You've just landed a new job—congratulations! But there's a catch: your new employer's health insurance doesn't kick in for 60 days. Or maybe you're between jobs entirely, wondering how you'll afford coverage until your next role starts. Here's the thing most people don't realize: losing job-based health insurance actually unlocks special options you can't access during regular enrollment periods. And if you play your cards right, you might avoid paying for gap coverage altogether.
The average person switching jobs faces a 30 to 90-day waiting period before new coverage begins. During that window, you're on your own. But you're not without options. Whether you choose COBRA, marketplace coverage, or short-term insurance depends on your health needs, budget, and how long you'll be uninsured. Let's break down exactly what each option costs, covers, and when it makes sense.
Understanding Your 60-Day Special Enrollment Window
The moment you lose job-based health insurance, the clock starts ticking on your special enrollment period. You have 60 days before or after your coverage ends to enroll in a marketplace plan through Healthcare.gov. This isn't like open enrollment where you're stuck with whatever you chose for the whole year—losing coverage is what insurance calls a "qualifying life event," and it opens up all the same plan options you'd see in November.
Here's what makes this powerful: if you know your last day of coverage in advance, you can apply up to 60 days early. Your new marketplace coverage can start the first day of the month after you lose your job-based plan. That means if you're leaving a job on March 15th and your employer coverage ends March 31st, you can sign up for a marketplace plan in February that starts April 1st. Zero gap.
You'll need documentation proving you lost coverage—usually a letter from your former employer or your final pay stub showing your last date. The marketplace gives you 30 days after selecting a plan to submit this proof. Don't skip this step. Without it, your enrollment gets canceled and you're back to square one.
COBRA: Expensive But Retroactive
COBRA lets you keep your exact same employer health plan for up to 18 months after you leave. Same doctors, same prescription coverage, same deductible that might already be partially met. The catch? You pay the full premium your employer was covering, plus a 2% administration fee. For 2025, that averages around $584 per month for individual coverage, or $1,200 to $2,000 for family plans.
But here's the COBRA trick nobody tells you about: you have 60 days to decide whether to elect coverage, and if you do sign up, it's retroactive to your last day of employer coverage. Let's say you leave your job on January 15th. You could wait until March 14th—almost two full months—to elect COBRA. If you stayed healthy and didn't need a doctor, you saved two months of premiums. But if you broke your ankle on February 20th, you can still elect COBRA on March 1st, pay the retroactive premiums for January and February, and have that emergency room visit covered.
This retroactive feature is both COBRA's biggest advantage and its biggest risk. If you're gambling on staying healthy and something happens, you're covered. But you'll owe all those back premiums in one lump sum—plus you typically have 45 days after electing to make that initial payment. For a family, that could mean writing a $4,000 check to bring your account current.
COBRA makes the most sense if you're mid-treatment for something serious, you've already met a significant portion of your deductible, or you're only a few weeks away from new employer coverage starting. For a routine 30-day gap, it's usually overkill.
Marketplace Plans: Often Cheaper With Subsidies
If COBRA seems outrageously expensive, marketplace plans through Healthcare.gov are usually your best bet. About 80% of people who buy marketplace coverage qualify for premium subsidies based on income. These aren't loans or credits you pay back—they're discounts applied directly to your monthly premium. If you're between jobs and your income for the year is low, you might qualify for significant savings.
Marketplace plans must cover the Affordable Care Act's essential health benefits, including pre-existing conditions, preventive care, prescription drugs, and maternity care. You'll choose from Bronze, Silver, Gold, or Platinum tiers based on how much you want to pay monthly versus when you use care. Bronze plans have the lowest premiums but highest deductibles—fine for catastrophic coverage. Silver plans unlock additional cost-sharing reductions if you qualify based on income.
