Medicare Enrollment Resources
Everything you need in one place — official government links, enrollment period dates, penalty information, and plain-talk guides. No sign-up required.
Call (386) 871-3858 — Free GuidanceMedicare Enrollment Periods
Missing an enrollment window can result in permanent premium penalties. Know your dates.
Initial Enrollment Period (IEP)
People turning 65 or newly eligible for Medicare7-month window: 3 months before, the month of, and 3 months after your 65th birthday
Enroll in Part A, Part B, and choose a drug plan or Medicare Advantage plan
Annual Enrollment Period (AEP)
Anyone already on MedicareOctober 15 – December 7 (every year)
Switch plans, add/drop drug coverage, change between Original Medicare and Medicare Advantage
Medicare Advantage Open Enrollment (MA OEP)
People enrolled in a Medicare Advantage planJanuary 1 – March 31 (every year)
Switch Medicare Advantage plans or return to Original Medicare
General Enrollment Period (GEP)
People who missed their Initial Enrollment PeriodJanuary 1 – March 31 (every year)
Enroll in Part A and/or Part B (late penalties may apply)
Special Enrollment Period (SEP)
People who experience a qualifying life eventVaries by qualifying event (typically 2–8 months)
Enroll or make changes outside normal windows (losing employer coverage, moving, etc.)
Late Enrollment Penalties
These penalties are permanent — they follow you for the rest of your Medicare coverage.
Part B Late Penalty
10% added to your Part B premium for each full 12-month period you were eligible but did not enroll.
Example: If you delayed 2 years: your Part B premium increases by 20% — permanently.
Standard 2026 Part B premium: $202.90/month
Part D Late Penalty
1% of the national base beneficiary premium × the number of months without creditable drug coverage.
Example: If you went 24 months without drug coverage: ~$0.38 × 24 = ~$9.12/month added permanently.
2026 national base beneficiary premium: ~$38.00/month
Not sure if you owe a penalty?
Call me and I will calculate your exact situation — and help you minimize any penalties you may face.
Medicare Forms & Applications
Official government forms for Medicare enrollment, financial assistance, and proof of coverage — with plain-English explanations of when and how to use each one.
Medicare Income-Related Monthly Adjustment Amount — Life-Changing Event
If your Medicare Part B or Part D premium was increased due to IRMAA (Income-Related Monthly Adjustment Amount) and your income has since dropped because of a qualifying life-changing event, use SSA-44 to request that SSA use a more recent year's income instead of the two-year-old tax return they normally rely on.
What You'll Need
- Medicare number and Social Security number
- Proof of the life-changing event (marriage certificate, death certificate, retirement letter, etc.)
- Documentation of your reduced income (recent tax return, Social Security award letter, pension statement)
- The year of the life-changing event and the year you want SSA to use for income
William's Tip
IRMAA is based on your tax return from two years prior. If a qualifying event reduced your income after that return was filed, SSA-44 lets you appeal. Qualifying events include: marriage, divorce, death of a spouse, work stoppage or retirement, loss of income-producing property, loss of pension income, and employer settlement payments. Investment losses, capital gains, voluntary income reduction, and general financial hardship do NOT qualify. Call William — he can walk you through whether your situation qualifies before you file.
Call (386) 871-3858 for helpApplication for Extra Help with Medicare Prescription Drug Plan Costs
The Extra Help (Low Income Subsidy / LIS) program helps people with limited income and resources pay for Medicare Part D prescription drug costs — including premiums, deductibles, and copays. You may qualify if your annual income is below ~$22,590 (individual) or ~$30,660 (married couple) in 2026.
What You'll Need
- Social Security number
- Information about income (wages, Social Security, pension, etc.)
- Information about resources (bank accounts, stocks, bonds, real estate other than your home)
William's Tip
You can also apply online at SSA.gov or call 1-800-772-1213. William can help you determine if you qualify before you apply.
Call (386) 871-3858 for helpFlorida Medicaid Application (ACCESS Florida)
Florida Medicaid provides health coverage for low-income individuals and families. If you qualify for both Medicare and Medicaid, you are considered "dual eligible" — which can dramatically reduce or eliminate your Medicare premiums, deductibles, and cost-sharing. Florida Medicaid applications are submitted through the ACCESS Florida portal.
