Medicare Guide for CPAs and Financial Advisors

Who this guide is for

We built this guide for CPAs, enrolled agents, financial advisors and other professionals helping Utah clients approach Medicare or retire after enrolling. Clients and families can use it too.

We explain Medicare enrollment and coverage. The client’s CPA or tax professional should calculate income, assess deductions and recommend tax strategies. Social Security determines IRMAA and Medicare enrollment eligibility. This guide does not replace its decision or provide tax or legal advice.

IRMAA: the income lookback and SSA-44

The income-related monthly adjustment amount (IRMAA) can add to Part B and Part D costs. Social Security generally uses the tax return from 2 years before the coverage year. For Medicare IRMAA, modified adjusted gross income (MAGI) is adjusted gross income plus tax-exempt interest. If the usual return is unavailable, SSA may use the prior return instead. (SSA: Medicare premiums for higher-income beneficiaries)

A client who retires, reduces work or experiences another qualifying event may ask SSA to use more recent, lower income. Form SSA-44 requests a new determination after a qualifying life-changing event; formal reconsideration is a different process. A Roth conversion or property sale alone does not qualify. (SSA: request to lower IRMAA) (SSA POMS HI 01120.005: life-changing events)

Use our SSA-44 and IRMAA appeal guide for events and documents. For annual tables and an estimate tool, use our IRMAA brackets and calculator page. Annual figures update each fall; confirm the applicable year with CMS and SSA rather than treating projections as released amounts. We do not state 2027 dollar figures here.

HSA stop timing: confirm the Part A start date

Enrolling in any part of Medicare ends HSA contribution eligibility for covered months. That affects amounts from the client, payroll and employer. Part A alone matters; delaying Part B does not preserve HSA eligibility after Part A starts. (IRS Publication 969: Health Savings Accounts)

When a client delays Part A beyond age 65, Part A with no premium can start up to 6 months before the application for Medicare or Social Security benefits, but not before the age-based eligibility month. For a delayed application, plan to stop HSA contributions at least 6 months before applying and confirm the effective date with SSA. This is not a blanket instruction to stop 6 months before every client’s 65th birthday. (Medicare.gov: when Medicare coverage starts) (Medicare.gov: working past 65)

The tax professional should confirm the eligible-month limit and contribution-year allocation, including employer amounts and any excess correction. See our Medicare and HSA guide for the timing table and permitted uses of existing funds.

Still working at 65: separate medical and drug coverage questions

We ask whether coverage comes from the client’s or spouse’s current employment, which plan pays first, and whether drug coverage is creditable. For age-based Medicare, the employer-size threshold of 20 employees generally affects which plan pays first. Multi-employer arrangements and other eligibility situations can differ. Confirm the answer with the benefits administrator. (Medicare.gov: who pays first) (Medicare.gov: working past 65)

The employment-based Part B Special Enrollment Period generally ends 8 months after employment or group coverage ends, whichever happens first. COBRA does not extend it. Clients adding Part B may use CMS-40B and CMS-L564; SSA also describes an online route. (Medicare.gov: when Medicare coverage starts) (SSA: sign up for Part B only)

Coordinate Medicare and job-coverage dates with HR before setting dates. A spouse staying on the employer plan may need a separate coverage discussion.

Part B and Part D late enrollment penalties

The penalties use different rules and bases. They are separate from an income-related adjustment. Our calculator illustrates scenarios, not a coverage or penalty determination. (Medicare.gov: late enrollment penalties)

On a phone, scroll the table sideways to read both columns.

Source: Medicare.gov penalty rules. The embedded calculator uses labeled 2026 Medicare program amounts for illustration; it does not quote a plan premium or determine what you owe.

Open the combined Part B and Part D penalty calculator. Both tools are on that page.

When to refer a client to a licensed Medicare agent

A phone conversation can help when a client needs to coordinate a retirement date, compare coverage paths, check doctors and prescriptions, or identify enrollment questions for SSA or HR. We can explain Medicare choices while the client’s tax professional handles income projections and HSA tax reporting.

For an IRMAA decision or reconsideration, the client submits information to SSA. We do not decide eligibility or promise a reduction. Please have the client call rather than emailing tax returns, Social Security numbers or health records.

Printable client-handoff checklist

This is a conversation aid, not an application or tax recommendation. Keep private notes in your own secure client file.

• Confirm retirement, job-coverage end dates and Part A/Part B effective dates with the relevant agencies and HR.
• Ask HR which plan pays first and whether drug coverage is creditable. Keep the written coverage notice.
• Have the tax professional check retroactive Part A months, employee/employer HSA amounts and the allowable contribution-year total.
• Compare SSA’s income year with current circumstances. Ask whether a qualifying event supports an SSA-44 request.
• Have the client prepare questions about doctors, prescriptions and coverage preferences for a licensed agent. Do not put private records on this handout.
• Give the client our phone number and guide link. SSA handles enrollment and IRMAA decisions; the tax professional handles tax advice.

Print this checklist

Rule references: IRS Publication 969; Medicare.gov coverage-start rules; SSA guidance on lowering IRMAA. Full source links are on the web guide.

Read the linked references at booinsuranceservices.com/medicare-guide-for-financial-advisors/
No cost to talk with us.

Questions we hear

Is this guide only for financial advisors?

No. We wrote it for CPAs, enrolled agents, financial advisors and other professionals, but clients and families can use it too. It is Medicare education, not tax or legal advice.

Where are the Part B and Part D penalty calculators?

Both are on our combined Medicare penalty calculator page. They illustrate enrollment scenarios; Medicare or the plan determines any actual penalty.

Can retirement support an SSA-44 request?

Work stoppage or work reduction can qualify when it causes an income reduction that decreases or eliminates IRMAA. SSA reviews the evidence and makes the decision. A property sale or Roth conversion by itself is not a qualifying event.

How should a client contact our Medicare team?

Have the client call 801-255-5341, Mon–Fri 9am–5pm MT, TTY 711. No cost to talk with us. Tax returns and private medical records are not needed to request a phone conversation.

Sources and rule references

References checked November 6, 2026 (MT). Use the current agency instructions for a personal decision.

1. SSA: Medicare premiums for higher-income beneficiaries
2. SSA: request to lower IRMAA
3. SSA POMS HI 01120.005: life-changing events
4. SSA POMS HI 01140.001: IRMAA appeal process
5. IRS Publication 969: Health Savings Accounts
6. Medicare.gov: when Medicare coverage starts
7. Medicare.gov: working past 65
8. Medicare.gov: who pays first
9. SSA: sign up for Part B only
10. Medicare.gov: late enrollment penalties
11. CMS: 2026 Medicare Parts A & B premiums and deductibles
12. Medicare.gov: contact Medicare