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I have a SPD 2013 workflow on a list that has an App step in which it creates a List Item on a Targetlist in a different Site Collection using the Call HTTP Webservice action with HTTP Post to create a new List Item.

Item creation works like a charm. But the Targetlist has a workflow which triggers after new item is created, which doesn't seem to get triggered if I use the REST API to create a new item.

Do I have to set some flag in the request to trigger "on item creation" workflows? Or is there another solution to this?

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Workflows wont be triggered by system accounts by default. The app step has no user linked to it, so I guess it will have a hard time starting an workflow also. Since the workflow needs to rehydrate the user from the UPA it will have a hard time doing so with an app principal.

Try to verify this be relaxing the permissions and creating an item in a user context instead of an app step.

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In alternative you can start SharePoint designer workflow using REST API. Go through below link.

http://www.benprins.net/2016/12/30/sharepoint-2013-workflow-start-a-workflow-using-a-rest-call/

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