Deorbit Plan

Retirement deadlines calendar (2026–2027)

Tax, RMD, Medicare and Marketplace dates for retirees, with a calendar file to keep

By the Deorbit Plan editorial team, a Berrydyne program · Last reviewed · Topic: Taxes in retirement

What it computes

One list of the dates a retiree’s year runs on: the four estimated-tax payments[7], the return and extension due dates[8], the last day for prior-year IRA[9] and HSA[10] contributions, December 31 for RMDs, Roth conversions and qualified charitable distributions[12], Medicare’s enrollment windows[13][14] and HealthCare.gov Open Enrollment[15]. Each date links to the guide that explains it.

Add a birth month and year and the calendar merges in your own dates: the month you reach 59½, your seven-month Medicare Initial Enrollment Period, full retirement age, 70, 70½, and your first two RMD deadlines[11]. Download the result as a calendar file; it is built in your browser and nothing you type is saved or sent.

Retirement deadlines calendar

Optional: add birth months and years to merge your own milestones (59½, Medicare sign-up, Social Security ages, first RMDs) into the list. They stay on this page; nothing is saved or sent.

You
Spouse or partner (optional)

2026: 16 dates

  • Medicare Advantage Open Enrollment Already in a Medicare Advantage plan? You can make one change: switch plans, or return to Original Medicare and join a drug plan. Read the rule
  • Medicare General Enrollment Period If you missed your Initial Enrollment Period and have no Special Enrollment Period, this is when you can sign up for Part B; coverage starts the month after you sign up, and a late-enrollment penalty may apply. Read the rule
  • Estimated tax: fourth 2025 payment due Covers income received September 1 – December 31 2025, if your withholding does not already cover the year's tax. Read the rule
  • Estimated tax: first 2026 payment due Covers income received January 1 – March 31, if your withholding does not already cover the year's tax. Read the rule
  • Last day for 2025 HSA contributions HSA contributions for 2025 can be made until the return's due date without extensions, for the months you were eligible (not after Medicare starts). Read the rule
  • Last day for 2025 IRA contributions Traditional and Roth IRA contributions for 2025 can be made until the return's due date, not including extensions. Tell the custodian which year a contribution is for. Read the rule
  • 2025 federal tax return due (or file for an extension) Form 1040 for 2025, and any tax still owed, is due. An extension (Form 4868) gives six more months to file but not to pay. Read the rule
  • Estimated tax: second 2026 payment due Covers income received April 1 – May 31, if your withholding does not already cover the year's tax. Read the rule
  • Estimated tax: third 2026 payment due Covers income received June 1 – August 31, if your withholding does not already cover the year's tax. Read the rule
  • Extended 2025 tax return due If you filed for an extension, the 2025 return is due. Interest on unpaid tax has run since April. Read the rule
  • Medicare Open Enrollment for 2027 coverage Join, switch or drop a Medicare Advantage or drug plan; changes start January 1, 2027. The plan must get your request by December 7. Read the rule
  • HealthCare.gov Open Enrollment for 2027 coverage Enroll in or change a Marketplace plan for 2027. States that run their own Marketplace may use other dates. Read the rule
  • Marketplace: last day to enroll for January 1, 2027 coverage Plans picked after this date, through January 15, 2027, start February 1. Read the rule
  • Last day for a 2026 qualified charitable distribution A QCD counts toward the year's RMD and is left out of income only in the year it is paid out of the IRA, so it must reach the charity by December 31. Read the rule
  • 2026 required minimum distributions due Every RMD for 2026 must be out of the account by December 31, except a first RMD that can wait until April 1. Custodians often need the request days or weeks earlier. Read the rule
  • Last day for a Roth conversion to count in 2026 A conversion is income in the year the money leaves the traditional IRA, so a 2026 conversion must be completed by December 31. There is no April deadline for conversions. Read the rule
Download the calendar (.ics)

The calendar file covers 2026 and 2027. To have new years appear on their own, add it to your calendar app by its address (“subscribe” or “add from URL”): https://deorbitplan.com/calendar/retirement-deadlines.ics. If your birthday is on the 1st of a month, Social Security and Medicare treat you as reaching each age a month earlier.

Worked example

The general calendar holds 16 in 2026 and 15 in 2027. None of the 2026 or 2027 tax dates falls on a weekend or holiday. When one does, the deadline moves to the next business day: a tax act due on a Saturday, Sunday or District of Columbia legal holiday is on time the next day that is none of those[8]. The next estimated-tax date it moves is January 15, 2028: January 15 is a Saturday; January 16 is a Sunday; January 17 is Birthday of Martin Luther King, Jr., a legal holiday, so the deadline moves to Tuesday, January 18, 2028.

Someone born in March 1962 reaches 75 in 2037, the start age for anyone born in 1960 or later[11], so their dates are:

Dates for someone born in March 1962
WhenWhat
December 1, 2026 – June 30, 2027Medicare Initial Enrollment Period
March 2029Reach full retirement age (67)
March 2032Reach 70: delayed retirement credits stop
September 2032Reach 70½: qualified charitable distributions allowed
Thursday, April 1, 2038First RMD (for 2037) due
Friday, December 31, 2038Second RMD (for 2038) due

The first RMD can wait until Thursday, April 1, 2038, but the second is then due the same year, which puts two RMDs into one tax year.

What it ignores

  • Disaster relief: the IRS often postpones deadlines for people in a federally declared disaster area. Those postponements are announced case by case and are not in this calendar.
  • Statewide legal holidays, which can move a filing date for residents of that state[8], and every state tax deadline.
  • Custodian cut-offs. RMDs, conversions and QCDs are dated by when the money leaves the account, and no weekend rule is published for them; many custodians need instructions days or weeks before December 31.
  • Marketplace dates for plan years HealthCare.gov has not yet published, and the different dates of states that run their own Marketplace.
  • Special Enrollment Periods (Medicare and Marketplace), the still-working exception that delays RMDs from a current employer’s plan, inherited-account deadlines, and fiscal-year, farming and fishing estimated-tax rules.
  • Your exact birthday: personal dates are shown by month. A birthday on the 1st moves Social Security and Medicare ages a month earlier.

The rule behind it

The full explanation, with sources, is in Safe-harbor rules: estimated taxes in retirement without penalties.

See it over a full plan

In the simulator, RMDs, Medicare from 65 and the Roth conversions you plan land in the right years automatically, so you can see what each deadline is worth over a full plan. Open it in the simulator →

If you already have a saved plan, the link only takes you to the right panel; your plan is not changed.

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This tool shows how the rules work. It is not financial, tax or investment advice. See the disclaimer.

Sources