How Auto-Reimbursement Approvals Work
Admin Guide
As an admin, you're the last step before your employees' monthly health benefit reimbursements go out. When an employee sets up auto-reimbursement, it lands in your queue for a quick review — approve it once, and payments run automatically every month after that.
Where to find pending approvals
- Log in to your Company Portal.
- Click Auto Reimbursements in the left-side menu.
- You'll land on the Pending tab by default — this is where new employee submissions show up.
The Auto-Reimbursement page: Pending tab, submission table, and Approve/Reject buttons.
What you'll see in the table
Each row is one employee's submission. Here's what the columns mean:
| Column | What it tells you |
| Insurance Type | Health, Vision, or Dental |
| Year | Plan year the reimbursement applies to |
| Employee | Who submitted it |
| Submitted | The date they submitted |
| Status | Pending, Approved, or Rejected |
| Amount | The monthly premium amount they entered |
| Start / End | Coverage period dates |
| Proof of Coverage | Click the icon to view the document they uploaded |
| Notes | Why they're submitting (e.g., "I changed my plan mid-year") |
A pending submission for an employee, showing amount, dates, proof of coverage, and notes.
How to review a submission
- Click the Proof of Coverage icon to open the document the employee uploaded.
- Check that it matches the amount and coverage dates they entered.
- Compare the amount to their monthly allowance — StretchDollar will only ever reimburse the lesser of the premium amount or their allowance, so a mismatch here isn't necessarily a problem.
- Click Approve or Reject.
That's it — once approved, the setup runs automatically every month going forward. You won't need to re-approve it unless the employee changes plans or resubmits.
What the employee's submission looked like
For reference, here's the form your employee filled out before their request landed in your queue. It's helpful context if a submission looks unfamiliar or you want to understand what information they were asked to provide.
The employee-facing Set Up Auto-Reimbursement form.
Payment timing
Approved auto-reimbursements are processed automatically each month:
- Funds are withdrawn from your business bank account on the 25th
- Deposited into the employee's bank account on the 1st of the following month
What counts as valid proof of coverage
Employees can submit any of the following:
- A bill or invoice from their insurance provider
- A screenshot of their enrollment confirmation page
- A screenshot from their health insurance online portal
- An email confirmation of enrollment
- Their healthcare.gov confirmation page
Note: Approval is ultimately your call — if a document looks unclear or you're unsure it's valid, you can reject it and ask the employee to resubmit with clearer documentation.
Troubleshooting
- A submission won't approve — make sure proof of coverage was actually uploaded; the icon will be missing if it wasn't.
- The employee says their reimbursement didn't run — check that the submission is actually in Approved, not still Pending.