Hacking a health plan: Finding flexibility in a QLE
- Claire Baker
- May 18
- 3 min read
“I don’t know if you can help, but my last company really screwed me.”
This guy had just joined our team a few months earlier. We were thrilled to snatch up someone with his qualifications after he was laid off. He was relieved, too—his son had just been diagnosed with diabetes so employer-sponsored insurance was his priority.
“I turned down our insurance because I didn’t want to change Milo's doctors while they were still figuring out his insulin,” he said. “I figured I’d switch when the COBRA subsidy ended.”
No one told him the subsidy ended after four months, but the plan continued for six more.

Now his old HR team was saying he had to pay the full COBRA premium until their open enrollment.
Unless he had a qualifying event.
Which he had.
Two months ago.
Now the enrollment window had closed.
“If they'd just TOLD me, I would have made a different decision. It’s almost $3,000 a month. I can’t pay that and the mortgage.” His fists let go and he looked dejected. “There’s probably nothing you can do. I’m just venting.”
I wanted to punch something, too. “If we were willing to pay for your plan two months ago, I don’t see why we wouldn’t pay now,” I said. “Let me make some calls.”
I picked up the phone. I sat through the usual Qualifying Event 101 lecture.
“Yes, I know we don’t have to offer coverage. But what if we want to? Because it’s the right thing to do?”
I paused to let it land.
“It’s, like, his entire paycheck," I went on. "Does that seem right to you?”
You’re not gonna make him choose between his kid’s meds and the roof over his head, are you? hung in the air, unspoken.
Misinformation, misrepresentation, misconduct, or inaction of someone working in an official capacity to help you enroll (like an insurance company, navigator, certified application counselor, or agent or broker) kept you from enrolling in a plan or the right plan for you.
“Let me check with my boss. Please hold.”
I went through the same script with the boss. "Let me see what my boss says," the boss said. "Please hold."
Eventually, I reached someone who knew. "I'll send you the appeal form," she said. "You'll need to write a letter on company letterhead and sign with blue ink. But if the company makes the request, they'll approve it."
I bit back a sarcastic comment about letterhead. “Thank you. I’ll get it to you within the hour.”
And they did approve it. They even escalated it so it went live before the first of the month.
People treat insurance rules like they’re carved in stone. They’re not.
If someone was misled, misinformed, or caught in a gray area—and the company’s willing to go to bat for them—there’s usually a path.
You might need to create a letterhead template. Or find a printer. Or figure out how to fax. But if you can figure out how to communicate like it's 1996, you can probably figure out how to backdate a plan by a few months.
If your conscience is whispering “this can’t be right…” maybe it's time to push back. Sometimes it's just a question of figuring out where to push.
By the way, I think I'm required to tell you here that I'm a licensed insurance broker.
NPN: 21374929
That's not all I do, but it's something I can do.
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