Wealthy Pot

2027 Money Deadlines: Tax, Medicare, RMD and Enrollment Dates

Every federal money deadline for 2027 that you can act on, in date order: taxes, retirement accounts, Medicare, health insurance, federal benefits and student aid. Each date links to the official source. 25 of the 31 dates are already official; the rest are marked expected until the agency publishes them.

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Only the dates for you

January 2027

  1. Jan 1–Mar 31

    Medicare Advantage Open Enrollment Period

    If you are in a Medicare Advantage plan, you can switch to another Advantage plan or drop back to Original Medicare (and add a Part D plan) once between January 1 and March 31.

    Our guide · Source

  2. Jan 1–Mar 31

    Medicare General Enrollment Period

    If you missed your Initial Enrollment Period and have no Special Enrollment Period, sign up for Part B (or premium Part A) by March 31. Coverage starts the month after you sign up, and a late-enrollment penalty may apply.

    Our guide · Source

  3. Jan 1Fri

    New 2027 401(k), TSP and IRA limits take effect

    The inflation-adjusted 2027 limits for 401(k), 403(b), 457(b), TSP and IRA contributions apply from the first paycheck of 2027. Raise your contribution percentage if you want to save the new maximum; the IRS publishes the figures in a notice each fall.

    Our guide · Source

  4. Jan 15Fri

    Last day of ACA Marketplace Open Enrollment for 2027

    Last day to pick or change a HealthCare.gov plan for 2027 (plans picked December 16 to January 15 start February 1). After this you need a Special Enrollment Period; some state exchanges use other end dates.

    Our guide · Source

  5. Jan 15Fri

    4th-quarter 2026 estimated tax payment due

    Pay the last 2026 estimated tax installment if withholding does not cover your tax. You can skip it if you file your 2026 return and pay the full balance by February 1, 2027; otherwise a late or short payment adds an underpayment penalty.

    Our guide · Source

  6. Jan 18–Jan 31

    IRS starts accepting 2026 tax returns (date TBA) expected

    The IRS opens e-filing for 2026 returns in late January and announces the exact day in early January. Filing early with direct deposit gets refunds fastest; nothing is due on this date.

    Our guide · Source · basis: Not yet announced. Pattern: the 2026 season opened Monday, January 26, 2026 (IR-2026-02, announced Jan 8, 2026). Window shown is our estimate, not an IRS date.

February 2027

  1. Feb 1Mon

    W-2 and 1099-NEC forms due to workers

    Employers must give you your 2026 Form W-2, and clients who paid you as a contractor must send Form 1099-NEC, by February 1, 2027 (January 31 falls on a Sunday). If a form is missing, ask the payer, then call the IRS.

    Our guide · Source

  2. Feb 16Tue

    Brokerage 1099-B forms due to investors

    Brokers must send Form 1099-B (sales of stocks, funds and other securities in 2026) by February 16, 2027, a day late because February 15 is Washington's Birthday. Wait for it, and for any corrected copy, before filing.

    Our guide · Source

April 2027

  1. Apr 1Thu

    First RMD due if you turned 73 in 2026

    If you turned 73 in 2026, take your first required minimum distribution (for 2026) from traditional IRAs by April 1, 2027. Waiting until April means a second RMD (for 2027) is also due by December 31, 2027; a missed RMD can cost a 25% excise tax (10% if corrected in time).

    Our guide · Source

  2. Apr 15Thu

    1st-quarter 2027 estimated tax payment due

    Pay the first 2027 estimated tax installment if withholding will not cover your 2027 tax (self-employment, investment or other income without withholding). Late or short payments add an underpayment penalty.

    Our guide · Source

  3. Apr 15Thu

    Last day for 2026 HSA contributions

    If you had HSA-eligible coverage in 2026, you can contribute for 2026 until April 15, 2027 (designate the deposit as a 2026 contribution). A filing extension does not extend this deadline.

    Our guide · Source

  4. Apr 15Thu

    Last day for 2026 IRA and Roth IRA contributions

    You can still make a 2026 traditional or Roth IRA contribution until the April 15, 2027 filing deadline; tell your IRA provider it is for 2026. A filing extension does not extend this deadline.

