Every Retirement Deadline That Matters
The dates the IRS enforces, the windows that close without warning, and the deadlines that cost people real money when they miss them.
The retirement system runs on deadlines. Some are tied to the calendar year. Some are tied to your tax filing date. Some are rolling windows that start the day you receive a check or make a contribution. Missing any of them triggers consequences that range from a 6% annual penalty to a full reclassification of a tax-free transaction into taxable income. The IRS does not send reminders for most of these. Your custodian may or may not flag them. The responsibility is on you to know when each window opens, when it closes, and what happens if you are one day late.
January 1: New Contribution Year Opens
The new tax year opens a fresh contribution window for every retirement account. IRA contributions (traditional and Roth) can be made for the new tax year starting January 1. Employer plan deferrals reset to the new annual limit. Catch-up contributions reset.
If you are turning 50 during the year, your catch-up eligibility starts January 1, not your birthday.
January 1 is also the date the 5-year clock starts for Roth conversions. A conversion made in December and a conversion made in January of the same year share the same 5-year start date of January 1 of that year. If you are planning conversions, converting in January gives you the longest runway within a given 5-year clock.
January 1 is also the date your prior-year December 31 IRA balance gets locked in for the current year's RMD calculation and pro-rata formula denominator.
January 31: 1099-R Due
Your custodian must send you Form 1099-R by January 31 of the year following any distribution. The IRS receives a copy on the same timeline. This form reports every dollar that left your retirement account during the prior year, including distributions, rollovers, Roth conversions, and returned excess contributions.
If you had distributions from multiple custodians, you will receive a separate 1099-R from each one. Do not file your tax return until you have every 1099-R. The IRS will have them all and will compare them against your return.
If a 1099-R does not arrive by mid-February, contact the custodian. A missing form does not extend your filing deadline, and filing without it almost guarantees a mismatch.
Related: Understanding Your Form 1099-R
April 1: First-Year RMD Grace Period
If you turn 73 during the prior year, your first RMD can be delayed until April 1 of the following year. This is the only RMD that gets a grace period. Every subsequent RMD is due December 31.
The April 1 delay is a penalty-avoidance mechanism, not a planning strategy. If you delay your first RMD to April 1, your second RMD is still due December 31 of that same year. Two taxable distributions in one calendar year. The combined income can push you into a higher bracket and trigger IRMAA surcharges two years later.
Taking your first RMD in the year you turn 73 (by December 31) avoids the double-distribution problem entirely.
April 15: Contribution Deadline and Tax Filing
April 15 is the deadline for IRA contributions for the prior tax year. You can make a traditional or Roth IRA contribution anytime between January 1 and April 15 and designate it for the prior year.
After April 15, the contribution window for the prior year closes permanently (unless you filed a tax extension, which extends the filing deadline but does not extend the IRA contribution deadline).
April 15 is also the tax filing deadline, which matters for excess contribution corrections. If you made an excess contribution to a Roth IRA and want to withdraw it penalty-free, the excess plus the Net Income Attributable must be removed by your tax filing deadline, including extensions. April 15 is the default. If you file an extension, the correction deadline moves to October 15. Missing both deadlines means the 6% annual penalty applies for every year the excess remains.
Related: Excess Contribution Correction Tool
May 31: Form 5498 Due
Your IRA custodian must file Form 5498 with the IRS and send you a copy by May 31. This form reports contributions, rollover deposits, fair market value, and RMD status for the prior tax year.
It arrives after most people have already filed their return, which is by design. The IRS collects distribution data first (1099-R in January), your return second (January through April), and contribution data last (5498 in May). The matching process runs after all three are in the system.
When the 5498 arrives, compare it against what you reported on your return. If the rollover amount in Box 2 does not match what you reported, contact your custodian immediately. The IRS will find the discrepancy on their own timeline. You want to fix it on yours.
Related: Understanding Your Form 5498
June 15: Estimated Tax Payments
If you did a Roth conversion or took a large distribution earlier in the year and did not have enough tax withheld, June 15 is the second quarterly estimated tax payment deadline.
Underpaying estimated taxes can trigger an underpayment penalty when you file your return. The IRS expects you to pay tax throughout the year as income is earned or received. A $100,000 Roth conversion in January with no withholding and no estimated payments until April of the following year will almost certainly trigger the penalty.
The safe harbor to avoid the underpayment penalty is to pay at least 100% of your prior-year tax liability (110% if your AGI exceeded $150,000) through a combination of withholding and estimated payments.
October 1: SIMPLE IRA Establishment
A SIMPLE IRA must be established by October 1 of the year it will take effect. You cannot set up a SIMPLE IRA in December and backdate it. Employee notification requirements apply before the plan takes effect.
This is the most restrictive establishment deadline of any small-business retirement plan. If you miss October 1, you cannot have a SIMPLE IRA for the current year.
A SEP IRA can still be established later (by the tax filing deadline), and a Solo 401(k) must be established by December 31.
Related: SIMPLE IRA Guide
Compare options: Small-Business Retirement Plans Guide
October 15: Extended Filing and Recharacterization
If you filed a tax extension, October 15 is the extended filing deadline. It is also the extended deadline for several retirement account corrections.
An excess IRA contribution can be withdrawn penalty-free (with NIA) by October 15 if you filed an extension. A recharacterization of an IRA contribution (moving a Roth contribution to traditional or vice versa) must be completed by the tax filing deadline including extensions, which is October 15 for people who filed an extension.
After October 15, the recharacterization option for the prior year closes. The excess contribution correction window also closes. Any excess remaining after this date triggers the 6% annual penalty until it is removed or absorbed in a future year.
Related: Recharacterization Calculator
December 31: RMDs, Roth Conversions, and Plan Establishment
December 31 is the busiest deadline in the retirement calendar.
