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. Here are seven things worth bringing up before your return is finalized.

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.

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 quickly. Confirm the amounts with your CPA and verify each account was distributed properly.

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.

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 premiums. If you had an unusual income event, such as a large Roth conversion or asset sale, discuss whether a life-changing event appeal to Social Security is warranted.

5. Were your estimated tax payments sufficient? Retirees without withholding often rely on quarterly estimated payments. If your income shifted in 2025 — from Social Security, pensions, distributions, or investment gains — your CPA should review whether you owe a penalty and help recalibrate payments for 2026.

6. Did you sell any investments at a gain or loss? Capital gains from taxable brokerage accounts are taxable at different rates depending on how long assets were held. If you had losses, confirm whether they were harvested to offset gains. For retirees in lower brackets, the 0 percent long-term capital gains rate may apply — something worth planning around.

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. Many retirees are surprised to learn this. You can elect voluntary withholding on your benefits using Form W-4V, which simplifies estimated payment management and avoids underpayment penalties.

At The Protective Wealth Group, we work alongside CPAs serving Tampa Bay retirees to make sure tax planning is coordinated with your broader retirement income strategy. Tax season is not the only time to think about taxes — but it is an important checkpoint.