The downside? Your new marketplace plan comes with a fresh deductible and out-of-pocket maximum. If you'd already met $3,000 of your old employer plan's $5,000 deductible, that progress doesn't transfer. You're starting over. And unlike COBRA, marketplace coverage isn't retroactive. It starts on a future date, so any gap between your old employer plan ending and your new marketplace plan beginning is on you.
Short-Term Insurance: Cheap But Limited
Short-term health insurance costs as little as $85 per month and can start as soon as the next day after you apply. It's designed exactly for this situation: temporary gaps between major medical plans. But starting September 2024, federal regulations limited these plans to a maximum of four months of coverage, down from the previous 12 months some states allowed.
Here's what you're giving up for that low premium: short-term plans can exclude pre-existing conditions entirely, don't have to cover prescription drugs or maternity care, and often come with high deductibles and limited networks. If you take medication for diabetes, have a history of cancer, or could become pregnant, these plans won't help you. They're catastrophic coverage for healthy people who need a bridge to the next job—nothing more.
Some insurers have found workarounds to the four-month limit by offering sequential policies from different carriers, potentially giving you up to 12 months of coverage. But read the fine print. Each new policy can re-underwrite your health status and deny coverage if something developed during the previous short-term policy.
How to Negotiate Coverage at Your New Job
Before you resign yourself to paying for gap coverage, ask your new employer about their benefits waiting period. The standard is 30 to 90 days from your start date, but many companies will waive it if you ask—especially for hard-to-fill positions or senior roles. The worst they can say is no.
If they won't budge on the waiting period, ask if they'll cover your COBRA premiums during the gap. Some employers build this into relocation packages or signing bonuses for exactly this reason. Even if it's not standard, HR might have the flexibility to approve it for the right candidate. Frame it as a retention issue—you're more likely to accept the offer and start on their preferred date if you're not worried about a coverage gap.
You can also negotiate your start date. If your new employer wants you to begin April 1st but their benefits don't start until day 60, ask to start June 1st instead so you can time your departure from your old job to minimize the gap. Most hiring managers would rather wait an extra month than lose a good candidate over insurance timing.
The Real Cost of Coverage Gaps
Some people try to skip insurance entirely for a month or two between jobs. After all, what are the odds something happens in 60 days? But consider this: a broken arm costs about $2,500 to treat. An appendectomy runs $15,000 to $35,000. A three-day hospital stay for pneumonia can hit $30,000. Even healthy people in their 30s can face financial catastrophe from one bad day.
There's also a paperwork risk. If you go uninsured for more than 63 days in some states, future insurers can impose pre-existing condition exclusions on certain employer plans. Federal law protects you from this on marketplace and most employer plans now, but some grandfathered plans still have these provisions. Don't assume you're safe just because you're young and healthy.
Your Step-by-Step Action Plan
As soon as you know you're leaving a job, get your current plan's Summary of Benefits and Coverage. You'll need this to compare COBRA to marketplace options. Note your deductible progress, remaining out-of-pocket maximum, and any ongoing treatments that require specific providers or medications.
Next, ask your new employer these three questions: When does health insurance begin? Can the waiting period be waived? Will you cover gap coverage costs? Get the answers in writing as part of your offer letter if possible. Then visit Healthcare.gov and run the numbers. Enter your expected income for the full year—not just while you're unemployed—to see what subsidies you might qualify for. Compare the monthly premiums and deductibles to your COBRA cost.
If you're healthy, have minimal prescriptions, and are only looking at a 30-day gap, short-term insurance might save you hundreds of dollars. If you have ongoing treatment or take regular medications, stick with COBRA or a marketplace plan. And if you're genuinely between jobs with no immediate offer, marketplace coverage with subsidies is almost always cheaper than COBRA unless you're very close to meeting a large deductible.
Losing health insurance feels scary, but you have more control than you think. Use that 60-day window strategically, negotiate with your new employer, and choose coverage that matches both your health needs and your budget. The worst decision is no decision—don't let a short gap in employment turn into a long-term financial problem.
