Tax Season 2026: 7 Things Tampa Bay Retirees Should Tell Their CPA

Tax season tends to arrive quickly, and for retirees in Tampa Bay, the window to act on certain strategies has already closed by April — but the conversation with your CPA does not have to be reactive. The difference between a good tax outcome and a great one often comes down to what your CPA knows before they start preparing your return. Most CPAs are excellent at compliance — getting the numbers right and filing on time. But they can only optimize what they know about, and retirement tax situations involve moving parts that may not appear on the documents your brokerage sends over.

Here are seven things worth bringing up before your return is finalized. Each one has the potential to affect your tax liability, your Medicare premiums, or both — and several of them interact with each other in ways that make the conversation worth having all at once rather than piecemeal.

1. Did you complete any Roth conversions last year? If you moved money from a traditional IRA to a Roth IRA in 2025, your CPA needs to know the amount and timing. Roth conversions create ordinary income, which affects your tax bracket, potential IRMAA surcharges, and whether additional estimated payments may have been due. A well-timed Roth conversion can save tens of thousands of dollars in future taxes, but a poorly communicated one can trigger unexpected penalties and premium increases that erase the benefit. Make sure your CPA has the 1099-R showing the conversion and understands whether it was part of a deliberate multi-year strategy.

2. Did you take required minimum distributions correctly? If you are 73 or older, your RMDs must be reported accurately. A missed or under-distributed RMD triggers a 25 percent excise tax on the shortfall — reduced to 10 percent if corrected promptly under the SECURE 2.0 Act provisions. Confirm the amounts with your CPA and verify each account was distributed properly. If you have multiple IRAs, the total RMD can be taken from any combination of them, but each 401(k) must satisfy its own RMD separately — a distinction that catches people off guard.

3. Did you make qualified charitable distributions? If you gave directly from your IRA to a qualifying charity, that amount is excluded from your taxable income under QCD rules — but only if reported correctly. QCDs are particularly valuable for Florida retirees who do not itemize deductions, since the state has no income tax and the standard deduction often wins. A QCD of $5,000 that is incorrectly reported as a normal distribution adds $5,000 to your adjusted gross income, which can trigger higher Medicare premiums and increased taxation of your Social Security benefits. The paperwork matters.

4. Will IRMAA affect your Medicare premiums in 2026? IRMAA — the Income-Related Monthly Adjustment Amount — is based on your income from two years prior. Your 2025 income determines your 2027 Medicare Part B and Part D premiums. If you had an unusual income event, such as a large Roth conversion, the sale of a business, or a significant capital gain, discuss whether a life-changing event appeal to Social Security is warranted. The IRMAA thresholds are not indexed to inflation, which means more retirees cross them each year even without dramatic income changes.

5. Were your estimated tax payments sufficient? Retirees without employer withholding often rely on quarterly estimated payments, and getting the amounts right is more art than science when income varies. If your income shifted in 2025 — from Social Security adjustments, pension changes, portfolio distributions, or investment gains — your CPA should review whether you owe an underpayment penalty and help recalibrate your quarterly payments for 2026. The safe harbor rule, which requires paying at least 100 percent of your prior year's tax liability (or 110 percent if your AGI exceeds $150,000), is worth confirming each year.

6. Did you sell any investments at a gain or loss? Capital gains from taxable brokerage accounts are taxed at different rates depending on how long assets were held. Short-term gains are taxed as ordinary income, while long-term gains benefit from preferential rates. If you had losses, confirm whether they were harvested to offset gains — and whether any wash sale rules apply. For retirees in lower brackets, the 0 percent long-term capital gains rate may apply to gains falling within the 10 or 12 percent ordinary income brackets, something worth planning around deliberately rather than discovering after the fact.

7. Is your tax withholding on Social Security optimized? Up to 85 percent of Social Security benefits may be taxable depending on your combined income — a figure that surprises many retirees who assumed their benefits would be received tax-free. You can elect voluntary federal withholding on your benefits using Form W-4V at rates of 7, 10, 12, or 22 percent, which simplifies estimated payment management and avoids underpayment penalties. For many Wesley Chapel and Tampa Bay retirees, choosing the right withholding rate on Social Security is one of the simplest ways to avoid an unpleasant surprise in April.

One broader point worth raising with your CPA: these seven items do not exist in isolation. A Roth conversion affects your IRMAA exposure. A QCD reduces your adjusted gross income, which affects how much of your Social Security is taxable. Capital gains push income higher, which can change your Medicare premiums two years from now. The value of a coordinated conversation — where all seven items are on the table at once — is that your CPA can see the full picture and make recommendations that account for how each piece affects the others.

At Protective Wealth Advisors, we work alongside CPAs serving Tampa Bay retirees to make sure tax planning is coordinated with your broader retirement income strategy. We often join client meetings with their CPA or provide a written summary of the year's planning activity so nothing falls through the cracks. Tax season is not the only time to think about taxes — but it is an important checkpoint, and the quality of the conversation you have now shapes the decisions you will make for the rest of the year.