    Our guide · Source

  5. Apr 15Thu

    2026 tax returns due (or file for an extension)

    File your 2026 Form 1040 and pay any tax owed by April 15, 2027. If you need more time to file, submit Form 4868 by the same day; an extension does not extend the time to pay, so interest and penalties run on unpaid tax.

    Our guide · Source

May 2027

  1. May 1Sat

    New I bond rate for bonds bought from May 1

    Treasury resets the I bond fixed rate and inflation rate every May 1. Compare the announced rate with the current one: buying by the end of April locks in the old fixed rate for the life of the bond.

    Our guide · Source

June 2027

  1. Jun 15Tue

    2nd-quarter 2027 estimated tax payment due

    Pay the second 2027 estimated tax installment. June 15 is also the automatic filing deadline for U.S. citizens and residents living and working abroad.

    Our guide · Source

July 2027

  1. Jul 1Thu

    New federal student loan rates for 2027-28

    Direct Loans first disbursed from July 1, 2027 through June 30, 2028 carry a fixed rate set from the last 10-year Treasury note auction before June 1, 2027. Loans you already have keep their rate.

    Our guide · Source

  2. Jul 1Thu

    Second federal student loan rehabilitation allowed

    From July 1, 2027, a borrower whose federal student loan is in default can rehabilitate it a second time (the limit was once). A second rehabilitation cannot start before this date.

    Our guide · Source

September 2027

  1. Sep 15Wed

    3rd-quarter 2027 estimated tax payment due

    Pay the third 2027 estimated tax installment if withholding does not cover your tax. Late or short payments add an underpayment penalty.

    Our guide · Source

October 2027

  1. Oct 1Fri

    2028-29 FAFSA opens (by law, no later than Oct 1)

    The FAFSA for the 2028-29 school year must be available by October 1, 2027. File early: many state and college aid deadlines are first-come, first-served and fall months before the federal deadline.

    Our guide · Source

  2. Oct 14Thu

    Social Security 2028 COLA announced (expected) expected

    The 2028 cost-of-living raise is set from third-quarter CPI-W, and SSA has announced it on the morning BLS releases September CPI; BLS has scheduled that release for October 14, 2027 at 8:30 a.m. ET. The raise applies to benefits paid from January 2028.

    Our guide · Source · basis: BLS CPI release schedule (September 2027 CPI on Oct 14, 2027) is official; the COLA announcement date is not. Statutory backstop: 42 USC 415(i)(2)(D) requires publication within 45 days after the quarter ends (by Nov 14, 2027).

  3. Oct 15Fri

    Extended 2026 tax returns due

    If you filed Form 4868 by April 15, file your 2026 return by October 15, 2027. There is no further automatic extension, and interest on unpaid tax has run since April 15.

    Our guide · Source

  4. Oct 15–Dec 7

    Medicare Open Enrollment for 2028 plans

    Compare and switch Medicare Advantage and Part D drug plans for 2028; changes take effect January 1, 2028. If you do nothing, your current plan usually renews with its new 2028 costs.

    Our guide · Source

November 2027

  1. Nov 1–Jan 15, 2028

    ACA Marketplace Open Enrollment for 2028 (expected) expected

    Shop, renew or change a HealthCare.gov plan for 2028. The 2028 dates are not announced yet: the 2025 rule that would end Open Enrollment by December 31 was struck in court in June 2026, and CMS kept the November 1 to January 15 window for 2027; state exchanges set their own dates.

    Our guide · Source · basis: 45 CFR 155.410(e)(4) (Nov 1 - Jan 15) as applied by CMS after City of Columbus v. Kennedy, No. 1:25-cv-2114 (D. Md. June 12, 2026). eCFR still prints 155.410(e)(5) (end by Dec 31, max 9 weeks, for 2027+). CMS has not published PY2028 dates.

  2. Nov 1Mon

    New I bond rate for bonds bought from Nov 1

    Treasury resets the I bond fixed rate and inflation rate every November 1. Buying by the end of October locks in the old fixed rate for the life of the bond.

