I had a significant failure with my two e-mail applications, Microsoft Exchange and Apple Mail.  The problem started when a friend of mine retired from his job and I was told that I can no longer send him any e-mail to that business e-mail address.  I deleted his entry in my computer for that business address.  But, that was not the complete solution.  The problem with Microsoft Exchange and Apple Mail is when I wanted to send my friend an e-mail, I was presented with his home e-mail address and his business e-mail address.  Why?  The reason is that both mail applications, it seems, scans all the prior e-mail from my friend to find all his addresses.  These applications, it seems, fail to ONLY pull up the address from Contacts.  The solution that I came up with was to use both e-mail applications and do a search for all the mail from my friend.  I then selected only the e-mail that was addressed to his work and deleted all those messages. As a check, I performed a search for my friends name and Mac Mail was ok but Exchange was not.  Exchange showed a small warning that more e-mails could be on the server.   Exchange allowed me to view those messages and  I deleted them.  That seemed to be the solution.  It would be really nice for those e-mail applications to include an option to only show addresses to people that are within my Contacts application.  Now I did discover that Mac Mail does have an interesting option.  Go into Mac Mail > Settings > Rule > then make a rule to delete any e-mail from the person.  Next shows the menu options and correct answers:

Description:
If any of the following conditions are met:   From contains E-mail address of person.
Perform the following actions:  Delete Message.

Posted:  3-4-2023