Free resource · Reviewed for 2027
Between Jobs: Your 30/60-Day Health Coverage Checklist
Four facts to get before you leave, your options in the order to check them, and the deadlines that matter.
1. Day 0: get these before your last day
☐ The exact date your health coverage ends. Ask HR: "Last day of work, or end of the month?" Every deadline is counted from this date. ☐ The date your COBRA election notice will be mailed, and the monthly COBRA premium for your household ☐ Your current plan's summary of benefits, including the deductible and out-of-pocket maximum ☐ What you've already paid toward this year's deductible
2. Your options, in the order to check them
① Private health plan. You buy it directly and can often apply any time of year. Start dates vary by plan, but coverage usually begins the first of the following month, so apply before your work coverage ends to keep any gap short. It may ask health questions and may exclude some conditions, so read the exclusions along with the price.
② COBRA. It keeps your exact plan, generally for up to 18 months after a job loss, at employers with 20 or more employees. You pay the full premium plus up to 2%. If you elect within the window, coverage is retroactive.
③ Your spouse's employer plan. You can usually join within at least 30 days of losing coverage. Ask about the cost to add you and any spousal surcharge.
④ The Marketplace (fallback). Losing coverage opens a 60-day Special Enrollment Period. Plans accept pre-existing conditions, and a tax credit is based on your whole-year income estimate, including severance.
3. Your deadline calendar
| Deadline | Rule | My date |
|---|---|---|
| Coverage ends | from HR | ____ |
| Spouse's plan, last day to join | at least 30 days after coverage ends | ____ |
| Marketplace SEP closes | 60 days after coverage ends | ____ |
| COBRA election closes | at least 60 days after the later of coverage end or notice | ____ |
4. COBRA: keep it or skip it?
COBRA often makes sense if:
- You've met most of this year's deductible
- You're mid-treatment and can't change doctors
- A new employer plan starts within a few months
It's usually worth comparing first if:
- You're healthy and it's early in the year
- The premium is coming out of savings
⚠ If you elect COBRA and later drop it on purpose, that usually won't open a Marketplace Special Enrollment Period. Decide while your 60-day window is still open.
5. Before you enroll in anything
☐ Look up every doctor and pharmacy by name in the plan's network ☐ Check each prescription on the plan's drug list ☐ Add premium + deductible to see your worst-case year, not just the monthly cost ☐ Set the start date so there's no gap after your work plan ends
Take the free Find My Plan quiz, or talk with a licensed agent by phone or text. Jeff Weisblatt, 817-980-8804 (licensed in 28 states) · Amy Herdine, 817-470-2229 (licensed in Texas)
Sources: U.S. Dept. of Labor, An Employee's Guide to Health Benefits Under COBRA (18 months, 20+ employees, 60-day election, retroactive, 102%). U.S. Dept. of Labor, HIPAA special enrollment rights (30 days). HealthCare.gov, Special Enrollment Period and COBRA coverage (60 days; voluntary COBRA drop). HealthCare.gov, Pre-existing conditions. General information, not legal, tax or medical advice.
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