Why are my employee insurance enrollments always broken?
- Claire Baker
- Oct 19
- 2 min read
Are your insurance deductions messed up again?
Here. Let me help.
The many layers of humans and technology that go into insurance deductions can make it hard to track down where the problem is. And because of the old school systems insurance companies still use, it can be like traveling back in time.

Layer 1: Payroll
Insurance rates aren't magically uploaded into your payroll platform. Somebody has to put them there. If they entered them wrong, your deductions will be wrong.
💡 If the books don't balance, check your payroll settings first.
Layer 2: Enrollment
Something has to collect deduction data AND enrollment info any time something changes. It could be your payroll platform itself, third-party software, or a PDF or paper form. If something gets stuck at this step, you'll either have deductions but no insurance, or insurance but no deductions.
💡 If payroll and insurance have different records, check with whoever's supposed to communicate between the two.
Layer 3: Submission
Enrollment isn't always automatically pushed to the insurance company. Even with software platforms, there's often a human sending a CSV or PDF file to another human in the background. Sometimes that human forgets.
💡 If the insurance company doesn't have a record of the enrollment/change, talk to the person who was meant to send it. Hint: It's the person responsible for Layer 2.
Layer 4: Processing
Insurance companies are full of unimaginative humans checking forms. Sometimes they open the email and forget about it, or get hung up on a technicality. No matter what couch cushion the application slipped between, everything stops.
💡 If the enrollment/change was submitted but never processed, follow up with the insurance company.
Layer 5: COBRA
Often COBRA goes through completely different channels. Which means that any of the steps above could happen with a different cast of characters.
💡 If it's COBRA, go through the layers above in reverse.
Let us be your insurance gumshoe. If you can't figure out why it's broken, we can help.



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