Sometimes. Whether you can buy health insurance right now depends largely on the type of coverage you’re looking for.

If you’ve been asking yourself “can I buy health insurance anytime?” the honest answer is: it depends. ACA Marketplace plans are generally sold during a set Open Enrollment window each year, unless you qualify for a Special Enrollment Period. Medicaid and CHIP work differently. They accept applications year-round. COBRA has its own separate timeline, tied to your old job. And some private, medically underwritten health insurance options may accept applications any time of year. That depends on your state, the carrier, your health, and what’s actually available where you live.

None of that means every option is available to everyone, or that “you can apply anytime” means “you’re guaranteed to get approved.” It just means the calendar isn’t the only thing standing between you and coverage. Let’s walk through exactly how each path works, so you know which one actually applies to you.

We’re 1099 Health Insurance Solutions, a licensed agency based in Phoenix, Arizona, working with self-employed people, 1099 contractors, and small business owners in almost 30 states. This is the exact question we get asked most often, usually from someone who needs coverage now and doesn’t want to wait months for an answer.

On this page: When is Open Enrollment? · What is a Special Enrollment Period? · What qualifies you for one? · Missed Open Enrollment? · Private health insurance anytime? · Self-employed? · Lost your job? · COBRA to private? · Marketplace vs. private, compared · Need coverage right now? · Questions to ask · FAQ

When Is Open Enrollment for Health Insurance?

Open Enrollment is the one guaranteed window every year when anyone can sign up for an ACA Marketplace plan, no qualifying event required.

For the 2027 plan year, the federal Marketplace (HealthCare.gov) runs Open Enrollment from November 1, 2026 through January 15, 2027. If you want coverage starting January 1, you’ll generally need to enroll by December 15, 2026. Enroll after that, and your coverage typically starts a bit later, but you can still usually enroll through January 15.

Here’s a detail people miss: not every state uses those exact dates. States that run their own Marketplace can set a longer window. As of this writing, California, New Jersey, New York, and Washington D.C. extend into late January. Massachusetts and Virginia run into late January too. A couple of states even start earlier, in the fall. Not sure which kind of Marketplace your state uses? Check your state’s exchange directly. Federal deadlines don’t automatically apply everywhere. For a full walkthrough of last year’s dates and how this all works, see our Open Enrollment dates guide. Always confirm current-year dates, since these shift slightly year to year.

Open Enrollment is specific to ACA Marketplace plans. It has nothing to do with when you can apply for Medicaid, CHIP, or most private insurance products, which we’ll get into below.

What Is a Special Enrollment Period?

A Special Enrollment Period, or SEP, is a window outside of Open Enrollment when you’re allowed to sign up for a Marketplace plan. You don’t get one just by asking. It’s triggered by a specific event in your life, called a qualifying life event.

Here’s the general rule: once you experience a qualifying event, you typically get 60 days to enroll in a Marketplace plan. That window can start before the event too, in some cases, like if you know your coverage is ending in the next 60 days. Miss that 60-day window, and you’re generally back to waiting for the next Open Enrollment period.

The exact rules depend on which qualifying event applies to you, which is why it’s worth checking HealthCare.gov’s official list of qualifying events for your specific situation, or having someone check it with you.

What Qualifies You for a Special Enrollment Period?

Common qualifying events include:

• Losing job-based health coverage, including being laid off, fired, or having your hours cut below eligibility.
• Losing coverage through a spouse’s job, for the same reasons.
• Turning 26 and aging off a parent’s health plan.
• Getting married.
• Divorce or legal separation, if it results in you actually losing health coverage.
• Having a baby, adopting a child, or placing a child for foster care.
• Certain permanent moves, like relocating to a new state or county where your old plan isn’t available, as long as you had coverage before the move.
• Losing Medicaid or CHIP eligibility.
• COBRA running out on its own, once it reaches the end of its maximum coverage period.

Here’s the part that surprises a lot of people: voluntarily canceling coverage, or simply deciding your current plan costs too much, generally does not create a Special Enrollment Period. The event has to be something that happened to your coverage. A layoff counts. Your COBRA maximum period ending counts. Choosing to walk away from coverage that was still available to you usually doesn’t. We’ll go deeper on exactly how this plays out with COBRA a little further down, because it trips up more people than any other rule on this list.

Can You Get Health Insurance If You Missed Open Enrollment?

