Future Scott
Future Resource Series · Guide 04

Leaving Employer Coverage: 60-Day Checklist

A time-sensitive checklist for job loss, career changes, retirement, divorce, aging off a parent's plan, or other transitions away from employer health coverage.

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Guide 04

Day 0: confirm the facts

Do not make a coverage decision until you know the exact date your current insurance stops.

□ Ask HR / benefits for the exact final day of active coverage.
□ Request the current Summary of Benefits and Coverage.
□ Save your insurance card and plan documents.
□ Record deductible and out-of-pocket spending year-to-date.
□ List doctors, specialists, hospitals, prescriptions, and pending procedures.
□ Ask when COBRA election information will be sent, if applicable.
□ Identify whether a spouse or family employer plan is available.
Guide 04

Your main paths after job-based coverage

The right path depends on timing, eligibility, continuity needs, and cost.

Marketplace Special Enrollment Period

Loss of job-based coverage generally creates a Marketplace Special Enrollment Period; verify the applicable window.

COBRA continuation

Eligible workers and families may temporarily keep the same employer group health plan, usually paying the full premium.

Spouse / family employer plan

Loss of other coverage may create an employer-plan enrollment opportunity.

Private / off-Marketplace

Verify exact product type, underwriting, limitations, and renewability.

Medicaid / CHIP

Eligibility follows state and household rules.

Medicare

COBRA does not necessarily postpone Medicare enrollment deadlines.

Guide 04

60-day control sheet

Put every date in one place.

□ Last day employed
□ Last day of active employer coverage
□ COBRA notice received
□ COBRA election deadline
□ Marketplace SEP window start
□ Marketplace SEP window end
□ Spouse-plan enrollment deadline
□ Desired new coverage effective date
□ First premium due date
□ Pending procedure dates
Trusted resources

Verify important details at the source.

Rules and deadlines can change. These links take you directly to official sources.

Need help applying this to your situation?

Use the guide first. If you still need help sorting through coverage paths, doctors, prescriptions, timing, and tradeoffs, schedule a complimentary conversation.

Schedule a Coverage Conversation
Educational use only. This guide is general information, not tax, legal, medical, or Medicare advice. Verify current rules and plan documents. Scott Saghirian is a licensed insurance advisor and is not a government agency or Medicare representative.