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Trouble With First Workflow

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This is my first attempt to make a workflow which has more than a couple steps and I cant seem to get it to work. This is for a generic SharePoint 2013 list. I've taken some online tutorials and watched some videos but none of them get me close enough to achieve what I'm going for. This is what I want the logic to be:

  1. When a new item is added by someone (we'll call them person X) begin the workflow.
  2. Immediately send an email to person Y with the details of the new item added
  3. wait until the "status" field has been changed
  4. Send an email to Z if status reads "approved" or "denied". Else (when the condition would read "Request more info") send an email back to X.
  5. If the approved/denied route is taken the workflow can end there, otherwise I want it to wait until the status field is updated again before the email is finally sent to Z.

This is what I have in SharePoint Designer:

When a new item is added the workflow starts and sends the first email however once I've updated the status on the list the workflow status shows it's still on Stage 1 and the workflow stays stuck there. What can I do about this?


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