendar-year plans without rollover) | People with an FSA |
| January 15, 2027 | ACA Open Enrollment ends on HealthCare.gov | People who buy their own insurance |
| February 28, 2027 | Last day to switch after a Medicare Advantage plan ends | People whose plan didn’t renew |
| March 15, 2027 | FSA grace period ends (if your plan has one) | People with an FSA grace period |
| March 31, 2027 | Medicare Advantage Open Enrollment ends | People in Medicare Advantage |
| April 15, 2027 | Last day for 2026 HSA contributions | People with an HSA |
State marketplaces can have different ACA dates. California, New Jersey, New York and DC, for example, usually run later. Check your state’s marketplace.
From 15 years in billing: the deadline that catches the most people isn’t Open Enrollment. It’s December 31 for FSA money. Put it on your calendar now and book that eye exam or dental cleaning in November.
Frequently asked questions
When does Medicare Open Enrollment end for 2027 coverage?
December 7, 2026. Changes take effect January 1, 2027.
What is the deadline to enroll in ACA health insurance for 2027?
On HealthCare.gov, enroll by December 15, 2026 for coverage starting January 1. Open Enrollment ends January 15, 2027, with coverage starting February 1.
Do you collect my email for these reminders?
No. The reminders are added to your own calendar. Nothing is sent to us.
Sources: Medicare.gov: Joining a plan · HealthCare.gov: Dates and deadlines · IRS Publication 969
This tool is educational and is not legal, financial or insurance advice. MedBillGuide is not connected to Medicare, CMS or any government agency, and we do not sell insurance. See our Disclaimer.