Take Command's 2027 Open Enrollment Guide + FAQs

Open Enrollment season is about to be upon us again, and if you ask anyone on our team, it might just be our favorite time of year. Most people don't share that level of excitement, and that's exactly why we built this guide. Whether you're shopping for individual health insurance for the first time or you've done this before and just want a refresher, consider this your go-to resource for navigating the season with confidence.

A quick note before we dive in: ICHRA has a new name. The Centers for Medicare & Medicaid Services (CMS) and the Small Business Administration (SBA) announced that ICHRA is now called CHOICE Arrangement, short for Custom Health Option and Individual Care Expense Arrangement. This is purely a name change for now. The rules, structure, and benefits work exactly the same as before. You'll still see plenty of people using "ICHRA," since that's what the industry has called it for years, so we'll use both terms throughout this guide to keep things clear.

This guide has been fully updated for the 2027 Open Enrollment season.

Here's what we'll cover:

• What Open Enrollment is and when it happens
• How to shop for and buy individual coverage

• How to renew or switch your existing plan

• What Premium Tax Credits are and how they work with your HRA
• Answers to the questions we hear most often

Section 1: Understanding Open Enrollment

What exactly is Open Enrollment?

Open Enrollment is the annual window when you're able to sign up for a health insurance plan. This year, that window runs from November 1, 2026 through January 15, 2027 across most of the country, matching the same general timeline used in previous years. There was some uncertainty earlier this year after a federal rule threatened to shorten the enrollment period and eliminate the February 1 coverage start option, but a federal judge struck that rule down in June 2026. The result is good news for shoppers: the familiar dates and flexibility are staying put for this cycle.

A handful of states manage their own exchanges and give residents extra time. If you live in California, Nevada, New Jersey, New York, Rhode Island, or Washington D.C., your deadline stretches to January 31, 2027. Massachusetts residents get until January 23, 2027. A few states move in the opposite direction and open earlier or close sooner, so it's always worth confirming your state's specific dates if you're not shopping on the federal exchange.

Timing also affects when your coverage actually kicks in. Enroll by December 15, 2026, and your plan begins January 1, 2027. Wait until after that but before the January 15 cutoff, and your coverage won't start until February 1, 2027 in most states.

If you're on Medicare, your calendar looks different entirely. Medicare's enrollment period runs October 15 through December 7, 2026, giving you a head start to review and adjust your coverage before it takes effect on January 1, 2027.

Why is Open Enrollment limited to specific dates?

It comes down to keeping the insurance pool balanced. Without set enrollment dates, people might wait to sign up until they're already sick, while healthy individuals skip coverage altogether. Insurers call this adverse selection, and it drives costs up for everyone. A defined enrollment period keeps the risk pool more predictable and, ultimately, more affordable.

Where can you buy individual insurance?

During Open Enrollment, insurance companies sell plans through what's commonly called the marketplace or exchange. These are known as on-exchange plans. In most states, that means Healthcare.gov, though California, New York, Pennsylvania, and a few others run their own state-based exchanges instead.

Here's something worth knowing: Healthcare.gov only shows you on-exchange plans, but insurers sell far more coverage off-exchange, directly through their own websites. That's a lot of options to sort through on your own. Take Command’s platform solves that by showing you every available plan side by side, on-exchange and off, so you can compare real prices and coverage details in one place. Look for plans tagged Easy Enroll. Those come with fast, simplified sign-up that our team manages for you, backed by direct support from the carrier itself.

What's the difference between "the marketplace" and "the exchange"?

They're the same thing. The Affordable Care Act established this online marketplace so individuals could shop for coverage and compare plans in one location, most commonly known as Healthcare.gov. It's also the only place where you can access premium subsidies and cost-sharing reductions, which makes it an important stop even if you end up buying off-exchange in the end.

Why is Open Enrollment significant for me?

