The Annual Money Calendar (2026–2027): Every Deadline, Enrollment Window and Rate Reset
Most money mistakes are timing mistakes: a missed enrollment window, a late estimated payment, a rate change nobody saw coming. Here is every date that matters from October 2026 through the end of 2027, with what to do before each one.
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📐 Figures verified Sep 28, 2026 against HealthCare.gov, Medicare.gov, IRS Form 1040-ES, IRS Rev. Procs. 2025-32 and 2026-24, IRS release IR-2025-111, the Federal Reserve's FOMC calendar, TreasuryDirect, StudentAid.gov, the Social Security Administration and CMS. A deadline that lands on a weekend or federal holiday moves to the next business day, and the dates below already reflect that. How we check numbers →
Five dates carry most of the money: Medicare open enrollment ends December 7, 2026; December 15 is the HealthCare.gov deadline for January 1 coverage; December 31 closes the 2026 tax year; the last 2026 estimated tax payment is due January 15, 2027; and April 15, 2027 brings 2026 returns plus the last day for 2026 IRA and HSA contributions.
Numbers That Matter
| Figure | Amount | Source | Verified |
|---|---|---|---|
| HealthCare.gov open enrollment, 2027 coverage | Nov 1, 2026 to Jan 15, 2027; choose by Dec 15 for a Jan 1 start | HealthCare.gov | Sep 28, 2026 |
| Medicare open enrollment, 2027 plans | Oct 15 to Dec 7, 2026 | Medicare.gov | Sep 28, 2026 |
| Last estimated tax payment for 2026 | Jan 15, 2027 | IRS Form 1040-ES | Sep 25, 2026 |
| 2026 returns; last day for 2026 IRA and HSA contributions | Apr 15, 2027 (extended returns: Oct 15, 2027) | IRS | Sep 28, 2026 |
| HSA limit for 2027, self-only / family | $4,500 / $9,000 | IRS Rev. Proc. 2026-24 | Sep 25, 2026 |
| Health FSA limit, 2026 | $3,400; up to $680 can carry into 2027 if the plan allows | IRS Rev. Proc. 2025-32 | Sep 28, 2026 |
| Dependent care FSA limit, from 2026 | $7,500 ($3,750 married filing separately) | P.L. 119-21 §70404 | Sep 28, 2026 |
| 401(k) and IRA limits, 2026 | $24,500 and $7,500 | IRS IR-2025-111 | Sep 25, 2026 |
| Fed rate decisions left in 2026 | Oct 28 and Dec 9 | Federal Reserve | Sep 28, 2026 |
| Federal funds target range | 3.75%–4.00%, in effect since Sep 17, 2026 | FOMC statement, Sep 16, 2026 | Sep 26, 2026 |
| I bond rate resets | May 1 and Nov 1; 4.26% composite for bonds bought May 1 to Oct 31, 2026 | TreasuryDirect | Sep 27, 2026 |
| 2027–28 FAFSA | Open since Sep 23, 2026; federal deadline Jun 30, 2028 | StudentAid.gov | Sep 28, 2026 |
| Social Security COLA | 2.8% for 2026; the 2027 COLA comes with September CPI on Oct 14, 2026 | SSA | Sep 25, 2026 |
| Medicare Part B, 2026 | $202.90 a month; $283 deductible | CMS | Sep 25, 2026 |
| Required minimum distributions | First one by April 1 of the year after you turn 73; later ones by Dec 31 | IRS | Sep 28, 2026 |
October to December 2026: The Busiest Stretch
The last quarter of the year stacks three enrollment windows, two Fed meetings and every deadline that belongs to the 2026 tax year. In order:
- October 14 (Wednesday): The September CPI report, which sets the 2027 Social Security cost-of-living adjustment. SSA announces the COLA the same day.
- October 15 (Thursday): Extended 2025 federal returns are due, and Medicare open enrollment starts.
- October 28 (Wednesday): Fed rate decision. The target range is 3.75%–4.00% after a quarter-point increase on September 16, and the prime rate is 7.00%.
- October and November: Most employers hold benefits open enrollment in this stretch. It is usually your only chance until next fall to change health plans, set FSA elections or switch into an HSA-eligible plan.
- November 1 (Sunday): HealthCare.gov open enrollment opens, and new I bond rates take effect for bonds bought from November 1 through April 30.
- November, usually: The IRS publishes 2027 tax brackets and retirement plan limits, and CMS announces the 2027 Medicare Part B premium.
- December 7 (Monday): Medicare open enrollment ends.
- December 9 (Wednesday): The last Fed decision of 2026.
- December 15 (Tuesday): Last day to choose a HealthCare.gov plan for coverage that starts January 1.
- December 31 (Thursday): The tax-year cutoff; see the December 31 list below.