Required Minimum Distributions for the current year must be taken by December 31 (except for the first-year grace period discussed above).
Roth conversions must be completed by December 31 to count for the current tax year. There is no extension. A conversion initiated on December 30 that does not settle until January 2 is a next-year conversion.
The December 31 fair market value of all your traditional, SEP, and SIMPLE IRAs is the number used for next year's RMD calculation and the pro-rata formula denominator.
A Solo 401(k) must be established by December 31 to accept contributions for the current year (though contributions themselves can be made until the tax filing deadline).
Missing December 31 for any of these means waiting an entire year for the next opportunity, except for the RMD, where missing it means a 25% penalty.
Related: Roth Conversion Rundown
Related: RMD Mistakes & Fixes
Related: Solo 401(k) Guide
Printable version: Retirement Deadline Calendar (PDF download)
Rolling Deadlines: 60 Days, 12 Months, Two Years, Five Years
Some retirement deadlines are not tied to a calendar date. They start running when a specific event occurs.
The 60-Day Rollover Window
The 60-day rollover window starts the day you receive a distribution. Not the day you requested it. Not the day the check was dated. The day the money landed in your hands. Sixty calendar days. No extensions unless you qualify for self-certification under Revenue Procedure 2020-46.
The 12-Month Once-Per-Year Rule
The 12-month once-per-year rule for indirect IRA-to-IRA rollovers starts on the date you receive the distribution. If you received a distribution on March 10, you cannot do another indirect IRA-to-IRA rollover until March 11 of the following year. This is a rolling 12-month window, not a calendar year.
The SIMPLE IRA Two-Year Rule
The SIMPLE IRA two-year rule starts on the date of your first contribution to the SIMPLE, not the date the account was opened. Any rollover out of the SIMPLE to a non-SIMPLE account before two years triggers a 25% penalty.
The Roth Conversion 5-Year Rule
The Roth conversion 5-year rule starts on January 1 of the year of the conversion. Each conversion has its own 5-year clock. If you convert at age 56, the converted amount is subject to the 10% early withdrawal penalty if withdrawn before five years have passed (and before age 59½).
The Roth IRA Earnings 5-Year Rule
The Roth IRA 5-year rule for earnings starts on January 1 of the year you open your first Roth IRA. This is a one-time clock. Once five years have passed and you are over 59½, all Roth earnings are tax-free and penalty-free.
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Frequently Asked Questions
When is the deadline to contribute to an IRA for the prior year?
April 15 of the following year. You can make traditional or Roth IRA contributions for the prior year anytime between January 1 and April 15. Filing a tax extension does not extend the IRA contribution deadline. Only the excess contribution correction deadline moves to October 15 with an extension.
Can I delay my first RMD?
Yes, but only the first RMD. If you turn 73 during the year, you can delay that first RMD until April 1 of the following year. Every subsequent RMD is due December 31. Delaying the first RMD means taking two RMDs in the same calendar year, which can push you into a higher bracket and trigger IRMAA surcharges two years later. See RMD Mistakes & Fixes for the trade-off.
When is the deadline for a Roth conversion?
December 31 of the year you want the conversion to count for. There is no extension. A conversion initiated on December 30 that does not settle until January 2 is treated as a conversion for the following year. Unlike IRA contributions, Roth conversions cannot be backdated to the prior year.
What is the 60-day rollover deadline?
60 calendar days from the date you receive the distribution. The clock starts when the money lands in your hands, not when you requested it or when the check was dated. Day 60 is a rollover; Day 61 is a taxable distribution. Self-certification waivers under Revenue Procedure 2020-46 are possible for 12 specific reasons, but the hardship bar is high. See the Rollover IRA Guide for details.
When must a SIMPLE IRA be established?
October 1 of the year the plan takes effect. Unlike SEP IRAs (which can be established up to the tax filing deadline including extensions), SIMPLE IRAs cannot be backdated. Employee notification requirements also apply before the plan takes effect. Missing October 1 means waiting until next year.
When is Form 5498 due?
May 31 of the year following the tax year. Custodians file it with the IRS and send you a copy on the same timeline. It arrives months after most people have filed their tax return. The late arrival is intentional — it lets the IRS match contribution data against the return during the summer and fall matching process. See the Form 5498 guide for the full breakdown.
What is the deadline to fix an excess contribution?
Your tax filing deadline, including extensions. April 15 is the default; October 15 if you filed an extension. You can withdraw the excess plus the Net Income Attributable without the 6% penalty if removed by that deadline. Missing the deadline means the 6% annual penalty applies for every year the excess remains. The Excess Contribution Correction Tool runs the NIA formula.
When do RMDs have to be taken each year?
December 31 of the year the RMD is required for. The only exception is the first-year grace period, which lets you delay your first RMD until April 1 of the following year. Miss the December 31 deadline and the penalty is 25% of the amount you were supposed to take, reduced to 10% if corrected within two years.
What is the recharacterization deadline?
Your tax filing deadline including extensions. April 15 is the default; October 15 if you filed an extension. Recharacterization only applies to IRA contributions (moving a Roth contribution to traditional or vice versa). Roth conversion recharacterizations were eliminated by the Tax Cuts and Jobs Act and are no longer available.
What is the SIMPLE IRA two-year rule deadline?
Two years from the date of your first contribution to the SIMPLE. Not the date the account was opened and not the date you were hired. Any rollover out of the SIMPLE to a non-SIMPLE account before two years have passed triggers a 25% early distribution penalty instead of the standard 10%.
Education-only disclaimer
This guide is for general education and information only. It does not provide individualized investment, tax, or legal advice, and does not establish a client relationship with any firm or individual. Always consult your own tax professional, financial advisor, or legal counsel before making decisions about your accounts, investments, or retirement strategy.
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