On extension? Your 2025 return is due October 15
In This Issue
What changed: An extended 2025 return filed after October 15, 2026 draws a 5% monthly penalty.
Today's habit: Match your 2026 tax payments.
Scam Alert: Fake Medicare.gov ads in search results, flagged by the FTC on September 28, 2026.
On the calendar: 2027 plan star ratings post around October 8, 2026.
What Changed
If you took an extension on your 2025 return, you have 14 days left. The IRS confirmed the October 15, 2026 deadline and repeated that an extension buys time to file, not to pay. Miss it and the failure-to-file penalty takes 5% of the unpaid tax for each month, up to 25%. Past 60 days late, the floor is $525 or the full tax owed, whichever is less. A return that shows a refund owes none.
The point: File by October 15, 2026 even if you can't pay in full. On $8,000 of unpaid 2025 tax, each late month adds $400, up to $2,000.
From today, Medicare's Plan Finder prices your own prescriptions under 2027 plans, two weeks before you can switch. The CMS 2027 state fact sheets show how many stand-alone drug-plan members can find a lower premium than they paid in 2026: 100% in California and Maryland, 38.67% in Arizona.
The point: If you hold a stand-alone drug plan, run your list through Plan Finder before December 7, 2026. A $20 monthly gap costs you $240 in 2027.
Today's Habit
Check that the IRS holds every 2026 estimated tax payment you've sent.
The IRS posts each payment by Social Security number, tax year and form. A payment keyed to 2025 instead of 2026, or to your spouse's number, sits in the wrong place while your 2026 account shows a shortfall. You won't hear about it until a notice arrives next year.
Skipping the check costs interest. The IRS underpayment rate is 7% a year, compounded daily, for the quarter that starts October 1, 2026. A $10,000 payment the IRS can't match costs you at least $700 a year until someone fixes it.
For extension filers the stakes run higher. The failure-to-file penalty falls on tax due minus tax paid on time, so a payment the IRS can't see turns into penalty base after October 15, 2026.
- Open your IRS online account and sign in. If you set up an IP PIN, it's the same login.
- Go to Payments and select tax year 2026.
- Put your bank statements or check register next to the screen, and list every 2026 payment you've made so far.
- Match each 2026 payment on date and amount. On extension? Find your 2025 extension payment under tax year 2025 too.
- Missing one? Write down its date, amount and confirmation number, and call the IRS before you pay a second time.
When it's done, every 2026 payment in your records appears on the IRS screen, under 2026, for the right amount, and the bank records sit in a folder you'll find next spring.
Scam Alert
Plan Finder opened for 2027 today, and the fakes sit above it in your search results. The FTC warned on September 28, 2026 that scammers and dishonest businesses pay to appear at the top when you search for Medicare help.
How it arrives: you search for Medicare enrollment and the first results are ads. Some lead to addresses built to look like a government site, logos included.
What it asks for: your Medicare number, a phone call, or payment for a plan. The FTC says you can end up paying for a plan that isn't health insurance, or hand over enough for medical identity theft.
The one tell: a small "Ad" or "Sponsored" label, or an address that doesn't end in .gov.
What to do: type Medicare.gov into the address bar yourself, or call 800-633-4227. Report a fake site at ReportFraud.ftc.gov. For help comparing plans, the FTC points you to your State Health Insurance Assistance Program.
On the Calendar
October 8, 2026: 2027 star ratings for Medicare health and drug plans post on Medicare.gov, on or around this date.
October 14, 2026: The BLS releases September's Consumer Price Index, the last inflation reading before the 2027 COLA is set.
General information, not personalised advice. Every figure here comes from the SSA, the IRS, the CMS or the plan document, and carries the year it applies to. Corrections run at the top of the next issue.
— Robert Kessler