Important Disclaimer: HTG Advisors is not a Medicare expert, and we rely on specialized Medicare professionals to advise our clients on a case-by-case basis. However, from our experience working with clients through healthcare transitions and retirement planning, we have learned valuable insights that we share below.
Enrolling in Medicare can feel overwhelming, but understanding the process and key components like the Income-Related Monthly Adjustment Amount (IRMAA) can help you make informed decisions about your healthcare coverage. Working with a financial advisor during this transition adds significant value, as we help clients understand how Medicare decisions impact their broader retirement strategy and coordinate timing with benefits like HSAs and employer coverage. From our experience, having professional guidance proves invaluable when navigating the complex intersection of healthcare costs, tax implications, and retirement planning.
This 2025 Medicare enrollment guide walks you through the basics about Medicare enrollment, including how to appeal if your income has decreased, plus shares practical insights we’ve gained from helping clients avoid common pitfalls during their Medicare transitions.
Understanding Medicare Enrollment Periods: When You Can Sign Up
Medicare enrollment isn’t a one-size-fits-all process. There are several enrollment periods to be aware of:
Initial Enrollment Period (IEP)
This seven-month window begins three months before your 65th birthday, includes your birthday month, and extends three months after. If you’re already receiving Social Security benefits, you’ll be automatically enrolled in Medicare Parts A and B.
General Enrollment Period: Second Chance Sign-up
If you miss your IEP, you can enroll during the General Enrollment Period from January 1 to March 31 each year, with coverage beginning July 1. However, you may face late enrollment penalties.
Special Enrollment Periods: Life Event Triggers
These allow you to enroll outside of the initial or general enrollment periods and occur when you experience qualifying life events, such as losing employer-sponsored health coverage (including retirement), moving outside your plan’s service area, or qualifying for Extra Help with prescription drug costs.
Open Enrollment Period: Annual Plan Changes
From October 15 to December 7 annually, you can change your Medicare health or prescription drug plans.
How to Enroll in Medicare
Automatic Medicare Enrollment
For people turning 65 who are already receiving Social Security, the enrollment process begins automatically. You’ll receive your Medicare card in the mail about three months before your 65th birthday.
Manual Medicare Enrollment
If you’re not receiving Social Security, you’ll need to actively enroll by contacting Social Security or visiting their website.
When enrolling, you’ll need to make several key decisions:
- Medicare Part A (hospital insurance): Premium-free for most people
- Medicare Part B (medical insurance): Requires monthly premiums
- Medicare Supplement (Medigap) policy: Additional coverage option
- Part D prescription drug plan: Standalone drug coverage
- Medicare Advantage plans: An alternative that typically includes prescription coverage
Understanding IRMAA: Income-Related Monthly Adjustment Amount Explained
One crucial aspect many new Medicare beneficiaries don’t anticipate is IRMAA – the Income-Related Monthly Adjustment Amount. This additional premium applies to Medicare Parts B and D for higher-income beneficiaries and is based on your modified adjusted gross income (MAGI) from two years prior.
For 2025, IRMAA kicks in when your MAGI exceeds:
- $106,000 for individuals or
- $212,000 for married couples filing jointly (based on 2023 tax returns).
The additional premiums are substantial and increase in tiers. For example, couples with income between $212,000 and $266,000 each pay an additional $74 per month for Part B, while those with income over $750,000 pay an additional $443.90 per month per person.
IRMAA also applies to Part D prescription drug coverage, with additional monthly amounts ranging from $13.70 to $85.50 depending on your income level. These adjustments are automatically calculated by Social Security using tax information from the IRS, and you’ll receive a notice if you’re subject to IRMAA.
How to Appeal IRMAA Due to Reduced Income
If your income has significantly decreased since the tax year used to calculate your IRMAA, you may be eligible to appeal and potentially reduce or eliminate these additional premiums. This is particularly important for recent retirees whose current income is much lower than their pre-retirement earnings.