    Our guide · Source

  3. Nov 8–Dec 13

    FEHB and PSHB Open Season for 2028 (expected) expected

    Federal employees, annuitants and postal workers can change FEHB or PSHB plans and enrollment type for 2028. OPM confirms the dates each year; changes take effect the first pay period of January 2028.

    Our guide · Source · basis: 5 CFR 890.301(f)(1): Monday of the second full workweek in November (Nov 8, 2027) through Monday of the second full workweek in December (Dec 13, 2027); OPM may modify (890.301(f)(2)). 2026 Open Season Nov 9 - Dec 14 follows the same rule.

December 2027

  1. Dec 15Wed

    Pick an ACA plan by Dec 15 for Jan 1 coverage (expected) expected

    On HealthCare.gov, plans picked by December 15 have started January 1; later picks start February 1. Confirm on HealthCare.gov once CMS posts the 2028 dates; state exchanges differ.

    Our guide · Source · basis: 45 CFR 155.410(f)(3) (pre-2025 text applied by CMS for PY2027); HealthCare.gov dates page (current cycle). Not yet published for PY2028.

  2. Dec 31Fri

    Last 2027 paycheck to make 401(k)/TSP deferrals

    Employee 401(k), 403(b) and TSP deferrals count toward the year they come out of your pay, so only paychecks dated in 2027 can fill the 2027 limit. Change your percentage early enough for your final payroll runs.

    Our guide · Source

  3. Dec 31Fri

    2027 required minimum distributions due

    Take your 2027 RMD from IRAs and old 401(k)s (and your second RMD if you delayed your first to April 1, 2027). December 31, 2027 is a federal holiday (New Year's Day observed), so ask your custodian for its earlier cutoff; a missed RMD can cost a 25% excise tax (10% if corrected in time).

    Our guide · Source

  4. Dec 31Fri

    Last day for a 2027 Roth conversion

    A Roth conversion is taxed in the year the money leaves the traditional IRA, so it must be completed by December 31 to count for 2027 (there is no April grace period). Banks are closed that day, so start well before.

    Our guide · Source

  5. Dec 31Fri

    Last trading day to book 2027 capital losses

    Sales count in the year of the trade date, not the settlement date. NYSE is open on December 31, 2027 (it is not on its 2027 holiday list) even though it is a federal holiday; watch the 30-day wash-sale rule.

    Our guide · Source

January 2028

  1. Jan 18Tue

    4th-quarter 2027 estimated tax payment due (expected) expected

    Pay the last 2027 estimated tax installment. The statutory January 15, 2028 falls on a Saturday and Monday, January 17 is Martin Luther King Jr. Day, so the due date should move to Tuesday, January 18, 2028; confirm on the 2027 Form 1040-ES.

    Our guide · Source · basis: IRC 6654(c)(2) (January 15 of the following year) + IRC 7503 + 5 USC 6103(a) (MLK Day = third Monday in January = Jan 17, 2028). 2027 Form 1040-ES and Pub 509 (2028) not yet published.

FAQ

When is Tax Day 2027?
Thursday, April 15, 2027, for 2026 tax returns. File your 2026 Form 1040 and pay any tax owed by April 15, 2027. If you need more time to file, submit Form 4868 by the same day; an extension does not extend the time to pay, so interest and penalties run on unpaid tax.

How do I add these dates to my calendar?
Download the .ics file and open it, or subscribe to its web address in Google Calendar (Other calendars > From URL), Apple Calendar (File > New Calendar Subscription) or Outlook (Add calendar > Subscribe from web). A subscription updates itself when we correct or add a date.

What does "expected" mean on a date?
The agency has not published the 2027 date yet. We show the date its usual rule gives and the basis for it, and we update the list and the calendar feed when the official date is out.

Do these deadlines apply to every state?
No. These are federal dates. State tax deadlines, state student aid deadlines and local property tax dates differ; check your state.

General information, not tax, legal or financial advice. Federal dates only, read from IRS, SSA, CMS, OPM, Department of Education, TreasuryDirect, BLS and federal statutes and regulations on October 29, 2026; each item links its source. Disaster relief can postpone IRS deadlines for some areas. "Expected" dates follow the agency's usual rule and can change when it publishes the 2027 date.