Why deadlines are worth a calendar reminder
Most money penalties come from a date, not from a hard calculation. Miss a health insurance enrollment window and you may wait a year. Skip a required retirement withdrawal and you can owe a penalty tax. This page puts the official dates for the rest of 2026 and the 2027 tax season in one list, with a countdown for each and a link to the agency that sets it.
The key dates, in order
- October 15 to December 7, 2026: Medicare Open Enrollment. If you have Medicare, you can join, switch or drop a Medicare Advantage plan or a Medicare drug plan. Changes you ask for by December 7 start on January 1. Compare costs with the Medicare costs guide.
- November 1, 2026 to January 15, 2027: Health Insurance Marketplace Open Enrollment. On HealthCare.gov, December 15 is the last day to enroll for coverage that starts January 1. Enroll between December 16 and January 15 and coverage starts February 1. States that run their own Marketplace can use different dates. The ACA subsidy calculator estimates your premium help.
- December 31, 2026: required minimum distributions and 401(k) pay deferrals. If you were 73 or older before 2026, take your 2026 required minimum distribution by this date. If you turned 73 in 2026, you may wait until April 1, 2027 (see that item). Some people who are still working can delay distributions from their current employer's plan. Employee 401(k) contributions must come out of pay received in 2026. The limit is $24,500, plus catch-up amounts if you are 50 or older.
- January 15, 2027: fourth-quarter estimated tax. If you are self-employed or have income without withholding, this is the last 2026 installment. See the guide to estimated quarterly taxes.
- February 1, 2027: W-2 and most 1099 forms. The legal date is January 31, a Sunday in 2027, so the next business day applies. Employers send Form W-2 and businesses send Form 1099-NEC (for $2,000 or more paid to a contractor in 2026). Banks and payment apps send Forms 1099-INT, 1099-DIV and 1099-K by the same date.
- February 16, 2027: brokerage forms. Forms 1099-B, 1099-S and 1099-DA are due February 15, which is Washington's Birthday, so the date moves to Tuesday.
- April 1, 2027: delayed first RMD. If you turned 73 in 2026, you may wait until this date for your first distribution, but then you take two in 2027.
- April 15, 2027: Tax Day. Your 2026 federal return and any tax owed are due, and so is the last day for 2026 IRA and HSA contributions. Form 4868 extends the time to file to October 15, 2027, not the time to pay.
What if the date falls on a weekend or holiday?
The IRS moves a due date that lands on a Saturday, a Sunday or a legal holiday to the next business day. That is why the January 31 forms deadline becomes February 1 in 2027, and why mid-February becomes February 16. April 15, 2027 is a Thursday and not a holiday, so Tax Day stays put. Dates marked "Date calculated" on the page come from this rule. The IRS has not yet published its 2027 form instructions, so the page uses the same rule that produced February 2 and February 17 in 2026.
Dates that are not announced yet
The IRS announces the day it starts accepting returns for a new tax year, usually in the winter before the season opens. As of October 16, 2026, it has not announced the opening day for the 2027 season, so the page says so instead of guessing. The tax refund date estimator shows how long refunds take once you file.
How the page works
Every deadline is stored with its date and its official sources. The countdown counts whole days from today's date in New York, the calendar the IRS uses, so it does not change with your time zone. A deadline that has passed moves to the "Past deadlines" list. Choose "Add to calendar (.ics)" on any row, or download the whole list, for a reminder file that works with Apple Calendar, Google Calendar and Outlook. It is created in your browser and nothing is sent anywhere. For release dates of reports such as inflation and jobs numbers, see the economic calendar.
Where the dates come from
The dates come from HealthCare.gov, Medicare.gov and IRS pages and publications, including IRS Publication 1099, Publication 590-A, Publication 969 and the IRS pages on estimated taxes and when to file. The list was last checked on October 16, 2026. Agencies can change dates, and some states, plans and employers use different ones, so open the official page before you act. This page is general information, not tax, legal, insurance or financial advice.
Frequently asked questions
When is the tax filing deadline in 2027?
For 2026 federal income tax returns, the deadline is Thursday, April 15, 2027. Form 4868 gives an automatic six-month extension to file, until October 15, 2027, but it does not extend the time to pay. If you owe tax, estimate it and pay by April 15 to limit penalties and interest.
When does Marketplace Open Enrollment start and end for 2027 coverage?
On HealthCare.gov, Open Enrollment runs from November 1, 2026 to January 15, 2027. To have coverage start on January 1, enroll by December 15. After January 15 you generally need a Special Enrollment Period. Some state-run Marketplaces have different dates, so check your state's website.
When will I get my W-2 and 1099 forms?
Employers and payers must send most of them by January 31, 2027. Because that day is a Sunday, the deadline is Monday, February 1, 2027. Forms from brokers, such as Form 1099-B, are due February 16, 2027.