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So I have created the following workflow.

When a person creates a new list item, the variable Approval Status is by default Pending. So once the list item is created, it send an email to who created the request letting them know that it has been submitted for approval.

Next, the workflow will create a Task to send to HR to either approve or reject the employees leave request. If accepted, I have it showing on a calendar view, and if not it doesn't show up on the Calendar.

Everything up to that works just fine.

For some reason, when it is changed to approved or rejected from Pending, it will not send either of the emails I have created to notify the employee of his/her approval rejection. Why is this

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The reason it is not working is because you need to add a "wait" statement. Because SPD is not understanding that it should wait for a response before exiting the workflow. I am adding how to do it below :-

Add parallel action and create a new Boolean variable

enter image description here

Please make sure to set the variable to exit the parallel loop To do this right click on the first parallel action < click on advanced properties like shown below :- enter image description here

and now set the completion condition to the variable you are setting to as yes enter image description here

and that's it !! Please mark as answer if this solved your issue

Hopefully this helped someone out there !! :)

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