When a payment fails, the next step depends on the payment method, the failure reason, and whether the payment was one-time, recurring, or automatic. Aiwyn does not apply one universal automatic retry schedule to every failed payment.
Where to monitor failed payments
Use the Payment Failures report to monitor unsuccessful payments and their recovery outcomes. The report shows failure reasons, recovered failures, recovery time, and clients with repeated failures.
The report opens to the previous rolling 30 days by default. Change the Failed on Date filter when you need to evaluate a different period.
What happens after a payment fails
Automatic retry is not the default
Most failed payments are not retried automatically on a fixed schedule. Stripe smart retries are not currently built into Aiwyn's connected-account payment workflows, and there is no firm-facing setting for configuring a universal retry count or cadence.
Recurring ACH payments are the main exception, but even there the failure reason determines what can happen next:
- Insufficient funds or another re-debitable return: Aiwyn Support contacts the client and firm and waits for explicit approval before issuing a one-time re-debit. After approval, the payment is re-debited within the next few business days.
- Debit block or authorization problem: The client must resolve the issue with their bank before another debit can be attempted. A re-debit still requires approval.
- Closed, invalid, or unlocatable account: The same bank details cannot be retried. The recurring plan is canceled and the client must provide a different payment method.
If neither the client nor the firm responds to recurring-payment outreach within two business days, Support may cancel the recurring plan and close the case.
Do not wait for an assumed retry.
Check the failure reason and payment context. A retry is appropriate only when the return reason permits it and the required approval or corrective action has been completed.
Card failures
A card decline that happens while the client is paying appears immediately in the Client Portal with a message and an option to try again or use another method. By design, Aiwyn does not send a failure email for these live card declines.
A failed scheduled or automatic card payment follows the asynchronous notification path instead: the client and firm receive a failure email and may need to update the payment method before the next payment.
Client and firm notifications
For bank-debit failures and scheduled or automatic payments, Aiwyn sends failure emails to the client and firm. The firm recipient is the contact configured to receive billing or recurring-payment-plan notifications. Some recurring-plan failures also enter a Support workflow in which Support contacts the client and copies the firm.
Current failure emails identify the affected payment but may not include the specific reason, a resolution, or a retry action. Clients can see an immediate reason for a live card decline, while payment history in the Client and Firm Portals may show only a Failed status.
How the report defines recovery
The report measures the outcome at the invoice level. It does not require the successful payment to be an automatic retry of the original transaction.
- Recovered Payment Failures: The percentage of payment failures for which the originating invoice later had a successful payment. A later payment for the same invoice can qualify, including a payment completed after firm or client follow-up.
- Median Days to Recover: The median number of days between the first failed payment for an invoice and the first successful payment for that invoice.
Because the report infers recovery from a later successful payment, it does not identify which phone call, email, payment-method change, or other follow-up action caused the recovery.
How repeated failures are identified
Multiple Payment Failures is the percentage of clients with more than one failed payment in the selected report period, divided by the clients with at least one failed payment in that period. The default period is the previous rolling 30 days, but the result changes with the report filters.
This is a reporting threshold, not a separate permanent risk flag. Use the Payment Failure Insights table to review the affected clients, failure reasons, payment IDs, and invoice context.
What firm staff should do
- Review the failure reason and determine whether the same payment method can be used again.
- For a live card decline, have the client retry or use a different method based on the message shown.
- For a recurring bank-debit failure, wait for the required approval before requesting a re-debit.
- For a non-retriable bank return, update or cancel the plan and ask the client for a new payment method.
- Use the report's recovery metrics to measure whether the invoice was eventually paid, not whether a specific automated retry succeeded.
Related articles
- What is the payment failures report?
- Review payment recovery metrics
- Troubleshoot a failed client payment