When Blog: COBRA, Medicare & Workforce Transitions

Dark plum blog header. Headline reads "Not on the report. Still on the plan," above an eyebrow with the When tulip that says "COBRA · the hidden cost." On the right, a "High-Cost Claimant Report" panel lists dim data columns — Claimant, Diagnosis, Paid — beside a highlighted, dashed-outlined "STATUS?" column, with a glowing amber dollar-sign coin sitting in that column to represent the hidden COBRA cost the report leaves out.

Insight

Jul 28, 2026

COBRA Doesn't Show Up on the Plan Report. That's Why It Keeps Costing You.

Tom Cox

Pricing · two models — PEPM or utilization? We offer both. One flat number, or pay as it's used." On a dark plum background, two cards: one showing a flat line labeled "PEPM / Predictable," the other a rising-and-falling usage line labeled "Utilization / Aligned."

PEPM Is Predictable. Utilization Is Aligned. Why We Offer Both.

"COBRA · Qualifying events — Seven events. You plan for one. Six more you never see coming." A row of seven event tiles on a dark plum background, with a spotlight illuminating one (the layoff) while the other six sit in shadow.

COBRA Qualifying Events: The Full List Beyond Layoffs

Advisory Firm vs. Licensed Agency: Who Can Actually Enroll?

It's Not If, It's When: Build Your Off-Boarding Plan Before You Need It

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Insight

Jun 18, 2026

The Best Cost-Containment Solution Is the One You Can Implement the Fastest

Brook West

Insight

Jun 18, 2026

The Best Cost-Containment Solution Is the One You Can Implement the Fastest

Brook West

Insight

Jun 18, 2026

The Best Cost-Containment Solution Is the One You Can Implement the Fastest

Brook West

Insight

Jun 17, 2026

Your Aging Workforce Is a Benefits Cliff. Here's the Data.

Carly Keller

Insight

Jun 17, 2026

Your Aging Workforce Is a Benefits Cliff. Here's the Data.

Carly Keller

Insight

Jun 17, 2026

Your Aging Workforce Is a Benefits Cliff. Here's the Data.

Carly Keller

Stories

Jun 9, 2026

Why Our Agents Don't Work on Commission

Dan Wertheimer

Stories

Jun 9, 2026

Why Our Agents Don't Work on Commission

Dan Wertheimer

Stories

Jun 9, 2026

Why Our Agents Don't Work on Commission

Dan Wertheimer

Insight

Jun 1, 2026

What HR Can and Can’t Say About Medicare (Without a License)

Dan Wertheimer

Insight

Jun 1, 2026

What HR Can and Can’t Say About Medicare (Without a License)

Dan Wertheimer

Insight

Jun 1, 2026

What HR Can and Can’t Say About Medicare (Without a License)

Dan Wertheimer

Insight

May 21, 2026

The Captive Blind Spot at the Exit Door

Tom Cox

Insight

May 21, 2026

The Captive Blind Spot at the Exit Door

Tom Cox

Insight

May 21, 2026

The Captive Blind Spot at the Exit Door

Tom Cox

Insight

May 19, 2026

Benefits Consultants, the 2027 Renewal Math Is Already Brutal. Here Are the Two Levers That Actually Move the Number.

Tom Cox

Insight

May 19, 2026

Benefits Consultants, the 2027 Renewal Math Is Already Brutal. Here Are the Two Levers That Actually Move the Number.

Tom Cox

Insight

May 19, 2026

Benefits Consultants, the 2027 Renewal Math Is Already Brutal. Here Are the Two Levers That Actually Move the Number.

Tom Cox

Insight

Apr 14, 2026

"Our Plan Is Too Rich. They'll Always Choose COBRA."

Carly Keller

Insight

Apr 14, 2026

"Our Plan Is Too Rich. They'll Always Choose COBRA."

Carly Keller

Insight

Apr 14, 2026

"Our Plan Is Too Rich. They'll Always Choose COBRA."

Carly Keller

News

Apr 8, 2026

P&A Group Partners with When to Deliver Healthcare Transition Support for Employer Clients

Tom Cox

News

Apr 8, 2026

P&A Group Partners with When to Deliver Healthcare Transition Support for Employer Clients

Tom Cox

News

Apr 8, 2026

P&A Group Partners with When to Deliver Healthcare Transition Support for Employer Clients

Tom Cox