How Stripe Smart Retries work
Stripe Smart Retries uses machine learning on the aggregate Stripe network to pick retry times that maximize success. Behind the scenes it looks at issuer behavior, decline codes, and time-of-day patterns. For most consumer subscriptions this beats a fixed schedule by a meaningful margin, with no configuration required.
When Smart Retries fall short
Smart Retries do not know your customer. They cannot tell that a $50,000 annual invoice for an enterprise account should not be silently retried four times and then churned. They cannot pause on a decline reason that requires a customer service action first. And they cannot escalate to a human. For SaaS with material contract value, you need logic that sits above the retry engine.
Configuring retry schedules in Stripe
- Enable or disable Smart Retries in Billing settings
- Set a custom retry schedule of up to four attempts over any window
- Choose what happens after the final attempt: mark uncollectible, cancel, or leave open
- Fire webhooks on every attempt so external tools can layer on their own logic
Retries are one lever, not the whole system
A retry that succeeds because the customer updated their card between attempts is a win driven by communication, not by retry timing. The best recovery numbers come from combining Stripe retries with a clean update-card page, well-timed emails, and a human on the largest cases.
How Chaser layers on top of Stripe retries
Chaser listens to Stripe webhooks, classifies every decline, and picks the right playbook per case: automated retries and messages for volume, and human escalation for high-value or ambiguous failures. Every case ends with a documented outcome so you can see exactly how much revenue your Stripe retries recovered and where they left money on the table.