Missing Open Enrollment isn’t the dead end it feels like. Health insurance after Open Enrollment is still possible, in a few different forms. Here are your real paths forward, in order:

1. Check whether you qualify for a Special Enrollment Period. Go through the qualifying events above. If something on that list happened to you recently, or is about to, you may still be able to get a Marketplace plan right now.
2. Check whether you or your household qualify for Medicaid or CHIP. Unlike the Marketplace, Medicaid and CHIP accept applications any time of year, with no Open Enrollment window at all. It costs nothing to check.
3. Look into legitimate private or off-Marketplace options available in your state. Some private health insurance products accept applications year-round. We cover exactly how these work, and their real tradeoffs, in the next section.
4. Consider other limited or temporary alternatives carefully. Some short-term or supplemental options exist outside these categories too. Just go in with clear eyes: they may not offer the same protections, coverage, or pre-existing condition rules as ACA-compliant major medical insurance. Read the fine print, or have someone read it with you, before you buy.

Can You Buy Private Health Insurance Anytime?

This is where things open up. If you want to buy health insurance outside Open Enrollment, private plans are often the piece people haven’t heard about.

Here’s the part worth understanding clearly. “Open Enrollment” and “Special Enrollment Period” aren’t universal insurance concepts. They’re specific rules built into ACA Marketplace plans and employer group plans. Most private, non-ACA health insurance products were never built around that system in the first place. That’s why many of them, including most short-term health plans and other private, medically underwritten products, are typically available to apply for any time of year. There’s usually no calendar window to wait for, and no annual deadline to miss.

That doesn’t mean the door is wide open with no conditions attached. Many of these private plans use medical underwriting instead of a calendar restriction. In plain terms, that means the insurance company can ask you health questions on the application. Your eligibility, and sometimes your price, can depend on your medical history. Depending on the specific product, carrier, and state you’re in, that can mean anything from a quick health questionnaire to a more detailed review. In other words: the timing restriction goes away, but it’s replaced by a health-based one.

This part is genuinely important. Being available to apply year-round does not mean everyone who applies gets approved. It also doesn’t mean every year-round option is ACA-compliant major medical coverage. Those are two separate questions. A plan can be legally sold in your state, and still turn down an applicant, limit what it covers, or exclude a pre-existing condition.

That’s exactly why this decision depends heavily on your own health situation:

• If you have significant ongoing medical needs, expensive prescriptions, a pregnancy, or a pre-existing condition, you’re often better served by evaluating ACA-compliant coverage first. Marketplace plans, by law, cannot deny you coverage or charge you more because of your health history. That protection matters a lot if you have real medical needs.
• If you’re generally healthy, this may be worth a closer look, especially if you don’t qualify for meaningful ACA premium subsidies. It can be worth comparing legitimate private options against what a full-price Marketplace plan would cost you. Neither one is automatically the better or cheaper choice. It depends on your health, your budget, and what each specific plan actually covers.

Don’t assume every private plan is a PPO, an HMO, or any particular network type. Products vary a lot by carrier and state, so it’s worth confirming the actual plan type, not just assuming based on the marketing.

Can Self-Employed People Buy Health Insurance Anytime?

This is one of the most common questions we get, so let’s be direct about it: being self-employed does not, by itself, create a Special Enrollment Period for Marketplace coverage. Freelancers, 1099 contractors, LLC owners, realtors, consultants, owner-operators, and other self-employed professionals all follow the same Marketplace enrollment rules as anyone else. Self-employment isn’t a qualifying life event on its own. Can self-employed people buy health insurance anytime? Only in the sense that everyone can: through Open Enrollment, a real qualifying event, Medicaid or CHIP, or a private option where one legitimately exists.

What self-employed people can do is look at every option actually available to them, the same way anyone else would. That means checking:

• Marketplace coverage, if you’re inside Open Enrollment or you have a genuine qualifying event.
• Medicaid or CHIP, if your household qualifies, any time of year.
• Private or off-Marketplace options, where legitimately available in your state, keeping the medical underwriting realities from the section above in mind.

This is exactly the situation 1099 Health Insurance Solutions works in every day. We’re not tied to a single carrier or a single kind of plan. That means we help self-employed people compare what’s actually available to them right now, instead of assuming the calendar has already closed every door.

Want more background on building the right coverage strategy as a self-employed worker? Our guide to health insurance for self-employed workers is a good starting point. And don’t forget: a portion of what you pay may be tax-deductible. We cover that separately in our guide to the self-employed health insurance deduction.

Can I Get Health Insurance After Losing My Job?

Yes, in most cases, and this is one of the clearest qualifying events there is. Losing job-based health coverage, whether through a layoff, a firing, or reduced hours, generally opens up a Special Enrollment Period.

Speed matters here. That 60-day clock starts running, and letting it slip by is one of the most common, and most avoidable, ways people end up without coverage. Once you’ve lost job-based coverage, you generally have three paths worth comparing:

• Marketplace coverage, using your new Special Enrollment Period.
• COBRA, continuing your old employer’s plan yourself, usually at full price plus a small fee.
• Other private coverage, where legitimately available and appropriate for your health situation.

