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Let's say I call out to an external service, get some results, use them in a transaction which then crashes. As a result, the transaction is rolled back. The same effect can be achieved with save points and an explicit rollback.

Since Salesforce had the result of a synchronous callout, the callout did go to an external service. Also, since Salesforce does not control external services, any work done on external systems is not rolled back.

Am I correct in my understanding?

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Yes. Your understanding is correct. You need to send external system a request to rollback. Otherwise it will be out of sync.

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