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Is this even possible?

Example: Department is a Child of Account.

The UI Wizard only includes Department fields on outbound message selector.

Found this link

Is there a way to manually edit the outbound message definition to do this?

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No this is not currently possible, you'd have to use the option to send a sessionId in the message and have your listener make an API call back to saleforce to get the related records it needs.

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