COBRA Deadlines

COBRA lets you continue your old employer's health plan after job loss or hours reduction — at full price plus 2%. It's brutally expensive, but the deadlines are what actually trap people: miss a 60-day window and the option evaporates permanently. Here's every clock that matters.

The deadlines

• Election: 60 days from the later of your coverage loss or the COBRA notice date. Miss it and COBRA is gone forever.
• First payment: 45 days after electing. Coverage is retroactive to the loss date once you pay.
• Ongoing payments: 30-day grace period each month. Miss the grace period and coverage terminates — no reinstatement.
• Duration: 18 months standard (29 with disability extension, 36 for certain second events like divorce).
• Marketplace SEP: 60 days from coverage loss — runs concurrently; you can choose Marketplace instead of COBRA.

The strategic play most people miss

Because COBRA is retroactive, a healthy person can wait out most of the 60-day election period uninsured, then elect only if a medical event occurs — effectively free catastrophic coverage for the gap. It's a gamble (a crisis on day 61 with no election is catastrophic), but it's the rational use of COBRA's structure. Meanwhile, compare Marketplace plans immediately — for most people, the Marketplace wins on price from day one.

When COBRA actually wins

• Mid-deductible: you've already spent thousands toward the old plan's deductible this year — switching resets it.
• Ongoing treatment: mid-chemotherapy, mid-pregnancy — continuity with the same network has real value.
• Short gaps: new employer's benefits start in 45 days — COBRA bridges cleanly.

Common COBRA mistakes

• Electing immediately out of panic — compare Marketplace options first; COBRA is rarely the value winner.
• Missing the 60-day election window — it evaporates permanently; calendar it the day you get the notice.
• Missing a monthly payment — the 30-day grace period is unforgiving; set autopay.
• Not using the retroactive strategy — healthy people can often wait and elect only if needed.

Pro tip: the day your COBRA notice arrives, do three things: calendar the election deadline, get Marketplace quotes, and compare total costs — in that order.

The bottom line

COBRA's power is its retroactivity; its danger is its deadlines. Calendar every 60-day clock the day the notice arrives, compare Marketplace options immediately, and use COBRA strategically — not reflexively.

Key takeaway

COBRA is retroactive, expensive, and governed by unforgiving 60-day clocks. Calendar the election deadline immediately, compare Marketplace alternatives the same day, and use COBRA as a strategic bridge — not a panicked default.

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