Workflow Rule not sending email

I am trying to setup a workflow rule to fire off emails to users at at a predetermined time to remind them to make contact with a target or lead. For some reason when the conditions are met the rule says it executed successfully but no email was sent.

My setup:
SuiteCRM 7.9.4
Installed on Local network dedicated machine
Used by machines on Local Network
Installed on Debian 8 Jessie
Email server used for for relay is dedicated local machine

Before you ask:
I have inserted the proper command in the Crontab for www-data
I have verified all permissions are appropriate for the installation (www-data)
I have done a Quick Repair and Rebuild
I have also done Rebuild Schedulers
All of the Schedulers listed indicate that they have never been successfully run (even after using SuiteCRM for a year and a half)