Lost Your Employer Health Insurance? A First-Week Checklist

To see what keeping your old plan would cost, try the COBRA cost calculator. It also gives you your 60-day Marketplace deadline.

Step 1: Get the exact end date in writing

Before anything else, find out the last day your medical coverage is in force. Many employer plans run through the end of the month in which you leave, but some stop on your last day of work, and a severance agreement can keep coverage going longer. Do not guess. Every deadline in this guide is measured from that date.

Ask HR, or the benefits administrator, for these in writing:

• The end date for medical, dental and vision coverage, which are not always the same.
• Whether your severance includes any months of COBRA paid by the company.
• When the COBRA election notice will be sent, and what the monthly COBRA premium will be for each person covered.
• What happens to a flexible spending account balance. A health FSA usually ends with the job, so spend what is left before coverage ends, or ask whether there is a period to submit claims afterward.

A health savings account is different. The money in an HSA is yours and stays with you after the job ends.

Step 2: Take care of prescriptions and ongoing care

While the old plan is still active, use it:

• Refill prescriptions you take regularly, and ask whether the plan allows a 90-day supply.
• Keep appointments you already have, and ask your doctor's office whether anything scheduled after the end date can be moved up.
• Make a list of every doctor, hospital and medication, with doses. You will need it to check networks and drug lists on any new plan.
• Note any prior authorizations for medications or procedures. They do not carry over to a new insurer, so plan time to redo them.

If anyone in the family is pregnant, in active treatment or scheduled for surgery, put that at the top of the list. It shapes everything that follows, because those situations favor coverage that accepts everyone.

Step 3: Understand the COBRA election window and the real price

COBRA lets you keep the same employer plan for a limited time, usually up to 18 months, at the full cost. Federal COBRA applies to employers with 20 or more employees. Smaller employers may be covered by a state continuation law instead, and those rules differ; the COBRA alternatives page has each state's version.

How the timing works:

• The notice can take a few weeks to arrive. The employer and the plan administrator each have time to process it.
• You have 60 days to elect, counted from the later of the date coverage ends or the date of the notice.
• Coverage is retroactive to the day after the old coverage ended, as long as you elect and pay.
• The first payment is due within 45 days of electing, and it must cover every month back to the end date. Monthly payments follow, with a short grace period.

The price is where most people stop. Under COBRA you pay the whole premium, both your old share and the larger share your employer used to pay, plus up to 2 percent for administration. For family coverage, that is often the biggest bill of the month. Look at the actual number before you assume COBRA is your plan. If you are leaving to work for yourself, the self-employed vs COBRA comparison lays out that choice in detail.

Step 4: Mark the 60-day Marketplace deadline

Losing job-based coverage opens a special enrollment period on the Marketplace. You can choose a plan up to 60 days before your coverage ends and up to 60 days after. If you pick a plan before the old one ends, the new plan can start the first day of the next month with no gap. If you pick one after, coverage starts the first of the month after you choose, so waiting costs you covered months.

Three rules that catch people:

• Being offered COBRA does not block a tax credit. Enrolling in COBRA does, for the months you are on it.
• Dropping COBRA later on your own does not reopen the Marketplace. If you elect COBRA and change your mind while your original 60-day window is still open, you can usually still switch. After the window closes, you generally wait for open enrollment.
• Open enrollment may overlap. For 2027 coverage it runs November 1, 2026 through January 15, 2027 on HealthCare.gov, and you need to choose by December 15 for a January 1 start.

The special enrollment guide explains start dates and the documents HealthCare.gov may ask for, and the enrollment checker gives you a quick answer for your own dates.

Step 5: Work out your income for the rest of the year

The Marketplace tax credit is based on household income for the whole calendar year, not on what you earn from here forward. That surprises a lot of people who just lost a paycheck. Count:

• Wages you have already earned this year.
• Severance and any payout for unused vacation.
• Unemployment benefits, which count as income for the credit.
• What you expect to earn at a new job or from freelance work.
• A spouse's income and any investment or retirement withdrawals.

Picture a single project manager laid off in June 2026 after earning $58,000 so far. With $10,000 of severance, her year is already at $68,000 before any new job. That is above the $62,600 line for 2026 coverage, so a Marketplace plan for the rest of 2026 would cost full price. If she expects to earn less in 2027, her picture for January could be very different. For 2027 coverage, the line is $63,840 for one person and $132,000 for a family of four.

Estimate carefully. Starting with the 2026 tax year there is no cap on paying back excess credit, so an estimate that is too low can turn into a tax bill. When you land a new job, update your application, and remember that an offer of affordable job-based coverage generally ends the credit. The guide to paying back the credit covers reconciliation.

Step 6: Price a private plan

Private, medically underwritten plans do not use enrollment windows. You can apply any day, approval depends on your health answers, and if you are approved, some plans can start shortly after approval. They are priced on age, zip code and health rather than income, so severance or a strong first half of the year does not change the premium. Benefits vary by plan, so I go through the plan documents with you before you apply.

Timing matters here. Apply early in your 60 days. If the application is approved, you have a choice. If it is declined, you still have time to use the Marketplace window, and COBRA's retroactive election is still there as a backstop. People who wait until day 55 lose that cushion.

Step 7: Sort out your spouse and children

If your spouse has a job with benefits, check that plan right away. Losing your coverage usually gives you a right to join a spouse's employer plan, but the deadline is set by that plan and is often only 30 days. That can be the shortest clock in this whole checklist. Ask your spouse's HR department for the exact date.

Compare the family options side by side. Your spouse's employer family rate is not automatically the cheapest choice. Since 2023, the Marketplace judges whether employer family coverage is affordable based on the cost of covering the whole family. For 2027, if the employee's share for family coverage is more than 10.22 percent of household income, the rest of the family may qualify for a Marketplace credit while your spouse stays on the employer plan.

Each family member can make a separate COBRA choice. A child in the middle of treatment can stay on COBRA while the rest of the household moves to other coverage. Children can stay on a parent's Marketplace or employer plan until 26. The family health insurance guide covers how to split a household across plans.

What not to do

• Do not let coverage lapse while you sort things out. A gap leaves you exposed, and if you miss the 60 days, the Marketplace door closes until open enrollment.
• Do not drop COBRA early without a plan in place. Make sure the new coverage is approved and has a start date first, because a voluntary drop does not open a new window.
• Do not wait for the COBRA notice to start comparing. The Marketplace clock is running from the day coverage ends.
• Do not base your income estimate on last year's W-2. Use this year's actual and expected income, severance included.
• Do not skip the first premium. Neither COBRA nor a new plan is in force until it is paid.
• Do not assume a new job's coverage starts on day one. Waiting periods of up to 90 days are common, and you need coverage for that stretch too.

The week on one page

1. Get the coverage end date and the COBRA premium in writing.
2. Refill prescriptions and list your doctors and medications.
3. Put the COBRA deadline and the Marketplace deadline on your calendar.
4. Estimate household income for the full calendar year.
5. Check your spouse's employer plan and its deadline.
6. Get a Marketplace quote with your real credit and a private quote side by side.
7. Decide, enroll and pay the first premium before the old coverage ends if you can.

Where I fit

I am an independent broker licensed in 31 states, including Florida, Texas and North Carolina. I put COBRA, the Marketplace with your actual credit and private plans priced on your health next to each other, and tell you which one I would choose in your place. There is no fee to you, and if COBRA is the right answer, I will say so. Start a quote or call (786) 218-2384. For a shorter overview, see the between jobs guide.