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Enrollment deadlines, decoded.

Get expert assistance with enrollment periods, important deadlines, and step-by-step guidance for all your insurance needs — health Marketplace, Medicare, Medicaid & CHIP. Miss a window and it can cost you for years. We make sure you never do.

Health Open EnrollmentNov 1 – Jan 15 Medicare Open EnrollmentOct 15 – Dec 7 Medicare Initial Enrollment7 months around your 65th birthday
Health insurance enrollment periods

When can you actually enroll?

Marketplace health coverage runs on a calendar — but life events open extra doors, and some programs never close. Here's every window, in plain English.

Open Enrollment Period

November 1 – January 15

The annual period when anyone can enroll in or change Marketplace health insurance plans for the following year. No qualifying event needed — just don't miss it.

Special Enrollment Period

60 days after a qualifying event

Available after life changes like marriage, job loss, moving, or having a baby.

Qualifying events:

  • Loss of health coverage (job loss, divorce)
  • Changes in household (marriage, birth, adoption)
  • Changes in residence (moving to a new area)
  • Changes in income (affects subsidy eligibility)

Medicaid / CHIP Enrollment

Year-round

You can apply for Medicaid and CHIP any time of year. If you qualify, coverage can start immediately — no waiting for an enrollment window.

Medicare enrollment periods

Medicare runs on its own clock.

Four different windows, four different rules — and missing the first one can mean late-enrollment penalties for life. Here's the map.

IEP · Don't miss this one

Initial Enrollment Period

3 months before to 3 months after turning 65

Your first chance to enroll in Medicare — a 7-month window around your 65th birthday. Missing this deadline can result in late enrollment penalties that follow you permanently.

AEP · Annual switch window

Annual Open Enrollment

October 15 – December 7

Change Medicare Advantage or Part D plans, or switch between Original Medicare and Medicare Advantage for the coming year.

MA OEP · The do-over

Medicare Advantage Open Enrollment

January 1 – March 31

If you're in a Medicare Advantage plan, you can switch to another MA plan or return to Original Medicare — one change, once a year.

SEP · Life happens

Special Enrollment Periods

Various triggers throughout the year

Moving, losing coverage, or qualifying for Extra Help can trigger special enrollment opportunities outside the standard windows.

Not sure which window applies to you? That's exactly what a free call is for — we'll check your dates, your plan, and your penalty exposure in minutes.

The enrollment process

Five steps from confused
to covered.

Enrollment isn't complicated when someone walks you through it. Here's the exact process we follow with every client — and the paperwork to have on hand.

  1. Assess your needs

    Review your current health, medications, and preferred doctors to determine what coverage you actually need.

  2. Compare plans

    Look at premiums, deductibles, networks, and covered services to find the best value for your situation — not just the lowest sticker price.

  3. Gather documents

    Collect your Social Security number, tax returns, employer coverage information, and current insurance details.

  4. Complete the application

    Submit your enrollment application online, by phone, or with the help of a licensed agent — we handle the forms with you.

  5. Confirm coverage

    Receive confirmation and ID cards, then pay your first premium to activate coverage. We double-check that everything went through.

Have ready
iCoach Solutions
Required Documents Checklist
📋 Social Security card
💰 Tax return or income info
🏢 Employer coverage details
💳 Current insurance cards
💊 Prescription drug list
🏥 Preferred doctor information

Bring these to your call & we can often finish enrollment same-day.

Common enrollment mistakes to avoid

What costs people money —
and what saves it.

After thousands of enrollments, the same handful of mistakes shows up again and again. Here's the cheat sheet.

⚠️ Costly mistakes

  • Missing enrollment deadlines
  • Not checking provider networks
  • Ignoring prescription coverage
  • Choosing based on premium only
  • Not updating after life changes

✅ Smart strategies

  • Start shopping early
  • Calculate total annual costs
  • Verify doctor participation
  • Review plan changes annually
  • Work with licensed experts
Why use an agent?

Don't navigate enrollment alone.

Our licensed experts will guide you through every step of the process — and it never costs you a dime more than enrolling on your own.

No cost for our services

You pay nothing for our help — agent assistance is built into the system, with zero markup on your premium.

🧠

Expert knowledge of all options

We compare across carriers and plan types, not just one company's lineup.

Help with applications & enrollment

We complete the paperwork with you and make sure it's submitted correctly the first time.

Ongoing support & advocacy

Claims questions, plan changes, life events — we stay in your corner long after enrollment day.

Navigate complex rules & deadlines

SEPs, IEPs, penalties, exceptions — we track the rules so you never get caught out.

30 years in the financial & healthcare industries

Three decades of industry knowledge, applied to your enrollment by licensed agents.

Get enrollment help

Your deadline is coming.
Let's beat it together.

Free, no-pressure enrollment assistance from licensed professionals. We'll check your windows, compare your options, and walk you through every step.