If your employer has offered you a health reimbursement arrangement, this is your moment to lock in a 2027 plan that works with it. Mark December 15, 2026 on your calendar as the deadline for January 1 coverage, and remember that Open Enrollment stretches through January 15, 2027 for anyone enrolling later, with February 1 start dates.

The plan you choose needs to meet your HRA's requirements: a qualified health plan if you have a CHOICE Arrangement (formerly ICHRA), or a Minimum Essential Coverage plan if you have QSEHRA. Existing Take Command clients will find a personalized to-do list waiting on their dashboard. If you're new to the platform, our onboarding process walks you through shopping from start to finish. Keep an eye on your inbox in November for an email letting you know it's time to log in and get started.

Section 2: How To Buy Individual Insurance

Where do you even start?

Shopping for insurance can feel like a lot, especially if it's your first time. Before you open the portal, take a few minutes to think through what matters most for your situation this year. A few questions worth asking yourself:

• Would I rather pay a lower monthly premium or a lower deductible?

• Do I see a specialist regularly who needs to stay in-network?

• Are there prescriptions I need covered without interruption?

• Do I anticipate any major medical needs this year, like surgery, ongoing therapy, or a pregnancy?

The costs that should drive your decision are the predictable ones: prescriptions, regular doctor visits, therapy, and equipment. If you're generally healthy and don't expect much beyond routine care, that's useful information too. Things like catching a cold or spraining an ankle are unpredictable by nature, so they shouldn't be the deciding factor in which plan you pick.

Take Command’s shopping portal makes this easier by letting you search for your specific providers to confirm network status, and check whether your prescriptions appear in a plan's drug formulary before you commit.

How do you make sure you're not overpaying?

Here's some reassuring news. Pricing on any given plan is fixed by law, no matter where you buy it. A silver plan from Blue Cross Blue Shield costs exactly the same whether you purchase it through Healthcare.gov, directly from the insurer, or through a broker. Our portal reflects those same accurate prices across every option, so you're comparing real numbers from the start.

How can you tell if a plan qualifies for your HRA?

This is one of the most important questions to get right, since getting it wrong can mean losing out on tax-free reimbursement entirely.

Plans that work with CHOICE Arrangement (formerly ICHRA):

• Major medical plans purchased on the exchange (Bronze, Silver, and Gold) 
• Medicare, provided you have Part A and Part B together, or Part C
• Catastrophic plans, limited to those under 30 or who qualify for a hardship exemption
• Student Health Insurance

Plans that won't work include health sharing ministries, TRICARE, short-term or indemnity plans, and other employer-sponsored group coverage, whether through a spouse's job, COBRA, or a retirement plan.

Plans that work with QSEHRA:

• Major medical plans: Any ACA-compliant plan that qualifies as Minimum Essential Coverage. If you bought it through Healthcare.gov or your state marketplace, it qualifies for tax-free reimbursement.
• Student insurance
• A spouse's group plan, with some conditions: Only the portion your spouse's employer doesn't cover is eligible. Since most group premiums are already deducted pre-tax, your QSEHRA reimbursement may need to be treated as taxable to avoid double-dipping on tax benefits. If you can confirm your premium is paid post-tax, tax-free reimbursement is still possible.
• Government plans: Medicare, Medicaid, CHIP, TRICARE, and VA Care all count as Minimum Essential Coverage, and any premiums you pay out of pocket can be reimbursed tax-free.
• Dental and vision coverage: Individual premiums qualify for tax-free reimbursement. If your dental or vision coverage comes through a spouse's employer, only the unsubsidized portion applies.
• Limited benefit plans: Short-term, fixed indemnity, and accident plans can qualify for tax-free reimbursement, as long as you also carry Minimum Essential Coverage and the plan pays the provider directly rather than sending cash to you.

If all of this feels like a lot to track, here's the simplest takeaway: any plan purchased on the exchange automatically satisfies HRA compliance, and off-exchange major medical plans sold during Open Enrollment qualify too. And of course, our platform is built to guide you through every step of this decision.

