Hello @tboardman, I hope you are doing well today. I understand how helpful it would be for you if we can trigger multiple webhooks from one single automation rule. A few of our other customers have also written to us regarding the same in the past and I’d like to confirm this has been raised as a feature request to our product team. 

As of now, we can add only a webhook per rule but you can have different matching conditions to trigger another webhook in a separate rule.     

That said, we’ll be sure to keep you posted with updates in the furture. 

It appears we cannot execute a webhook AND a thread in a single automation. We have a scenario where we need to do both. However, if the ticket is created in the portal then only the first one executes - so if webhook is first it works and the email doesn’t send, and if the thread is first, then the webhook doesn’t execute. 
note - both execute just fine if the ticket is created directly w/in freshdesk.