Automated Email when rows are added or changed - email not sending properly


I have a workflow setup to email anyone in the Assigned To column when a row is added or changed on a sheet. We duplicate these sheets each month and add new rows with new assigned to contacts for each row.

The issues is that not all assigned to contacts are receiving the email through the workflow. The workaround we've found is that we have to add all other row info, save the sheet and THEN add the assigned to contact name and save again. This seems to recognize the new assigned to value as a change and sends the email properly. Any advice on how to get around this multi-save step? I've attached a screen shot of our workflow and sheet setup for reference.