Plan the Rollback

The riskiest moment of any change is "we'll figure it out if it breaks." That's not a plan. This skill enforces writing the rollback before doing the thing.

When to use

• About to apply a DB migration (especially destructive: drop, alter type, rename, NOT NULL).
• Cutting over to a new vendor (auth, payments, email, hosting).
• Changing a config that affects all users (feature flag default, rate limit, cache TTL).
• Renaming an API field consumed by clients.
• Deploying a new service that takes traffic for the first time.
• Any change where "if this breaks at 2am, what do we do?" doesn't have a one-sentence answer.

When NOT to use

• Pure code change with green tests, no schema or external service impact.
• Reverting a recent change (rollback is the plan).

The four-question rollback plan