Open Enrollment Checklist: Don't Miss These Deadlines

Missing open enrollment deadlines can leave you without coverage or stuck with a plan that doesn't meet your needs. Here's your comprehensive checklist for all major enrollment periods.

Health Insurance Marketplace (ACA)

When: November 1 - January 15 (for coverage starting January 1)

Mark Your Calendar:

• November 1: Enrollment opens

• December 15: Deadline for January 1 coverage

• January 15: Final deadline for coverage starting February 1

What to Do:

• Estimate your household income for the coming year

• Review subsidy eligibility at Healthcare.gov

• Compare plan metal levels (Bronze, Silver, Gold, Platinum)

• Check if your doctors are in-network

• Verify your prescriptions are covered

• Calculate total annual costs (premiums + out-of-pocket)

• Enroll and make first premium payment

Special Tip: Small income changes can significantly affect subsidies. Estimate conservatively and report changes promptly.

Medicare Annual Enrollment Period (AEP)

When: October 15 - December 7 (for coverage starting January 1)

Mark Your Calendar:

• October 1: Medicare plan previews available

• October 15: Enrollment begins

• December 7: Enrollment ends

What to Do:

• Review your current plan's Annual Notice of Change

• Check if your doctors are still in-network

• Verify your medications are still covered

• Compare plan costs for the coming year

• Review Medicare Advantage vs. Original Medicare + Medigap

• Check prescription drug plan formularies

• Evaluate extra benefits (dental, vision, hearing)

• Make changes if needed

Special Tip: Even if you're happy with your current plan, review it. Plans change coverage and costs annually.

Medicare Initial Enrollment Period (IEP)

When: 7-month window around your 65th birthday

Timeline:

• 3 months before your birthday month

• Your birthday month

• 3 months after your birthday month

What to Do:

• Determine if you should delay (still working with employer coverage)

• Decide between Medicare Advantage or Original Medicare + Medigap

• Choose a Part D prescription drug plan

• Enroll in Part B (if not automatically enrolled)

• Consider Medigap if choosing Original Medicare

• Get confirmation of all enrollments

Critical Warning: Missing this window triggers lifetime late enrollment penalties for Part B and Part D.

Medicare Special Enrollment Period (SEP)

When: 8-month window after employer coverage ends

Triggers:

• Losing employer coverage (you or spouse retires)

• Moving outside your plan's service area

• Qualifying for Medicaid

• Nursing home entry/exit

• Chronic condition diagnosis (for certain plans)

What to Do:

• Document the triggering event

• Act within the 8-month window

• Submit proof of previous coverage

• Choose new coverage

• Confirm effective date

Employer Open Enrollment

When: Varies by employer (typically October-December)

What to Do:

• Review benefit changes for the coming year

• Recalculate family needs (new baby, aging out dependents)

• Compare HDHP+HSA vs. traditional plans

• Maximize HSA or FSA contributions

• Review life and disability coverage

• Update beneficiaries

• Enroll in voluntary benefits if needed

• Confirm elections before deadline

Special Tip: Don't auto-enroll. Review annually—family situations and plan options change.

Marketplace Special Enrollment Period (SEP)

Qualifying Life Events:

• Loss of health coverage

• Marriage or divorce

• Birth or adoption

• Change in residence

• Change in income affecting subsidies

• Gaining citizenship or legal status

Timeline: 60 days from the qualifying event

What to Do:

• Document the qualifying event

• Apply within 60 days

• Submit required proof

• Choose coverage

• Pay first premium

COBRA Election

When: 60 days after job loss or qualifying event

What to Do:

• Receive COBRA election notice

• Compare COBRA cost to Marketplace plans

• Check if you qualify for subsidies (often cheaper than COBRA)

• Elect COBRA if needed within 60 days

• Pay initial premium (can be backdated)

Special Tip: COBRA is often expensive. Losing job coverage is a Marketplace qualifying event—compare options.

Important Reminders

Income Changes: Report within 30 days to Marketplace if:

• You get a raise or bonus

• You lose income

• You add/lose a household member

• Your dependent's income changes

Documentation to Keep Handy:

• Social Security numbers

• Income documents (pay stubs, tax returns)

• Current insurance information

• Employer coverage details

• Proof of qualifying events (marriage license, birth certificate, etc.)

Planning Ahead

Set Reminders:

• August: Start researching Medicare options

• September: Review employer benefits information

• October 1: Medicare preview materials available

• October 15: Medicare enrollment begins

• November 1: Marketplace enrollment opens

Annual Tasks:

• Update income estimates

• Review family healthcare usage

• Check if doctors/hospitals are in-network

• Verify prescription coverage

• Calculate total costs (not just premiums)

Get Help

Enrollment periods are stressful and confusing. Mistakes can be costly. We help you:

• Navigate all enrollment deadlines

• Compare plans accurately

• Understand subsidy eligibility

• Avoid coverage gaps

• Choose the right coverage for your needs

Don't wait until the last minute. Schedule a consultation early in the enrollment period for the best selection and peace of mind.