Open Enrollment 2027: Key Dates and What to Change

When is open enrollment for 2027?

Open enrollment for 2027 depends on where your coverage comes from: your employer sets its own window, FEHB and PSHB Open Season runs November 9 through December 14, 2026, and the ACA Marketplace runs November 1, 2026 through January 15, 2027 in most states.

The federal and Marketplace windows overlap but are not the same, and Medicare’s annual window closes first. If you are helping a parent with Medicare while handling your own employer plan, you are working two deadlines at once.

2027 open enrollment windows by coverage type. Sources: OPM Federal Benefits Open Season Highlights, Plan Year 2027 (September 30, 2026); CMS statement on City of Columbus v. Kennedy (August 4, 2026); HealthCare.gov; Medicare.gov. As of October 2026. State-run Marketplaces set their own deadlines (table below).

Why did the Marketplace deadline almost change?

A 2025 federal rule would have ended HealthCare.gov enrollment on December 15 starting this year, but a federal court vacated it in June 2026 and CMS confirmed the January 15, 2027 deadline in August. HHS has appealed, so the schedule could still change for 2028 coverage. Our practical advice is unchanged either way: pick your plan by December 15 so there is no gap on January 1. You can confirm dates on HealthCare.gov.

Which open enrollment decisions matter most for high earners?

Four elections carry nearly all of the financial weight: your health plan design, your HSA and FSA contributions, your disability coverage, and your life coverage. Everything else in the portal (wellness credits, legal plans, pet insurance) is worth a glance, not an evening.

Here is the order we review them in, because each answer feeds the next:

1. Health plan. Run Worst-Year Math (below) on every plan you’re offered, including your spouse’s.
2. Tax-advantaged accounts. Your plan choice decides whether you can use an HSA or a general health FSA. Set the dependent care FSA separately.
3. Disability. Confirm the monthly cap, what earnings count, and whether benefits would be taxable.
4. Life. Size coverage to obligations, then decide whether group supplemental or individual term is the cheaper way to hold it.
5. Cash reserves. Whatever plan you choose, make sure your emergency fund can absorb its out-of-pocket maximum.

Should you choose an HDHP with an HSA or a PPO in 2027?

Choose the high-deductible plan if you can cover its out-of-pocket maximum from cash without strain and you will actually fund the HSA; choose the PPO if a bad medical year would land on a credit card. Comparing premiums alone gets this wrong in both directions, which is why we use a method we call Worst-Year Math.

How does Worst-Year Math work?

Worst-Year Math compares each plan’s full annual cost in two scenarios, a quiet year and a year you hit the out-of-pocket maximum, after subtracting what the employer puts in your HSA and the tax you save on your own contributions.

1. Write down each plan’s annual premium (your share, not the employer’s).
2. Quiet year: add a modest amount of routine spending.
3. Worst year: add the plan’s out-of-pocket maximum instead.
4. For the HDHP, subtract any employer HSA contribution.
5. For the HDHP, subtract the tax savings on what you contribute (your contribution times your marginal rate). Remember the employer’s deposit counts toward the annual HSA limit.

A hypothetical example shows why the answer is rarely obvious. Below, the HDHP is cheaper in a quiet year and more expensive in the worst year:

Hypothetical and illustrative only; not a projection and not any actual client. Plan figures are invented for the example. Assumes the 2027 family HSA limit of $9,000 (IRS Rev. Proc. 2026-24) and the 24% federal bracket (2026 brackets, IRS Rev. Proc. 2025-32). Excludes state tax and any payroll-tax savings from contributing through a cafeteria plan. The $8,000 contributed stays in the family’s HSA; only the tax saved is counted as a cost reduction.

The HDHP saves about $4,100 in the quiet year and costs about $3,900 more in the worst year. That is a genuine bet, and the right side of it depends on two things: how likely a big medical year is for your household, and whether you have the cash to fund both the HSA and the deductible. In our experience, the people who get the most out of an HDHP are the ones who can cash-flow the worst year without touching a credit card. If that’s not you yet, the PPO is not a mistake.

What limits the HSA route?

You can only contribute to an HSA while you are covered by an HSA-qualified plan and have no disqualifying coverage. Three common snags: a spouse’s general-purpose health FSA disqualifies you, enrolling in Medicare ends contributions, and the family limit is shared between spouses. Our HSA vs. FSA guide covers the eligibility rules in depth.

Two rule changes widen access. Starting in 2026, bronze and catastrophic plans are treated as HSA-compatible even if they don’t meet the usual HDHP definition, and certain direct primary care arrangements no longer disqualify you (IRS Notice 2026-05). The law also made permanent the rule letting a plan cover telehealth before the deductible without breaking HSA eligibility.

What are the HSA and FSA limits for 2026 and 2027?

