I understand why. It looks like every other piece of insurance mail, which is to say it looks like a chore. But that envelope is your plan telling you, in writing and in advance, exactly how it intends to treat you differently next year. Ignoring it is how a $40 prescription becomes a $240 prescription in January, and nobody broke a single rule.

Seven weeks, one decision

Medicare’s Annual Enrollment Period runs Oct. 15 through Dec. 7. Those seven weeks are the one stretch of the year when almost anyone on Medicare can switch plans, change drug coverage or move between Original Medicare and Medicare Advantage, with the new coverage starting Jan. 1.

Miss it, and with limited exceptions you’re married to your current plan for another year, including whatever that September envelope said it was about to become.

Plans change more than people assume. Premiums move. Drug formularies get reshuffled, and a medication that was Tier 2 this year can be Tier 4 next year. Doctor networks shift, and in a state like ours, where one hospital system can dominate an entire valley, a network change isn’t an inconvenience. It can mean driving from Brigham City to Salt Lake for a specialist you used to see down the street.

The number that isn’t final yet

Here’s the wrinkle this particular fall: You’ll be shopping before all the prices are posted.

The standard Part B premium is $202.90 a month in 2026, after last year’s jump of nearly 10%. The Medicare trustees project roughly $209.50 for 2027, which would be a mercifully small increase, though some private forecasters think the final number lands closer to $215, and the government won’t confirm it until November, right in the middle of enrollment season.

So build your comparison on the plan details you can verify, and leave a little cushion in the budget for the premium announcement. A plan that only works if every projection comes in on the low side isn’t a plan. It’s a wish.

The surcharge that reads your old mail

While we’re on premiums, remember that what you pay for Medicare is tied to what you told the IRS two years ago. The IRMAA surcharge starts at $109,000 of income for a single filer and $218,000 for a couple, and it’s a cliff, not a slope.

The two-year lookback is what trips people. Your 2027 premium keys off your 2025 return, which is already filed and finished. But the return you’ll file for 2026 is still very much in play, and it sets your 2028 premium. The IRA withdrawal you take this December, the property you sell, the conversion you size carelessly – all of it lands on a Medicare bill two years down the road.

This is why I keep saying income planning and Medicare planning are the same conversation wearing different name tags.

Predictable income makes this whole season easier

One quiet advantage of guaranteed income is that it’s boring on purpose. A Fixed Index Annuity with a lifetime income rider pays a number you know in advance, every month, regardless of what the market did. When you know your income to the dollar, you can see an IRMAA cliff coming years out and steer around it, and you can judge a Medicare plan’s out-of-pocket maximum against a budget that actually holds still.

I’ll be straight about the fine print, as always: Income from an annuity funded with IRA money is still ordinary income when it arrives. The advantage isn’t that the tax disappears. The advantage is that the income stops surprising you, and people who aren’t surprised make better enrollment decisions.

Do the homework once a year

So here’s the October assignment, and it takes one evening, not a weekend. Open the envelope. Read what your premium, your deductible and your drug tiers become in January. Make a list of your medications and your doctors, and check both against any plan you’re considering, because the plan with the lowest premium and the plan with the lowest total cost are frequently not the same plan.

Utahns will spend three weekends this fall getting the snowblower running and the food storage rotated. Your Medicare coverage deserves one evening of the same discipline.

The envelope isn’t junk mail. It’s the bill for next year, mailed early enough that you can still do something about it.

Lyle Boss, The REAL BOSS Financial, a native Utahn and retirement specialist who has spent decades helping families across Utah and the Mountain West build secure, income-focused retirement plans. Boss Financial, 955 Chambers St. Suite 250, Ogden, UT 84403. Telephone: 801-475-9400. https://www.safemoneylyleboss.com.