These three options can look very different in cost and coverage side by side. We’ve broken that comparison down in detail in COBRA vs. Private Health Insurance: Which Is Better?, which is worth reading before you default to whichever option your old employer’s paperwork happens to mention first.

Can You Switch From COBRA to Private Health Insurance?

Yes, but the timing rules depend on exactly what kind of coverage you’re switching to, and this is where a lot of confusion happens.

There are three separate things at play here: COBRA itself, ACA Marketplace coverage, and private or off-Marketplace coverage. Each has its own enrollment rules, and they don’t automatically sync up with each other.

Here’s the rule that catches people off guard: voluntarily dropping COBRA before it runs out on its own generally does not create a Marketplace Special Enrollment Period. HealthCare.gov is direct about this. If you voluntarily drop COBRA, or simply stop paying the premium, you typically don’t get a new SEP. You’d need to wait for the next Open Enrollment period instead. The SEP only kicks in when COBRA runs out on its own, at the end of its maximum coverage period. A few other involuntary situations count too, like a former employer’s temporary premium subsidy running out.

This is exactly why it pays to plan ahead rather than react. If your COBRA is approaching its end date, start comparing your Marketplace, private, and continued-COBRA options before coverage actually runs out, not after. We’ve covered this timeline in more depth in How Long Can You Stay on COBRA? and in our broader COBRA alternatives guide, which walks through what actually happens once your COBRA coverage window closes.

ACA Marketplace vs. Private Health Insurance Outside Open Enrollment

Here’s a side-by-side look at how these two paths generally differ. Remember that private/off-Marketplace products vary quite a bit by carrier and state, so treat this as a general pattern, not a guarantee for every specific plan.

Feature	ACA Marketplace	Private / Off-Marketplace Options
Enrollment timing	Open Enrollment, or a qualifying Special Enrollment Period	Typically year-round for most products, since enrollment periods are an ACA/employer-plan rule, not a private-insurance one
Special Enrollment Period required?	Yes, outside Open Enrollment	No, most private products don’t use this system at all; a few carrier- or state-specific exceptions can still apply
Medical underwriting	Not allowed	Common, depending on the specific product and carrier
Pre-existing condition protections	Guaranteed by law	Varies by product; not guaranteed unless the specific plan says so
Premium subsidies	Available if you qualify, based on income	Not available; these aren’t ACA subsidy-eligible plans
Provider networks	Varies by plan (PPO, HMO, EPO, and more)	Varies widely by carrier and product; don’t assume a specific network type
Eligibility	Guaranteed issue during your enrollment window	May depend on health history, application answers, and underwriting
Best reason to investigate	You have real medical needs, want subsidy eligibility, or need guaranteed acceptance	You’re generally healthy, missed your enrollment window, or don’t qualify for meaningful subsidies

What If I Need Health Insurance Right Now?

So, can you get health insurance anytime you need it, no matter what? Not quite, but you have more paths than you’d think. If you need coverage urgently, here’s a simple way to think through it:

Do you have a qualifying life event? Check your Special Enrollment Period eligibility first. This is the fastest path to full ACA-compliant coverage outside Open Enrollment.

No qualifying event, but income is limited? Check whether your household could qualify for Medicaid or CHIP. Enrollment is available year-round, and it costs nothing to find out.

No qualifying event, and you don’t qualify for Medicaid or CHIP? This is when it’s worth investigating legitimate private or off-Marketplace options available in your state, understanding the medical underwriting realities covered above.

Do you have significant ongoing medical conditions, expensive prescriptions, a pregnancy, or planned medical treatment coming up? Slow down here, specifically. Pay close attention to ACA protections, plan exclusions, prescription formularies, provider networks, and pre-existing condition rules before choosing an alternative to Marketplace coverage. This is the situation where the difference between plan types matters the most.

Whatever your situation, compare more than one option before you buy. The first plan you find isn’t necessarily the right one. A quick side-by-side look at cost, network, and coverage can save you from a bad surprise later.

Questions to Ask Before Buying Health Insurance Outside Open Enrollment

Before you sign up for anything outside of standard Open Enrollment, get clear answers to these:

• Is this ACA-compliant major medical insurance, or something else?
• Does this plan use medical underwriting?
• Are pre-existing conditions covered, and if so, from day one or after a waiting period?
• What is the deductible?
• What is the maximum amount I could pay out of pocket in a bad year?
• Is this a PPO, HMO, EPO, or some other network type?
• Are my current doctors and hospitals actually in-network?
• Are my current prescriptions covered, and at what cost?
• Are there any benefit caps or major exclusions I should know about?
• Is the policy guaranteed renewable, or can it be canceled or non-renewed later?
• When does coverage actually become effective?
• Does this plan work if I travel, whether for work or personal reasons?
• What happens if I develop a serious medical condition after I’ve already enrolled?

