Navigating Subscription Overhauls and Payments

Navigating Subscription Overhauls and Payments

June 19, 2026 · 28 min · Episode 355

About this episode

The hosts discuss practical Rails work related to subscription and billing migrations at Podia, including challenges with Stripe and Action Mailer.

Chris, Andrew, and David catch up after a missed week of recording and quickly dive into the kind of deeply practical Rails work that only comes from real production pain. Andrew shares the massive subscription and billing migration happening at Podia, including Stripe edge cases, legacy plan preservation, and stress-test tooling built from live scenarios. Chris then goes deep on a Hatchbox email cancellation flow that turns into a Rails internals rabbit hole around Action Mailer callbacks, m...

People in this episode

Hosts: Chris Oliver, Andrew Mason, David Hill

Topics covered

Keywords

Mentioned in this episode

Organizations: Podia, Stripe

Books & works: Hatchbox

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