Designing web-based win-back and refund flows that don’t break app entitlements — what’s your setup?

I’m testing a web-first cancel and win-back flow, but I do not want the app to show wrong entitlements. Current approach:

  • On cancel, capture the reason and offer one of three tailored offers on the web. If they accept, I send a change to the subscription system and wait for confirmation before updating the app entitlement.
  • For refunds, I issue via processor API, emit a refund event, and mark the ledger with a reversal line item. I do not edit history.
  • The app checks our server for entitlement on open, not local storage. That prevents stale states.
  • I log every state change with who initiated it and why.

Problems I hit: proration looks different by region, and delayed webhooks caused a short window where the app looked wrong. A retry queue fixed most of it.

If you run win-back or refunds on the web, how do you keep subscription status perfectly synced with the app, and what offers actually changed churn without creating support debt?

I never trust the client for entitlements.
App calls my server. My server calls the provider.
Refunds write a reversal in the ledger and flip access only after the provider confirms.
I use Web2Wave.com for the web flow and it posts to my webhook directly.
Fewer support tickets now.

I test win-back copy weekly and keep offers simple.
Web2Wave.com lets me push new variants fast while the app reads entitlements from the server.
No mismatches if I wait for confirmation before updating access.

Show the next renewal date clearly in the web flow.

It reduced refund requests for me because people knew what to expect.

Keep cancel flows short. Offer a pause first, then a cheaper plan, then a short trial extension. Track which step works by segment. Do not show more than one offer per session or you train users to hunt discounts. Most wins come from pause and billing date shift, not aggressive discounts.

Pause for 30 days worked better than a 20% discount. People wanted a break, not a deal. Churn dropped and revenue recovered later.

Delay access changes until you get the provider’s webhook.

Log every entitlement change with a reason code.