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Part 8: Health Insurance

Losing a job usually means losing the health plan that came with it, on a date the employer sets. Get that date in writing, as Part 2 directed. Four doors can replace the coverage. They have different clocks, different costs, and different fine print, and two of them close fast. Worksheet 4, Health Coverage Comparison, is built to put the four side by side before you choose.

Door 1: COBRA, keeping the plan you had

COBRA is a federal law that lets you keep your employer's group health plan for a limited time after you lose it, by paying the premium yourself. The mechanics, from the U.S. Department of Labor:

• Who it covers. COBRA generally applies to private-sector group health plans of employers with at least 20 employees, counted as the DOL guide specifies, on more than half of their typical business days in the previous calendar year. It also covers state and local government plans. It does not apply to federal government plans or to certain church plans. If your employer was smaller, ask your state insurance department about state continuation rules, which many states have. Your state sets those, so the answer lives with the state.
• The election window. The plan must give you at least 60 days to elect COBRA. That period runs from the later of the date you would lose coverage or the date the plan sends your election notice, and the notice itself will state your dates. Use the notice's dates over any summary, including this one.
• Retroactive coverage. If you elect within your window, coverage is retroactive to the date you lost it. There is no gap on paper. There is also no discount for the wait: premiums for the whole retroactive period come due, on the schedule and grace periods your election notice states.
• The price. The plan may charge up to 102 percent of the full cost of the coverage. That is the employer's share, your old share, and up to a 2 percent administration charge, in one bill, to you. The number shocks most people the first time because the employer's share was invisible while you worked there. In a disability extension, the charge can rise to 150 percent. Your election notice states your actual premium.
• How long it lasts. For a termination or a reduction in hours, continuation generally runs up to 18 months. The DOL lists 18, 29, or 36 month periods depending on the event and on extensions, and your election notice describes which apply to you and what can end coverage early.

The waiting question, answered carefully. Because election is retroactive, some people wait inside the 60-day window before deciding: if no medical need arises, they may choose another door instead, and if one does arise, they elect COBRA and pay the retroactive premiums. That sequence is a fact about how the retroactive rule works. It is also a risk you take with your eyes open:

• Miss the election deadline in your notice and the COBRA right ends. Retroactive does not mean forgiving.
• The Marketplace window below is its own 60 days from your loss of coverage. Time spent waiting on COBRA is time spent inside that window too. The two clocks do not pause for each other.
• If you elect COBRA and later drop it before it runs out, dropping it generally does not open a new Marketplace special enrollment window. Per the Department of Labor, ending COBRA early usually means waiting for the next Marketplace open enrollment or another qualifying event. Read that sentence twice before treating COBRA as a bridge you can step off at will.
• Retroactive premiums for several months, due at once, are real money. Run the figure in Worksheet 4 before the strategy, not after.

Door 2: The Marketplace

Losing job-based coverage opens a special enrollment period in the Health Insurance Marketplace at healthcare.gov (or your state's marketplace, which healthcare.gov will route you to). The federal rules:

• You have 60 days after losing job-based coverage to enroll.
• If you know the loss is coming, you may apply up to 60 days before it. Used well, this is the no-gap door: coverage can start the 1st of the month after your job-based coverage ends when you select a plan in time.
• The application asks for your estimated household income for the coverage year. Estimate honestly, using what you know today, and report changes through the Marketplace as the year develops. The application, not a guess from a friend, is where your premium tax credit is figured.

Read this before you price a plan. The enhanced premium subsidies from the pandemic period expired at the end of 2025. Do not price 2026 Marketplace coverage using a neighbor's 2024 premium or an old article. Run your own application for your actual numbers. Separately, the year-round special enrollment period that once existed for people under 150 percent of the federal poverty level was eliminated on August 25, 2025. It does not exist anymore. If your income is low, Door 4 below is the year-round door, not a Marketplace exception.

Door 3: A spouse's or partner's plan

If your spouse has a group health plan, losing your coverage can open a special enrollment opportunity in that plan. Federal guidance describes a 30-day special enrollment period to join another group health plan after losing coverage. Treat 30 days as a warning light, not a promise: this deadline is set by your spouse's plan, and the plan's summary plan description and benefits office control the exact request, the forms, and the date. Ask the benefits office in week one, by phone and in writing, these three things: Is loss of a spouse's coverage a special enrollment event under this plan? What is the last day to request enrollment? What documents prove the loss? Log the answers in Worksheet 6, and compare the plan's premium, deductible, and network in Worksheet 4 like any other door. A payroll-deducted premium for coverage your doctors accept can beat both other doors. You cannot know until it is on the worksheet.

Door 4: Medicaid and CHIP

Medicaid and the Children's Health Insurance Program provide free or low-cost coverage to eligible households, and you can apply any time of year. There is no enrollment window to miss. Eligibility is income based and set by your state, and states differ, including on whether they expanded Medicaid. Two practical points from healthcare.gov: apply even if you are not sure you qualify, because your state's program may count your household's circumstances in ways a guess cannot; and when you file a Marketplace application, it screens for Medicaid and CHIP automatically. If it looks like anyone in your household qualifies, the Marketplace securely sends your information to your state agency, and the state contacts you about enrollment. One application therefore tests two doors at once, which is why filing the Marketplace application early in your 60 days is sound even if COBRA is your expected answer.

Choosing, on paper

Fill Worksheet 4 with real figures for each door that is open to you: monthly premium, deductible, out-of-pocket maximum, whether your current doctors and prescriptions are in network, the date coverage starts, and the date the decision closes. Then decide. A premium you cannot sustain for six months is not cheaper than a premium you can, and a plan your doctor is outside of is not the same plan you had, whatever the card looks like.

PocketBack's COBRA vs. Marketplace Decision Workbook takes this one comparison, the job-loss coverage choice, and works it to the last line: premium math over the months you actually expect to need, retroactive premium totals if you wait to elect, and a deadline sheet for both clocks. It is linked from this guide's page at getpocketback.com. Everything you need to make the decision carefully is in this chapter and Worksheet 4. The workbook is for readers who want the arithmetic done in a structured form rather than on the back of the election notice.

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