For 2027, the HSA limit is $4,500 for self-only coverage and $9,000 for family coverage, up from $4,400 and $8,750 in 2026 (IRS Rev. Proc. 2026-24). The 2026 health FSA limit is $3,400, the dependent care FSA limit is $7,500 per household, and the IRS has not yet announced the 2027 health FSA limit.

HSA and FSA contribution limits, tax years 2026 and 2027. Sources: IRS Rev. Proc. 2025-32 and One Big Beautiful Bill Act (2026 figures); IRS Rev. Proc. 2026-24 (2027 HSA figures). 2027 health FSA figures are published in the IRS’s annual inflation adjustments, expected late October or November 2026. As of October 2026.

A few rules that trip people up every fall:

• FSAs don’t roll forward on their own. Your health plan usually renews automatically; your FSA election does not. Federal employees must re-enroll in FSAFEDS every year.
• The dependent care FSA got bigger. The household limit rose from $5,000 to $7,500 starting in 2026, but your employer’s plan has to adopt the higher cap, and the benefit is limited to the lower-earning spouse’s earned income. For dual-income families paying for daycare, this is one of the cleaner tax decisions of the year.
• “Use it or lose it” still applies to health FSAs, apart from a carryover or grace period if your employer offers one. Elect what you are confident you’ll spend: orthodontics, recurring prescriptions, therapy copays.

How much disability insurance do you need through work?

You need enough that your household could cover its essential expenses on the disability benefit alone, and for most high earners the group plan’s monthly cap, not its “60% of salary” headline, decides whether that’s true. Disability is the election we find most often under-examined among high earners, and it protects the asset everything else in the plan depends on: your income.

Social Security’s actuaries project that a worker who turns 20 in 2026 has a 24% chance of becoming disabled before full retirement age (SSA Actuarial Note 2026.6). That uses Social Security’s strict definition, an inability to do any substantial work for at least a year, so shorter or partial disabilities that still interrupt a paycheck come on top of it. Open enrollment is usually the one time a year you can increase group coverage without answering health questions.

Four things to check in your plan documents:

1. The monthly maximum. Group long-term disability commonly replaces around 60% of pay up to a fixed monthly cap. Above a certain salary, the cap is the benefit.
2. What counts as pay. Many plans cover base salary only. Bonuses, commissions, and RSU income are often excluded, which matters for the tech professionals and other high earners we serve.
3. Whether benefits would be taxed. If your employer pays the premium with pre-tax dollars, benefits are generally taxable when you receive them. Some employers let you pay the premium with after-tax dollars at enrollment, which generally makes the benefit tax-free.
4. The definition of disability. “Own occupation” coverage pays if you can’t do your job; “any occupation” pays only if you can’t do any reasonable job. Many group plans switch from the first to the second after a set period.

Short-term vs. long-term disability. Short-term disability replaces part of your pay for a few weeks to roughly six months after an illness, injury, or childbirth. Long-term disability starts after that waiting period and can run for years or to retirement age.

Planning a pregnancy? Enroll in short-term disability before you’re pregnant. Most carriers treat an existing pregnancy as a pre-existing condition, so electing coverage after you conceive often means it won’t pay for that birth. We raise this with clients every fall because it is a timing question, not a cost question.

If the group plan falls short, an individual policy can fill the gap; we cover how to think about that in the three types of insurance people forget.

Should you buy supplemental life insurance at open enrollment?

Buy supplemental group life only if you need more coverage than your basic benefit and can’t get comparable individual term coverage for less; group supplemental coverage typically reprices upward as you age and often ends when you leave the employer. Basic employer coverage, commonly one times salary, is rarely enough for a household with young children, a non-working spouse, or a large mortgage.

We generally size life coverage from the obligations, not from a salary multiple: debts that would need paying off, the years of income your family would need replaced, education goals, minus what you’ve already saved. Then we compare two ways to hold it:

• Group supplemental life is easy to buy, sometimes with no medical questions up to a limit, but it is usually priced in age bands that rise every few years and is tied to your job.
• Individual level-term life (a 20- or 30-year policy) locks in a premium for the full term and stays with you between jobs, but you have to qualify medically.

If you have a health condition that makes individual underwriting expensive, the group plan’s no-medical-questions entry can be worth its higher long-run cost. That is a trade-off, not a rule.

For federal employees: FEGLI is not part of Open Season. Outside a rare FEGLI open season, you can add or increase coverage only after a qualifying life event or with proof of insurability. FEGLI Option B premiums also rise with age, so younger, healthy employees often find individual term cheaper over 20 years, while those with health issues may value FEGLI’s easier entry.

What should federal employees review during FEHB Open Season?

Federal employees should compare their current FEHB or PSHB plan against at least two alternatives this Open Season, because OPM reports the average enrollee share of FEHB premiums will rise 10.9% for 2027 after increases of 12.3% in 2026 and 13.5% in 2025. PSHB premiums rise 8.2% on average. Coverage continues automatically if you do nothing, which is exactly why plan drift is so common.

