Why Your Auto-Reimbursement Timing Matters: The 25th Rule

When Will I Receive My Auto-Reimbursement?

Auto-reimbursements run on a steady monthly schedule. Your first month works a little differently, so you aren't left waiting for money you've already spent on your plan.

Your first month: paid when your admin approves

When you set up auto-reimbursement, we'll ask for your plan start month, which is the first month your health coverage begins.

Once your admin approves your setup, a reimbursement for that first month is processed automatically. You don't have to wait for the regular monthly cycle. This helps if you've already paid your first premium (sometimes called a binder payment) to activate your plan.

When your first month won't be paid automatically

Your setup is approved after your plan start month has passed. For example, your plan starts in August, but your admin approves on September 3. Submit a One-Time Reimbursement for August and any other months you missed.
You already received a One-Time Reimbursement for that month. Since that month is already covered, a second payment won't be created.
Your plan starts before your employer's benefits begin. For example, your plan starts in August, but your employer's ICHRA benefits start in September. August won't be paid automatically. You can still submit a One-Time Reimbursement for August, and your employer can choose whether to approve it.

Why your first payment isn't instant

Bank transfers take time to move between accounts, and we can't speed that up. Your first-month reimbursement usually arrives in your bank account 3–5 business days after the reimbursement is processed. Weekends and bank holidays don't count as business days, so they can add a little extra time.

Example: Your plan starts October 1. You submit your auto-reimbursement setup on September 30, and your admin approves it the same day. Your October reimbursement is processed after approval, but the money won't be in your account on October 1. Expect it 3–5 business days after it's processed, depending on weekends and your bank.

Your setup must be approved before your first-month reimbursement can be processed. If your admin approves later, your payment will arrive later too.

Every month after that: the monthly cycle

On the 25th of each month, StretchDollar pulls funds from your employer's connected bank account.
Those funds are sent to employee bank accounts around the 1st of the following month.

What this means for you

If you're an employee setting up auto-reimbursement:

Your first month is reimbursed once your admin approves, as long as approval happens before your plan start month ends. The money usually arrives 3–5 business days after the reimbursement is processed.
After that, if your setup is approved before the 25th, your next payment arrives around the 1st of the following month.
If approval happens after the 25th, your next regular payment arrives around the 1st of the month after that.

Example: Your plan starts in November. You finish setup on October 27, and your admin approves on October 28.

→ Your November reimbursement is processed after approval and usually arrives 3–5 business days after it's processed.

→ The October 25 cycle has already passed, so your next regular payment arrives around December 1.

If you're missing a reimbursement for any month, you can submit a One-Time Reimbursement to your admin.

If you're an admin:

When you approve an employee's auto-reimbursement, their first month of coverage is reimbursed automatically from your connected bank account, unless one of the exceptions above applies.
The sooner you approve, the sooner your employee gets paid. Their first-month reimbursement usually arrives 3–5 business days after it's processed.
Approving before or during the employee's plan start month means they won't need to submit a One-Time Reimbursement for that month.
Approving before the 25th means the employee is included in the current monthly cycle. Approvals after the 25th are queued for the next cycle.