So that is going to be AT&T and Blackberry he likely was pulling my mail from

 Which is actually pretty interesting since he would exploit Apple Machine learning voice processing later. Also someone would encourage me to go back to using Blackberry for messaging in 2013.

Obviously strange I would have a message "sent from my iphone" when I had a blackberry. I'm going to have to sleep and revisit where this error is. 

 

This is a LOT of email to have to revisit and sift through. 

 

This is even more strange.... I doubt I was even noticing as tending to my personal email was secondary to work.

 

I don't recall this convo cannot be sure though. That was a long time ago. I do not have sent items in this file.