Two enrollment seasons are about to run at the same time. Medicare’s annual enrollment period opens October 15 and closes December 7. Most employers open their benefits windows in October and November, and 77% of them do it in that same stretch.
If you’re 65 or older and still working, you’re making both sets of decisions in the same eight-week stretch. And the decisions interact. Choose your workplace plan without looking at Medicare or enroll in Medicare without looking at what your employer covers, and you can create a gap, a penalty, or a tax bill that follows you for years.
The average employee spends 18 minutes on open enrollment. For anyone at this intersection, that number is not close to enough.
What’s Changing in Medicare for 2027
A few things are already confirmed, and they matter for how you compare plans this fall.
The Part D out-of-pocket cap rises to $2,400, up from $2,100 in 2026. Once your prescription spending hits that ceiling, you pay nothing more for covered drugs the rest of the year. The maximum Part D deductible also rises, to $700 from $615.
The temporary Part D premium subsidy ends. A federal stabilization program has been holding down standalone Part D premiums by roughly $16 per month per person. It does not continue into 2027, so premiums on some drug plans may move more than you’re used to seeing. This is the year to actually run the comparison rather than let your plan auto-renew.
Fifteen more negotiated drug prices take effect January 1, 2027. If you take one of them, your plan’s formulary placement may look different than it did last year.
Part B premium and deductible figures for 2027 have not been released yet. They typically come out in the fall, and we’ll flag them when they do.
Three Questions That Decide Your Medicare Timing
If you’re still working, the Medicare decision is not really about which plan looks best. It’s about whether you should be enrolling at all yet. Three things settle it.
How many people does your employer cover? The threshold is 20 employees, and it changes everything. At 20 or more, your group plan pays first and Medicare pays second, which means delaying Part B is often reasonable. Under 20, Medicare generally pays first, and if you haven’t enrolled, your employer plan may pay very little. People find this out at the claim, not at enrollment.
Is your employer’s drug coverage creditable? Your employer is required to tell you each fall whether its prescription coverage is at least as good as Medicare Part D. If it isn’t, and you skip Part D anyway, a late enrollment penalty starts accumulating and stays attached to your premium permanently. That notice arrives bundled with your annual benefits materials, which makes it easy to overlook. If you can’t locate it, ask HR for it directly.
Are you still contributing to an HSA? This is the one that catches the most people. You cannot contribute to a health savings account once you’re enrolled in any part of Medicare. And if you enroll after 65, or claim Social Security after 65, Part A can be applied retroactively up to six months. Contributions made during that retroactive window are subject to an IRS penalty, even when they were made in good faith. The practical rule: stop HSA contributions six months before you plan to enroll or file for Social Security.
None of these are close calls once you have the information. They’re only expensive because nobody asks the question in October.
Your Workplace Benefits Look Different After 65
The voluntary benefits menu deserves a second look at this stage of life, because the value of each line shifts.
Dental and vision get more important, not less. Original Medicare doesn’t cover routine dental or vision care. If your employer offers it, that coverage is doing work Medicare will not do for you.
Disability coverage gets less important. Income replacement protects your working years. The closer you are to the end of them, the less that premium is buying.
Hospital indemnity pairs well with a high-deductible plan. It pays you cash for a hospital stay regardless of your other coverage, which can offset a deductible you’d otherwise pay out of pocket.
Group life is often the cheapest coverage you’ll ever be offered. Group policies typically skip the medical exam, which matters more at 68 than it did at 38.
Legal services, elder care support, and caregiver benefits are also worth reading closely. Many people in this age range are helping an aging parent manage care and housing decisions while sorting out their own coverage in the same fall, and these benefits can help on both fronts.
Where Move Health Comes In
Comparing Medicare plans well is a specialized job. It requires current plan data for your county, your specific prescriptions, and your specific doctors, and it changes every year.
That’s why we work with Move Health, a licensed insurance agency and healthcare planning platform focused on Medicare Advantage, Part D, and Medicare Supplement coverage. Their team runs the plan comparison against your actual medications and providers, and we bring the results back into your financial plan, where the Medicare decision sits alongside your tax picture, your Social Security timing, and your retirement income.
The point of the relationship is that you shouldn’t have to become an expert in something you’ll do once a year. Ask us, and we’ll get you to the right person.
What to Do Before the December 7 Medicare Deadline
We recommend that you pull three documents: your employer’s benefits guide, your employer’s creditable coverage notice, and your current Medicare plan’s Annual Notice of Change, which lists exactly what’s shifting in your coverage for next year.
Then give us a call before you decide anything. If you’re working past 65, this is a conversation, not a form.
We help bring clarity about your options and understanding about what each choice does. That’s what we’re here for, and 18 minutes won’t get you there.