Here is a post on plans that integrate with QSEHRA and plans that integrate with ICHRA to help you weigh your options.

What if you're on Medicare and have an HRA?

Good news here too. Medicare is reimbursable through your HRA, as long as you have Part A and Part B together, or Part C. Part B alone won't cut it.

We've teamed up with SmartConnect to make Medicare enrollment simple. It's a white-glove service that helps you find Medicare Advantage and Medicare Supplemental plans built to offset the deductibles, copays, and coinsurance that Medicare alone doesn't cover. Once you've chosen a plan, submit your proof of coverage along with receipts for eligible care to Take Command, and you'll be reimbursed tax-free.

Remember, Medicare's own enrollment window runs October 15 through December 7, 2026, so use that time to evaluate whether your current coverage still fits your needs.

What should you watch out for while shopping?

Being an informed shopper saves you headaches down the road. Our "Health Insurance 101" resource breaks down the terminology you'll run into, so jargon doesn't slow you down. If you're shopping outside an exchange, say through a broker, be cautious of plans labeled indemnity or short-term. These don't qualify for CHOICE Arrangement, and while some can be supplemented to work with QSEHRA, they won't satisfy CHOICE Arrangement requirements under any circumstances.

One more heads-up: if you're leaving a job and COBRA comes up as an option, think twice before defaulting to it. It's rarely the best deal financially. You could end up billed for up to 102% of your old plan's total cost, since that includes the full premium plus a 2% administrative fee.

Can you just keep your same plan?

If you liked your 2026 plan and it's being offered again for 2027, renewing is often straightforward. Take Command clients who had an Easy Enroll plan last year may see a renewal option waiting when they log in. That said, if anything has changed, like adding a dependent or moving to a new address, you'll likely need to shop again to intentionally re-select the same plan rather than assume it will carry over automatically.

Do you need to cancel your old plan?

Yes, and this step is easy to overlook. If you're switching insurance companies for 2027, call your old carrier and cancel before they auto-renew you and charge a January premium you don't need. Even if you're staying with the same company but switching plans, confirm they've removed the old plan from your file. Some carriers process payments mid-month, so canceling in early December gives you the safest buffer. Your 2026 plan stays active through the end of December regardless, with your new 2027 plan picking up right on January 1.

Section 3: Making Sense of Premium Tax Credits

Premium tax credits, often shortened to PTCs, are refundable subsidies designed to help eligible individuals and families afford Marketplace coverage. Qualifying for one depends on meeting a specific set of requirements.

Here's an important update for this year: the enhanced premium tax credits that expanded eligibility and increased subsidy amounts from 2021 through 2025 officially expired at the end of 2025. The core PTC program is still active and helping people afford coverage, but the income cap of 400% of the federal poverty level has returned for both 2026 and 2027, and subsidy amounts are generally smaller than what enrollees may have gotten used to. Because of this shift, it's worth checking your eligibility fresh this year rather than assuming last year's numbers still apply. Our shopping portal calculates this for you automatically based on your current income and household size.

How do you know if you qualify?

Tax credits are generally based on household size and income, and they can vary depending on where you live. You may qualify if you:

• Fall within the eligible income range
• Cannot be claimed as someone else's dependent
• Don't file taxes as Married Filing Separately
• Have coverage through the marketplace or exchange
• Can't access affordable coverage through an employer-sponsored plan that provides Minimum Essential Coverage
• Aren't eligible for a government program like Medicaid, Medicare, CHIP, or TRICARE
• Pay your share of premiums not covered by advance credit payments

How does your HRA interact with your tax credit?

This depends entirely on which HRA type you have.

QSEHRA: Think of it as trading one tax benefit for another. If your employer's QSEHRA allowance is smaller than the tax credit you'd otherwise qualify for, you can still access the difference. For example, a $500 available tax credit paired with a $400 QSEHRA allowance leaves you with a $100 PTC. One critical step here: notify your insurer about your QSEHRA benefit as soon as you enroll, since they'll need to recalculate your credit accordingly. Skip this step, and you risk having to repay credits to the IRS at tax time.

