Claude Code applied a schema change to a live database as part of a task, and the result is wrong. You want it reversed. What does the session offer you?

The principle — a restore point can only restore something it holds a copy of, and it holds copies of files.

Why the key is correct — Anthropic states the limit and, unusually, states the consequence in the same breath: actions that affect remote systems such as databases, APIs and deployments cannot be checkpointed, which is why Claude asks before running commands with external side effects. That approval prompt is the real control here, and it is placed where it is precisely because there is no undo behind it. Once the migration has run, recovery is a database problem — a down migration, a restore from backup, a manual correction — and the session has nothing to contribute.

Why the others are wrong — having happened during the session is not sufficient, because the mechanism is bounded by what it can snapshot rather than by when something occurred. The snapshot covers file contents on your disk and never extends into a service the session merely spoke to. And rewinding a turn reverses the tracked file edits in it; an action whose effect lives elsewhere leaves nothing local to reverse, so the turn comes back looking clean while the database does not.

It is worth noticing that the documentation gives the reason for the prompt rather than only the rule: the approval exists because the reversal does not.

Remember this — the approval prompt before a command with external side effects is the last point at which the decision is cheap. Treat it as the undo, because nothing downstream of it is one.

Sources — Anthropic's How Claude Code works and the checkpointing page.