Essential Financial Dates for Retirees in 2025

For retirees, keeping track of key financial dates can help with managing important tasks like tax filings, healthcare decisions, and retirement account distributions. This list of 2025 milestones highlights notable deadlines that could impact your financial planning. Whether it’s reviewing your estate plan, addressing required minimum distributions (RMDs), or exploring healthcare options, being aware of these dates may support your efforts to stay organized and make timely decisions. Here’s a rundown of the essential dates to consider as you prepare for the year ahead: 

Feb. 15* 

Are you 59½ or older and still working? You may be able to elect an in-service rollover of your 401(k) or TSP to an IRA and prepare for retirement. 

March 31 

General enrollment for traditional Medicare ends, and open enrollment for Medicare Advantage ends. (Window opens Jan. 1.)  

April 1 

Normally the date by which those attaining RMD starting age (73) would have to take their first RMD. However, due to provisions in the Secure Act 2.0, if you reached age 72 in 2024, then your first RMD for 2025 (the year you will turn 73) will be due by April 1, 2026. 

May 15* 

Risk Review. Optimal time to review your investment balance and stress test for hidden risks. 

April 15 

1. 2024 taxes are due
2. Last chance to make contributions to an IRA
3. First quarter estimated tax payment for 2025 

June 16 

Second quarter estimated taxes are due. 

Aug. 1* 

Estate tune-up. Is your estate plan up to date? Do you have proof that each asset you own has beneficiaries (bank, insurance, IRAs, etc.)?  

Sept. 15 

Third quarter tax estimate for 2025 is due (you could catch up by withholding taxes from your RMD).

Sept. 30 

By this date, you will have received Medicare’s annual notice of changes for either Medicare Advantage or Part D. Changes take place in 2026. 

Oct. 15 

Medicare open enrollment begins, with coverage beginning in 2026. 

Oct. 15 

Tax deadline for individuals who filed an extension. 

Nov. 1 

Early retirees can buy health insurance on the ACA exchange, with coverage beginning in 2026. 

Dec. 1 

Begin QCD (qualified charitable distribution) process so the charity can receive the money in time (ages 70½+ can give up to $108K).  

Dec. 3* 

Review your YTD investment gains and losses, complete year-end tax planning (deduction bunching, gifting, harvesting losses, etc.). 

Dec. 7 

Medicare open enrollment ends. 

Dec. 15 

1. ACA open enrollment ends for those who want coverage to be effective as of Jan. 1, 2026. (Enrollment continues through Jan. 15, 2026, with later enrollments electing coverage effective Feb. 1, 2026.) 
2. Roth conversions should be done by now to ensure completion before year-end.

Dec. 31 

Happy New Year! Did you take your RMD yet? Any last-minute gifting you want to do? Did you take your RMD yet? Have you started to think about your financial and retirement goals for 2025? 
 

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Conclusion

Managing financial deadlines as a retiree can be a complex process, but having a clear view of key dates may help streamline your planning. By referring to this list and staying informed, you can approach tax filings, investments, and healthcare decisions with greater clarity. If you have questions about how these dates might apply to your situation, consider reaching out to a financial professional for guidance tailored to your circumstances. We invite you to book an appointment with our team to discuss your unique goals and explore strategies that align with your retirement plans. Taking steps to stay prepared throughout the year could help make the financial aspects of retirement more manageable. 

 

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