If an agent or a website can’t answer these clearly, that’s worth treating as a red flag on its own.

Frequently Asked Questions

Can I buy health insurance anytime? Sometimes. It depends on the type of coverage. Marketplace plans generally require Open Enrollment or a qualifying Special Enrollment Period. Medicaid and CHIP accept applications year-round. Some private, medically underwritten plans may also accept applications year-round, depending on your state, health, and the specific carrier.

Can I get health insurance outside Open Enrollment? Yes, if you qualify for a Special Enrollment Period due to a life event like losing job-based coverage, having a baby, or getting married. Outside of that, Medicaid, CHIP, and certain private options may still be available depending on your situation.

What happens if I missed Open Enrollment? Check whether you qualify for a Special Enrollment Period first. If not, look into Medicaid or CHIP eligibility, and then legitimate private or off-Marketplace options available in your state. You’ll generally need to wait for the next Open Enrollment period for a new Marketplace plan otherwise. Most private plans enroll anytime. Check with a licensed advisor.

What qualifies for a Special Enrollment Period? Common qualifying events include losing job-based coverage, losing coverage through a spouse, and turning 26 off a parent’s plan. Marriage counts too, as does a divorce that results in lost coverage. So does having or adopting a child, certain permanent moves, losing Medicaid or CHIP eligibility, and COBRA running out at the end of its maximum coverage period.

How long do I have to enroll after losing health insurance? Typically 60 days from the date you lose coverage, though the exact window can depend on the specific qualifying event. Missing that window usually means waiting for the next Open Enrollment period.

Can I buy private health insurance outside Open Enrollment? Often, yes. Many private and off-Marketplace health insurance products accept applications year-round. Availability, eligibility, and pricing can depend on your state, the carrier, and your health history through medical underwriting. This isn’t guaranteed acceptance, and not every private option is ACA-compliant major medical coverage.

Can self-employed people get health insurance year-round? Being self-employed doesn’t create a Special Enrollment Period on its own. But self-employed people can check Marketplace eligibility, Medicaid or CHIP eligibility, and legitimate private options available in their state, the same as anyone else.

Can I get health insurance immediately? It depends on the type of coverage and your situation. Medicaid or CHIP, if you qualify, can move quickly. Some private options can also move fast if you qualify for the plan and pass any required underwriting. A Marketplace plan generally has a small delay before your effective date, even with a Special Enrollment Period.

Can I get health insurance after quitting my job? Yes, in most cases. Voluntarily leaving a job that offered you health coverage typically still counts as losing job-based coverage, which usually opens a Special Enrollment Period. COBRA is also usually an option if your former employer had 20 or more employees.

Can I switch from COBRA to another health insurance plan? Yes, but the timing depends on which plan you’re switching to. Switching to Marketplace coverage before COBRA naturally ends generally requires a qualifying event, since voluntarily dropping COBRA early doesn’t create its own Special Enrollment Period. Switching to a private, non-Marketplace plan may follow different rules, since many of those accept applications year-round.

Can I buy a PPO plan outside Open Enrollment? It depends on whether you mean a Marketplace PPO or a private one. A Marketplace PPO generally still requires Open Enrollment or a Special Enrollment Period. Some private carriers offer PPO-style plans that may accept applications outside that window, subject to medical underwriting and availability in your state.

We Can Help You Sort Out What’s Actually Available to You

If you’re unsure whether you have to wait for Open Enrollment, we can help you compare the options that may be available based on your situation, state, health needs, and budget.

1099 Health Insurance Solutions specializes in helping self-employed individuals, independent contractors, families, and small business owners understand their real health insurance options. That could be a Marketplace plan, COBRA, or a private alternative. We can’t promise savings, approval, or eligibility for any specific plan, since that depends on your own situation and the carrier’s rules. What we can do is walk through what’s realistically available to you right now.

Schedule a free 15-minute discovery call to talk through your options, or get a free quote if you already know what you’re looking for.

This article is for general information only. It isn’t medical, legal, or tax advice. Enrollment rules, deadlines, and product availability change and vary by state and carrier. Confirm current details with HealthCare.gov, your state’s Marketplace, or a licensed agent before making a decision.

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Sources used in this article: HealthCare.gov — Getting Health Coverage Outside Open Enrollment, HealthCare.gov — Special Enrollment Period Qualifying Events, HealthCare.gov — COBRA Coverage, HealthCare.gov — Medicaid and CHIP Coverage, U.S. Department of Labor — COBRA Continuation Coverage FAQs, CMS — Understanding COBRA, KFF — COBRA and Marketplace Subsidy Eligibility FAQ.