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When performing a batch update (e.g. an update that affects 20 records), Salesforce bundles this up into a single outbound message with each notification as an object in a list.

Is there anyway to prevent this i.e. have Salesforce send one outbound message for each update/one notification per outbound message?

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The bundling of the message is done for the performance reasons (Being multi-tenant Salesforce has to be always cognizant about performance). Currently there is no way to disabling this behavior.

You could handle it and break yourself into single messaging by writing some extra code in your system or adding a middleware in the system that is consuming if it is too rigid for a change.

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