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Trying to create email workflow to send to external clients

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I'm stuck on creating this query. I realized after starting that I cannot send email addresses from workflow if contact not in CRM. So, I added Contact 1,2,3 etc to my new case form to pull from the Contact lookup form so the email address pulls from there. The other step is that I need this field called "Client Email Update Sent" to trigger the email workflow when it is set from No to Yes.

Upon creating this workflow, it only allows me to select when Record is created option, not when record status changes. Unless I am understanding that option wrong. The contacts will be added sporadically, not guaranteed they will all be added when the case is first opened. I created a test person with my own email listed and I cannot get it to generate. Please help! I dont understand what I am doing wrong.


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