CHOICE Arrangement (formerly ICHRA): Unlike QSEHRA, this arrangement gives you the choice to opt out each year. Accept it, and you forfeit premium tax credits entirely for yourself and any dependents. Opt out, and the exchange will evaluate whether your employer's offer counts as affordable. If it's deemed unaffordable, you may still be able to claim tax credits. If it's considered affordable, you generally can't. When you enroll through the exchange, expect to be asked whether you're offered employer coverage, including a CHOICE Arrangement, so have that information ready.

Our onboarding team walks every client through these nuances, so you don't have to untangle it alone.

Also check out the following resources:

• More on QSEHRA & Premium Tax Credits
• More on ICHRA & Premium Tax Credits
• Affordability calculator (for employees)

Section 4: Everything Else You Might Be Wondering

On-exchange versus off-exchange, what's the real difference?

On-exchange plans are purchased through Healthcare.gov or a state-run exchange, and they're the only plans eligible for premium tax credits. Off-exchange plans are sold directly by insurers outside that system. Our portal displays both types side by side, so comparing your full range of options doesn't require jumping between websites.

What do the metal tiers actually mean?

Metal tiers signal how much of your care costs the plan covers, and how much lands on you.

• Bronze: Best suited for people who rarely need care beyond an annual checkup. Expect to cover about 40% of costs yourself, with the plan handling 60%.

• Silver: A middle ground for those managing a mild condition or occasional specialist visits. You'll typically pay 30% out of pocket, with 70% covered.

• Gold: Built for anyone managing a chronic condition or needing frequent care. Expect around 20% out of pocket, with 80% covered.

• Platinum: Designed for higher, more frequent medical needs. You'll pay roughly 10% out of pocket, with 90% covered by the plan.

Check out our blog post on what the metal tiers mean for more information.

What are premiums and deductibles, really?

Your premium is the fixed monthly cost of having coverage, and it's typically what your HRA allowance is meant to cover. Your deductible is the amount you're responsible for before your insurance starts contributing to costs. One detail that trips people up: your premium payments don't count toward your deductible at all.

HMO, PPO, EPO, POS: how do these networks differ?

• HMO: The most budget-friendly option, though also the most restrictive. You'll need a designated primary care physician and referrals for specialist visits, and your network is usually local.

• PPO: The most flexible choice, and typically the priciest. No referrals required, and you can access in-network providers even out of state.

• EPO: A middle-ground option, more flexible than an HMO and usually cheaper than a PPO. Referrals aren't required, but stepping outside the network means paying full cost.

• POS: Another hybrid model. It requires referrals like an HMO but allows out-of-network access at a higher cost, similar to a PPO.

Can you switch plans outside of Open Enrollment?

Generally, no. On-exchange plans can only be purchased or changed during Open Enrollment itself, unless a qualifying life event triggers a Special Enrollment Period. Having a baby, getting married, getting divorced, or changing jobs all count. If your employer offers you an HRA for the first time, that also opens a Special Enrollment Period, giving you 60 days to select a compliant plan.

What about dental coverage? 

You've got two paths here. Some marketplace plans bundle dental coverage right into your medical plan, which you can spot easily while comparing options on our portal. If your plan doesn't include it, you can add a standalone dental plan with its own separate premium. For our clients, we recommend individual dental coverage through Renaissance and AmFirst, both of which pair well with HRA benefits.

Here's a helpful post for more information about our dental partnerships.

Ready to get started?

This season brings a lot of decisions, and we're glad to be part of the process alongside you. Questions along the way are completely normal, so reach out anytime you need support. When you're ready to shop, log in to our portal and we'll guide you through every step, start to finish.

Happy Open Enrollment!