I have many things that I think are going on but no sure what the problem may be.
Problem: Created a workflow in SharePoint Designer 2013 to send an email when something is added to a list. Then I added a pause to wait until an column changes to "Done" and another email is sent. The problem is that the initial email is not been sent to the person assigned person all of the time. It sometimes sends and other times doesn't. When I look at the workflow status for the items where the assigned person never received the email - the workflow reads "in-progress" with no errors. To me that shows that the email was sent and now it's waiting for status column to be "Done". But that is not true. The workflow may be "in-progress" but did not send the initial email. Again this is not consistent. Sometimes it works and other times it doesn't. Also, it doesn't work more with a particular assigned person that others.
What I tried: To try to fix the issue or figure out what's going on I have checked the workflow history. There are over 1,000 items in the history. Not sure if this is causing the issue. I have also check to make sure those being assigned have the proper permissions to the page. I also checked the error logs. Nothing.
Can anyone help me with this? I am not sure if it's a looping issue since I am using "Pause" but this the initial email that should be sent when a new item is added to the list.