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The existing tests covered updateCrewTierWithRetry and UpdateCrewTierOnHold. UpdateCrewTierOnAllHolds -- the function the Stripe webhook actually calls, and whose error decides whether a paid upgrade is retried or dropped -- had none. Three cases: the joined error names every failing hold and not the one that succeeded; a hold that accepts and never answers does not starve the holds after it (mutation-verified by making the fan-out serial, which leaves the healthy hold contacted zero times); and a context deadline aborts the retry loop rather than running to tierUpdateMaxAttempts. That last one records a real mismatch rather than an intent. Three attempts at a 5s client timeout need ~15s, and the webhook allows the whole fan-out 10s, so under a hang the budget funds two attempts and never three -- confirmed against a blackholed hold on the dev stack, which failed at exactly 10.0s with a bare context error rather than the "after N attempts" wrapper. If either constant or the deadline moves, that test is where the arithmetic gets re-checked. Also covers the other half in pkg/billing: a fan-out failure has to reach Stripe as a 5xx and leave stripe_processed_events empty. A hold that is briefly down otherwise costs the customer their tier permanently -- the same shape of loss as the customer-lookup hole, one layer further out. Co-Authored-By: Claude Opus 5 (1M context) <noreply@anthropic.com> Claude-Session: https://claude.ai/code/session_01VwxF2N3HuZ8xSkx6nkirgB