2027 Month by Month
| Month | Date | What happens | Who it's for |
|---|---|---|---|
| January | Jan 1 | New limits take effect, including the $4,500 / $9,000 HSA limits and 2027 tax brackets; the COLA appears in January benefits | Everyone |
| January | Jan 1 to Mar 31 | Medicare Advantage open enrollment and the Medicare General Enrollment Period | Medicare enrollees and late signups |
| January | Jan 15 (Fri) | Last 2026 estimated tax payment; HealthCare.gov open enrollment ends (plans chosen Dec 16 to Jan 15 start Feb 1) | Self-employed, investors, Marketplace shoppers |
| January | Jan 27 | Fed rate decision | Borrowers and savers |
| January | Late January | The IRS starts accepting 2026 returns on a date it announces | Filers |
| February | Feb 1 (Mon) | W-2s and 1099-NECs are due to workers (January 31 falls on a Sunday); brokerage 1099s follow in mid-February | Employees, contractors, investors |
| March | Mar 17 | Fed rate decision | Borrowers and savers |
| March | Mar 31 (Wed) | Medicare Advantage open enrollment and the General Enrollment Period close | Medicare enrollees |
| April | Apr 1 (Thu) | First required minimum distribution for people who turned 73 in 2026 | Retirees |
| April | Apr 15 (Thu) | 2026 returns and payments due; last day for 2026 IRA and HSA contributions; first 2027 estimated payment; Form 4868 extends the time to file, not to pay | Everyone with income |
| April | Apr 28 | Fed rate decision | Borrowers and savers |
| May | May 1 | New I bond rates for bonds bought May through October | Savers |
| May | Mid-May | The 10-year Treasury auction that sets federal student loan rates for the next school year; the IRS usually publishes 2028 HSA limits this month | Students, HSA owners |
| June | Jun 9 | Fed rate decision | Borrowers and savers |
| June | Jun 15 (Tue) | Second 2027 estimated tax payment | Self-employed, investors |
| June | Jun 30 (Wed) | Federal deadline for the 2026–27 FAFSA | Current students |
| July | Jul 1 (Thu) | New interest rates for federal student loans first disbursed from July 1 | Students and parents |
| July | Jul 28 | Fed rate decision | Borrowers and savers |
| August | Any day | No federal deadlines. A quiet month to check your withholding against what you owed in April | Employees |
| September | Sep 15 (Wed) | Third 2027 estimated tax payment; Fed rate decision the same day | Self-employed, borrowers |
| September | By Oct 1 | The 2028–29 FAFSA opens (the law requires an October 1 launch) | Families with students |
| October | Mid-October | September CPI and the 2028 Social Security COLA | Beneficiaries |
| October | Oct 15 (Fri) | Extended 2026 returns due; Medicare open enrollment for 2028 starts | Extension filers, Medicare enrollees |
| October | Oct 27 | Fed rate decision | Borrowers and savers |
| November | Nov 1 (Mon) | New I bond rates; HealthCare.gov open enrollment for 2028 is expected to open | Savers, Marketplace shoppers |
| December | Dec 7 (Tue) | Medicare open enrollment ends | Medicare enrollees |
| December | Dec 8 | Fed rate decision | Borrowers and savers |
| December | Dec 15 (Wed) | HealthCare.gov deadline for coverage that starts January 1, 2028 | Marketplace shoppers |
| December | Dec 31 (Fri) | The 2027 tax-year cutoff | Everyone |
| January 2028 | Jan 18 (Tue) | Last 2027 estimated tax payment (January 15 is a Saturday and January 17 is Martin Luther King Jr. Day) | Self-employed, investors |
Enrollment Windows
Medicare open enrollment, October 15 to December 7. Anyone on Medicare can switch between Original Medicare and Medicare Advantage, change Advantage plans or change drug plans, and the change takes effect January 1. Plans rewrite premiums, drug lists and pharmacy networks every year, so a plan that fit in 2026 can cost more in 2027. Then, from January 1 to March 31, anyone already in a Medicare Advantage plan gets one more switch: to another Advantage plan, or back to Original Medicare with a drug plan. If you missed your initial window, the General Enrollment Period runs on the same dates and coverage starts the month after you sign up. The Medicare open enrollment checklist walks through the comparison.
HealthCare.gov, November 1 to January 15. For 2027 coverage, the federal marketplace keeps its January 15 closing date: a federal court struck the rule that would have ended open enrollment in December, and CMS has confirmed the longer window for this season, though the government has appealed. December 15 is still the date that matters most, because it is the last day to get coverage that starts January 1. State-run marketplaces set their own closing dates. Update your 2027 income estimate before you choose, since it sets your premium tax credit. The ACA open enrollment checklist and the subsidy cliff guide cover the income side.
Employer open enrollment, usually October or November. This is when you set next year's health FSA election (up to $3,400 in 2026; the 2027 limit arrives with the IRS's fall update), your dependent care FSA, which now goes up to $7,500, and whether you move to an HSA-eligible plan. Most elections are locked for the year unless you have a qualifying life event.
The FAFSA, open now. The 2027–28 form opened September 23, 2026 and uses 2025 tax information. The federal deadline is June 30, 2028, but states and colleges set far earlier deadlines, and some state grants go first come, first served.
Life events open their own windows. Losing job-based coverage, marriage, a birth or a move usually opens a 60-day Special Enrollment Period on HealthCare.gov, and job changes let you revisit workplace elections.
