How auto-reimbursement timing works: a guide for agents

This article explains how auto-reimbursement (AR) timing works on StretchDollar, so you can set expectations with your clients and their employees and answer "when will I get paid?" questions.

The short version

  • First month: paid when the employer's admin approves the employee's AR setup, as long as the admin approves before the plan start month ends. The employee doesn't wait for the monthly run.
  • Every month after: paid by the run on the 25th, which collects next month's reimbursement from the employer. The September 25 run pays October.
  • Approved after the 25th: next month is paid right away as a catch-up, so the employee doesn't miss a month.
  • Timing: payments made at approval usually reach the employee 3–5 business days after processing. Monthly payments arrive around the 1st.

How the system works, step by step

  1. The employee sets up auto-reimbursement after buying their plan. They enter their premium, upload proof of coverage, and choose when coverage for the plan begins (the plan start month).
  2. The employer's admin approves it in the Company Portal. The approval window shows exactly what will be debited and when.
  3. At approval, StretchDollar can pay up to two months immediately from the employer's connected bank account:
    • the first month of the plan, if the plan start month is the current month or later, and
    • next month, if this month's 25th run has already happened.
  4. On the 25th of every month after that, the scheduled run collects next month's reimbursement, and it arrives around the 1st.

Timeline examples

Scenario Paid at approval Next payment
October plan, admin approves Oct 10 October November, from the Oct 25 run (around Nov 1)
October plan, admin approves Oct 27 October and November (catch-up) December, from the Nov 25 run (around Dec 1)
November plan, admin approves Oct 28 November December, from the Nov 25 run (around Dec 1)
August plan, admin approves Sep 3 Nothing for August The employee submits a One-Time Reimbursement for August

When a month isn't paid automatically

  • The admin approved after the plan start month ended. Months before approval aren't paid retroactively, so the employee submits a One-Time Reimbursement.
  • The month was already reimbursed, for example through a One-Time Reimbursement. There's no double payment.
  • The plan starts before the employee's ICHRA benefit begins. Months before the benefit starts aren't paid.
  • The employee's allowance for that month is already used.
  • The employer's bank account doesn't have enough funds when the payment is pulled. The transfer fails, and support follows up with the employer.

What to tell your clients

  • Admins: approve new AR setups promptly, ideally before the employee's plan start month ends and before the 25th. Keep enough funds in the connected bank account, because first-month and catch-up payments are pulled at approval, not on the 25th.
  • Employees: set up AR as soon as you've bought your plan, choose the correct plan start month, and nudge your admin to approve. If any month is ever missing, submit a One-Time Reimbursement.
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