Qualifying Life-Changing Events
Social Security recognizes several life-changing events that may justify an IRMAA appeal:
- Work reduction or retirement by you or your spouse
- Loss of pension income
- Loss of income-producing property due to disaster or other circumstances
- Divorce or annulment
- Death of spouse
- Marriage
The Appeal Process
To request an IRMAA reconsideration, you’ll need to:
- Complete Form SSA-44 (Medicare Income-Related Monthly Adjustment Amount – Life-Changing Event)
- Provide documentation supporting your reduced income. This might include recent tax returns, pay stubs, pension statements, or other financial documents.
- Submit your appeal online through your mySocialSecurity account, by phone, mail, or in person at your local Social Security office.
- File promptly. You generally have 60 days from receiving your IRMAA notice, though Social Security may accept late appeals in certain circumstances.
If you are married filing jointly, both spouses will need to submit an appeal to have their IRMAA reconsidered.
What to Expect
Social Security will review your appeal and supporting documentation. If approved, they’ll adjust your IRMAA based on your current income situation, and any overpaid premiums may be refunded. The decision process typically takes 30-60 days, though complex cases may take longer.
Common Medicare Enrollment Pitfalls We’ve Observed
Through our work with clients, we’ve identified several common mistakes that can be costly:
COBRA and Medicare Timing Issues
One critical consideration we frequently encounter is the interaction between COBRA coverage and Medicare enrollment. COBRA is generally not considered creditable coverage for Medicare Parts A and B, and individuals who choose COBRA instead of enrolling in Medicare on time may face permanent late enrollment penalties.
HSA Considerations and Critical Timing
For clients with Health Savings Accounts (HSAs), we’ve learned several important rules that can be costly if overlooked. After age 65, HSA funds can be used to pay for Medicare Part B, Part D, Medicare Advantage, and long-term care premiums, which can be a valuable strategy for managing Medicare costs in retirement.
However, there’s a critical timing issue we frequently help clients navigate: you must stop HSA contributions at least 6 months before enrolling in Medicare to avoid penalties and potential tax issues. This timing requirement exists because Medicare Part A coverage is retroactive for up to 6 months when you enroll, and you cannot contribute to an HSA while enrolled in Medicare.
Automatic Medicare Enrollment Warning
If you’re already collecting Social Security benefits when you turn 65, you will be automatically enrolled in Medicare Parts A and B. This creates a particular challenge for HSA contributors because the automatic enrollment means you may unknowingly become ineligible to contribute to your HSA. We always advise clients who are collecting Social Security and contributing to HSAs to plan for this transition carefully.
State-to-State Moves
We’ve seen clients face unexpected challenges when relocating after Medicare enrollment. Moving to a different state triggers a special enrollment period, particularly important for Medicare Advantage, Medicare Part D, and supplemental coverage, which may have different networks and benefits across state lines.
Our Approach: Partnering with Medicare Specialists
At HTG Advisors, we recognize that Medicare planning is highly specialized and individual circumstances vary greatly. Rather than trying to be Medicare experts ourselves, we maintain a network of trusted Medicare professionals who can provide detailed, case-specific guidance to our clients.
We include Medicare decisions within clients’ retirement planning services to help them understand how Medicare fits into their overall financial plan, particularly regarding:
- Income planning strategies that may impact IRMAA
- Coordination with existing healthcare benefits during employment transitions
- Integration of Medicare costs into retirement budgeting
- HSA utilization strategies for Medicare premiums
Planning Ahead
Understanding Medicare enrollment and IRMAA implications is crucial for retirement planning. From our experience, we strongly recommend clients begin Medicare planning conversations at least 6 months before their 65th birthday or retirement, whichever comes first.
If you’re approaching Medicare eligibility, consider working with both a financial advisor to understand the broader retirement implications and a specialized Medicare professional who can guide you through the specific enrollment decisions and plan comparisons.
Remember that Medicare rules and premium amounts change annually, so staying informed about updates is essential. The Medicare and Social Security Administration websites both provide current information and tools to help you navigate your options effectively.
By understanding these processes upfront and working with qualified professionals, you can make informed decisions about your Medicare coverage and take appropriate action if your financial circumstances change.