Rate Resets and Announcements
Fed decisions. The remaining 2026 decisions are Oct 28 and Dec 9. The Fed's tentative 2027 calendar puts decisions on Jan 27, Mar 17, Apr 28, Jun 9, Jul 28, Sep 15, Oct 27 and Dec 8. The prime rate moves with the top of the target range (now 4.00% plus 3, or 7.00%), and card and home equity rates tied to prime usually follow within a billing cycle or two. What a Fed hike changes covers which balances move.
I bonds, May 1 and November 1. Treasury sets a new rate twice a year. Bonds bought from May 1 through October 31, 2026 earn a 4.26% composite rate (a 0.90% fixed rate plus inflation) for their first six months, and each bond's rate then resets every six months from its issue month.
Federal student loans, July 1. Rates for new federal loans reset each July 1, set from the May auction of the 10-year Treasury note. Existing federal loans keep their fixed rates.
Social Security and Medicare, January. The 2026 COLA was 2.8%, and the 2027 COLA is set by the September CPI report on October 14. It shows up in January 2027 benefits; SSI recipients get it in the payment dated December 31, 2026, because January 1 is a holiday. The Part B premium is $202.90 a month in 2026, with a $283 deductible, and the 2027 figures usually arrive in November. Income-related surcharges use your tax return from two years earlier, so your 2025 income sets 2027 premiums.
Tax limits, January 1. The 2027 HSA limits are already set at $4,500 self-only and $9,000 family (up from $4,400 and $8,750), plus $1,000 if you're 55 or older. The 2026 limits for 401(k) plans ($24,500) and IRAs ($7,500) will be replaced by 2027 figures the IRS usually announces in the fall, along with 2027 tax brackets and the gift tax annual exclusion ($19,000 per recipient for 2026).
The December 31 List
These have to happen inside the tax year, so the last business day of the year is the real deadline:
- 401(k), 403(b) and 457 contributions must come out of 2026 paychecks. If you want to catch up, change your election before the last payroll runs.
- Required minimum distributions for 2026. The one exception is your first RMD, which can wait until April 1, 2027, at the cost of taking two in 2027.
- Roth conversions count in the year you do them.
- Tax-loss harvesting sales must trade by December 31.
- Charitable gifts, including qualified charitable distributions from an IRA once you're 70½.
- Health FSA money, unless your plan has a grace period (up to two and a half months) or a carryover (up to $680 into 2027).
- 529 contributions for a 2026 state tax deduction in most states; a few allow them until the filing deadline.
- Gifts under the $19,000 annual exclusion.
Not on the list: 2026 IRA and HSA contributions, which stay open until April 15, 2027. RMDs explained covers the distribution rules in detail.
Worked Example: One Household's Year
- December 15: Ana's employer plan is a family HDHP, and she has put $6,000 in her HSA for 2026. The family limit is $8,750, so she has $2,750 of room until April 15, 2027. At a 22% federal bracket, filling it trims about $605 from federal income tax, and more if it goes through payroll. For 2027 she sets $750 a month, which hits the $9,000 family limit exactly.
- December 31: Ana has $500 left in her health FSA. Her plan allows the $680 carryover, so all of it rolls into 2027. Under a grace-period plan she would have until mid-March to spend it instead.
- January 15: Luis, a freelance designer, expects $6,400 of 2026 federal tax that no paycheck withheld. He has paid three $1,600 installments and sends the fourth. For 2027 he marks April 15, June 15, September 15 and January 18, 2028.
- Fed decision days: They carry $20,000 on a home equity line at prime plus 1, or 8.00% today, about $1,600 a year in interest. Each quarter-point move changes that by about $50 a year, and the rate follows the Fed within a billing cycle or two.
- Now: Their daughter Sofia starts college in fall 2027, so they file the 2027–28 FAFSA with their 2025 tax return and aim for their state's deadline, not June 30, 2028.
The Riveras are an illustration. Tax savings assume a 22% federal bracket and ignore state tax; the HELOC rate assumes prime stays at 7.00%.
Decision Rules
If this, then that
- If you're on Medicare → compare plans between October 15 and December 7, even if you're happy with yours.
- If you buy your own coverage → update your 2027 income and choose a plan by December 15.
- If you have income with no withholding → calendar January 15, April 15, June 15 and September 15.
- If you turned 73 in 2026 → taking your first RMD by December 31 avoids stacking two into 2027.
- If you carry a balance tied to prime → note the Fed's decision days and re-check your rate after each one.
- If a student needs aid for 2027–28 → file the FAFSA now; state and school deadlines come long before June 30, 2028.
Mistakes to avoid
- Letting a Medicare or Marketplace plan renew without checking its 2027 costs.
- Treating January 15 as the deadline for January 1 coverage; it's December 15.
- Waiting until April to catch up on 401(k) contributions, which have to come out of 2026 pay.
- Skipping the January 15 estimated payment, the one people forget most.
- Assuming a filing extension also gives you more time to pay.
Related: quarterly estimated taxes explains how much to pay and when; the Medicare open enrollment checklist and the ACA open enrollment checklist cover this fall's two big windows; and the HSA as a retirement account shows why the April 15 HSA deadline matters. More guides are in the Life Guides hub.