A focused 2026 Open Season review:

1. Check whether your plan is changing or leaving the program. Carriers that exit send notices; if yours is one, you must choose a new plan.
2. Compare total cost, not premium. Use OPM’s plan comparison tool when it goes live in early November and run Worst-Year Math with each plan’s catastrophic limit.
3. Look at FEHB HDHP options. These plans pass part of the premium through to your HSA each pay period; check the pass-through amount in the brochure.
4. Re-elect FSAFEDS. Health and dependent care FSAs do not carry over between years automatically.
5. Review FEDVIP dental and vision. Changes take effect January 1, 2027.
6. Have documents ready if you add a family member. For plan year 2027, OPM requires supporting documentation for anyone added during Open Season.
7. Think about retirement eligibility. To keep FEHB in retirement, you generally need continuous coverage for the five years immediately before you retire. If you’re within that window, avoid any gap. It is one of the inputs we review alongside how your FERS pension is calculated.

Full plan details and dates are on OPM’s Open Season page.

What should self-employed people and early retirees watch on the ACA Marketplace?

Your projected 2027 household income sets your Marketplace subsidy, and since the enhanced premium tax credits expired after 2025, a household above 400% of the federal poverty level receives no premium tax credit at all. One extra dollar of income above that line can cost the entire subsidy. That makes income planning, not plan shopping, the biggest lever for business owners, consultants, and anyone retired before Medicare.

What counts toward the income test (modified adjusted gross income) is broader than salary. Roth conversions, realized capital gains, IRA withdrawals, RSU vesting, and tax-exempt municipal bond interest all count. We sequence conversions around this threshold for clients who buy coverage on the Marketplace, because a conversion that saves tax over a lifetime can cost more in lost subsidy this year. Sometimes paying full premium and converting anyway is still the right call; it depends on the size of the subsidy and the long-term tax math.

Consider a hypothetical solo consultant who expects 2027 income just under the cliff and is weighing a year-end Roth conversion. The question is not “should I convert?” in isolation; it is whether the conversion’s tax value exceeds the subsidy it would forfeit, and whether a smaller conversion keeps both. (Hypothetical and illustrative; no outcome is implied.)

Two more Marketplace points:

• Bronze and catastrophic plans now pair with an HSA starting in 2026 (IRS Notice 2026-05), which gives self-employed buyers a tax-advantaged account that wasn’t available with most of these plans before.
• Update your income when you re-enroll. Advance credits are reconciled on your tax return, and if your actual income comes in higher than projected you may have to repay some or all of the credit.

Which states have different Marketplace deadlines for 2027?

States that run their own exchanges set their own windows; in the DMV, DC’s deadline is January 31, Maryland’s is January 15, and Virginia’s is January 29, 2027. Every state that uses HealthCare.gov follows the November 1, 2026 to January 15, 2027 schedule. In every state, enrolling by December 15 is the safe way to start coverage January 1.

2027 Marketplace open enrollment dates for state-run exchanges, as announced by each state exchange and compiled as of August 2026. DMV jurisdictions listed first. Deadlines can change; confirm on your state’s exchange before relying on a late date.

How do HMO, PPO, and metal-tier plans differ?

An HMO generally costs less but limits you to its network and requires referrals for specialists, while a PPO costs more and lets you see out-of-network providers at higher cost-sharing. The right one depends on whether your current doctors are in network and how much you value flexibility.

On the Marketplace, metal tiers describe how costs are split, not the quality of care:

• Bronze: lowest premiums, highest deductibles. Now HSA-compatible. Fits people who expect little care and hold enough cash to cover the deductible.
• Silver: a middle ground, and the only tier eligible for cost-sharing reductions if your income qualifies.
• Gold: higher premiums, lower deductibles. Fits households that expect significant care in 2027, such as a planned surgery or a birth.

Every ACA-compliant plan covers the same essential health benefits, including preventive care, maternity, mental health, and prescriptions.

What happens if you miss open enrollment?

If you miss the window, you generally can’t change coverage until next year unless you have a qualifying life event such as marriage, divorce, a birth or adoption, a move, or losing other coverage. Employer plans typically give you 30 days after the event to make changes; the Marketplace generally gives 60 days.

Without a qualifying event, your options narrow: keep your current coverage (most plans auto-renew), look at short-term plans (which may exclude pre-existing conditions and vary by state), or check Medicaid eligibility if your income has dropped. FSA elections are the strictest: miss them and you generally wait a full year.

How do open enrollment choices fit into your financial plan?

Open enrollment decisions belong inside your financial plan, not next to it, because the same choices affect your tax bracket, your cash reserves, your retirement savings rate, and your family’s protection if something goes wrong. A health plan that saves premium but leaves a $12,000 exposure changes how much cash you should hold. A dependent care FSA changes your take-home pay. A disability gap changes how much risk your whole plan can carry.

At District Capital Management, reviewing benefit elections each fall is part of our comprehensive financial planning engagement.