How It Works

When a subscription renewal fails, Retain automatically steps in — no seller action required. It detects the failure through its connection to Paddle Billing and Paddle Classic and begins recovery immediately.

Recovery works through three tools:

• Tactical Retries (Smart Retries): Retain retries the failed payment at algorithmically determined optimal times, based on decline reason, card type, buyer location, and 15+ other signals. Retries are invisible to the buyer unless one succeeds.
• Dunning Emails: Up to 4 automated recovery emails prompting the buyer to update their payment details, timed alongside retry attempts. If a retry succeeds before an email is due, that email is suppressed.
• In-App Notifications: Buyers with a past_due subscription see a persistent in-app prompt to update their payment method when they log in, regardless of whether they've opened recovery emails.

The Current Retry Cadence

As of April 2026, Retain supports up to 7 retries for both Paddle Billing and Paddle Classic. This payment retry behaviour is automatically enabled for Paddle Billing accounts. §The default cadence:

1. ~2 hours after the initial failure — 1st retry (+ 1st recovery email if retry fails)
2. ~3 days later — 2nd retry (+ 2nd recovery email if retry fails)
3. ~2 days later — 3rd retry (+ 3rd recovery email if retry fails)
4. ~2 days later — 4th retry (+ 4th and final recovery email if retry fails)
5. ~Day 10 — 5th retry (no email)
6. ~Day 15 — 6th retry (no email)
7. ~Day 20 — 7th retry (no email)

Retry timing is dynamic — Retain's algorithm adjusts based on failure reason, location, and other factors. Retries 1–4 typically complete within 10–12 days; retries 5–7 extend to around day 20. The 7-retry cadence is feature-flag controlled and may not apply to all configurations.

Retain's upgraded scheduler now delivers up to 7 retries natively — for both Paddle Billing and Paddle Classic. Classic sellers no longer rely on the platform's native cadence; Retain handles all retries uniformly, with an expected ~20% lift in recovery performance. Emails accompany only retries 1–4. Retries 5–7 run silently but can still recover a payment. 

If by the end of the dunning period (Paddle Billing’s default is 30 days) and the customer is still not recovered, the customer then becomes involuntary churned. 30 day window can be adjusted by Seller.

Key Behaviors & Edge Cases

• Not all failures are retried. Retain only retries where recovery is likely — e.g. insufficient funds or a temporary bank block. Fraud-flagged failures are excluded.
• Retry timing is not customisable. The schedule is managed by Retain's algorithm. The dunning window length, however, is configurable (default: 30 days).
• End-of-window behavior is configurable. Sellers set whether a subscription should cancel, pause, or go past due at window end. The default is cancellation after 30 days.
• First-time payments are not retried. Retain only handles failed renewal payments on existing subscriptions — initial checkout failures are not picked up.
• Banks have limits. Retain caps retries at a sensible count (generally no more than 10 total), since excessive retries can be flagged negatively and hurt future acceptance rates.

What to Expect as a Seller

Once Retain is configured, recovery runs automatically:

1. A subscription renewal fails. Retain detects this automatically — no webhook or API call needed from the seller.
2. Within roughly 2 hours, the first retry is attempted. If it succeeds, no email is sent and the subscription continues normally.
3. If the retry fails, the buyer receives the first recovery email prompting them to update their payment details.
4. This continues for up to 4 email/retry cycles over ~10–12 days, followed by up to 3 silent retries extending to around day 20.
5. Throughout the dunning window, buyers who log into the seller's app see in-app notifications prompting payment method updates.
6. At the end of the dunning window (default: 30 days), the subscription is cancelled, paused, or left past due — depending on what the seller has configured.