What You'll Need
- Proof of identity (driver's license, state ID, or passport)
- Proof of Florida residency
- Social Security number
- Proof of income (pay stubs, Social Security award letter, pension statements)
- Proof of assets (bank statements, property records)
William's Tip
Florida Medicaid is applied for online through ACCESS Florida — there is no single PDF form. William can walk you through the process and explain how dual eligibility affects your Medicare plan options.
Call (386) 871-3858 for helpApplication for Enrollment in Medicare — Part B (Medical Insurance)
Use this form to enroll in Medicare Part B (Medical Insurance) if you are already enrolled in Part A, or if you are applying during a Special Enrollment Period (SEP) after losing employer coverage. This form is submitted to your local Social Security office.
What You'll Need
- Medicare number (from your red, white, and blue Medicare card)
- Date your current health insurance coverage began (if applying during SEP)
- Name and address of your employer or union (if applicable)
William's Tip
If you are enrolling during a Special Enrollment Period due to losing employer coverage, you must submit CMS-40B together with Form L564 (below). Submit both to your local Social Security office.
Call (386) 871-3858 for helpRequest for Employment Information — Proof of Group Health Plan Coverage
Form L564 is completed by your employer (or former employer) to verify that you had employer-sponsored group health plan coverage. This form is required when you apply for Medicare Part B during a Special Enrollment Period (SEP) — it proves you had creditable coverage and are not subject to a late enrollment penalty.
What You'll Need
- Your name, address, and Medicare number
- Your employer's name, address, and contact information
- Dates of employment and group health plan coverage
- Employer's signature and date
William's Tip
Have your employer complete Section B of this form. Then submit it along with your CMS-40B Part B application to your local Social Security office. Keep a copy for your records.
Call (386) 871-3858 for helpNot sure which form you need?
Call William and he will tell you exactly which forms apply to your situation — and walk you through completing them correctly.
Official Government Resources
Direct links to official Medicare and Social Security resources — no middleman.
Schedule a Free Enrollment Appointment
Book a free one-on-one appointment with William Gray. He'll compare every plan in your ZIP code against your doctors and medications — no pressure, no cost.
Book My Free AppointmentMedicare.gov
Official U.S. Medicare website. Compare plans, check coverage, view claims, and manage your Medicare account.
Visit Medicare.govMedicare Plan Finder
Compare Medicare Advantage, Part D drug plans, and Medigap policies available in your ZIP code.
Compare PlansSocial Security Administration
Enroll in Medicare Part A and Part B, apply for Social Security benefits, and manage your account.
Visit SSA.govExtra Help (Low Income Subsidy)
Apply for the Extra Help program to reduce your Medicare Part D prescription drug costs.
Apply for Extra HelpMedicare & You Handbook
The official annual Medicare handbook. Download the current year edition in English or Spanish.
Download HandbookState Health Insurance Assistance Program (SHIP)
Free, unbiased Medicare counseling from trained volunteers in your state.
Find Local SHIPFree Medicare Guides
Plain-talk articles written by William Gray — no jargon, no sales pitch.
Have Questions? I Am Here to Help.
Call me at (386) 871-3858 for free, unbiased Medicare guidance — no pressure, no obligation.
We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov or 1-800-MEDICARE (TTY: 1-877-486-2048) to get information on all of your options.
Not affiliated with or endorsed by the U.S. government or the federal Medicare program. This is an advertisement for insurance. William Gray and affiliated licensed agents are independent insurance agents, not government employees or representatives. Medicare has neither reviewed nor endorsed this information.
Not all plans or types of coverage may be available in your area. Plan availability, benefits, and premiums vary by county and ZIP code. Enrollment in any plan depends on contract renewal. Benefits, premiums, and cost-sharing may change on January 1 of each year.
Independent Agent & Compensation Disclosure. William Gray is an independent licensed insurance agent (FL License #W690237) and is not employed by or exclusively affiliated with any single insurance company. William is compensated by insurance carriers when you enroll in a plan. This compensation does not affect the premium you pay — your premium is the same whether you enroll through a broker or directly with the carrier. Affiliated agents are independent contractors solely responsible for their own conduct and representations.