One-Time vs. Auto-Reimbursement: Why Your Client's Employees Might Need Both

For agents: Auto-Reimbursement is not retroactive. Employees often need a one-time reimbursement for months before AR was approved — that doesn’t mean AR is “broken.”

Setup-timing gap (most common)

Example: an employee paid a July premium, but their Auto-Reimbursement setup wasn’t approved until early August. July won’t automatically be included. They should submit a One-Time Reimbursement for July (with proof of coverage / premium documentation), while AR covers August forward once Active.

Binder / first-premium months

Employees pay the carrier binder/first premium themselves. They can then use StretchDollar reimbursements (often a one-time request first) to get employer ICHRA dollars back into their bank account, and enroll in Auto-Reimbursement for ongoing months. StretchDollar never pays the carrier. Point employees to How employees access their benefit dollars to help with their initial (binder) payment for the employee-facing steps.

Deactivation note

If an employee is terminated/deactivated, Auto-Reimbursement is typically canceled. During the grace period they may still be able to submit one-time reimbursements — see What Happens to Billing and Reimbursements When an Employee Is Terminated?

What to tell a client

Both one-time and auto paths need Admin approval. After approval, StretchDollar initiates employer→employee ACH. Timing depends on approval + banking settlement (auto monthly runs typically around the 25th for the following coverage month). If a payment doesn’t land, don’t assume the carrier was unpaid by StretchDollar — see the bank-transfer bounce article.