Vol. I  ·  No. 2
Friday, October 16, 2026
13 stories in the archive

Front page › Taxes › Every Money Deadline This Season

Every Money Deadline This Season

Updated October 16, 2026 · maintained, not published once

Dates come from the agency that sets them. A deadline drops off once it passes.

In date order. Past dates are removed as they pass.

DateWhatWho it affectsSource
Oct 15 – Dec 7, 2026Medicare Open Enrollment for 2027 coveragePeople with MedicareMedicare.gov
Oct 27–28, 2026Federal Reserve meeting; decision Oct 28Borrowers and saversFederal Reserve
Nov 18, 2026Opt into digital notices to see your 2027 COLA earlySocial Security and SSI recipientsSSA
Oct 22, 2026Payroll and excise deposits due Oct 7–21 without penalty, Isaias countiesAlabama businesses in covered countiesIRS
Dec 8–9, 2026Federal Reserve meeting with projectionsBorrowers and saversFederal Reserve
Jan 20273.6% COLA in benefits for JanuarySocial Security and SSI recipientsSSA
Feb 4, 2027Postponed federal deadlines for Hurricane Isaias, including 2025 extension returns40 Alabama countiesIRS
Feb 8, 2027Postponed federal deadlines for Hurricane Isaias, including 2025 extension returns27 Florida countiesIRS

Taxes

Isaias Victims in Alabama and Florida Get Until February to File

The IRS pushed deadlines to February 4 in 40 Alabama counties and February 8 in 27 Florida counties, including October's extension deadline. Balances due in April did not move.

Individuals and businesses in the parts of Alabama and Florida hit by Hurricane Isaias have more time for many federal tax deadlines, the IRS announced October 14. In Alabama, deadlines falling on or after October 7, 2026, are postponed to February 4, 2027, in 40 counties. In Florida, deadlines falling on or after October 9 are postponed to February 8, 2027, in 27 counties.

Read the full report →

Retirement

Social Security Benefits Rise 3.6 Percent in 2027

The largest cost-of-living adjustment since 2023 reaches checks in January. Medicare's 2027 Part B premium, which comes out of many of those checks, has not been announced yet.

Monthly Social Security benefits and Supplemental Security Income payments will rise 3.6 percent in 2027, the Social Security Administration announced October 14. The increase reaches nearly 72 million Social Security beneficiaries starting with January 2027 benefits, and about 7.3 million SSI recipients starting with payments on December 31, 2026.

Read the full report →

Retirement

Medicare Open Enrollment for 2027 Runs Through December 7

The window to switch drug plans or move between Original Medicare and Medicare Advantage opens today.

Medicare's Open Enrollment period for 2027 coverage runs from October 15 through December 7. During it, people with Medicare can switch from Original Medicare to a Medicare Advantage plan or back, change Medicare Advantage plans, and join, switch or drop a Part D drug plan. Changes take effect January 1.

Read the full report →

IRS, Medicare, HealthCare.gov, Federal Student Aid and the Federal Register.

Around the table

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