@nerdydad said in O365 and MS's encrypted mail (portal):
Are these cox.net recipients repeat customers? If so, have you considered PGP keys between them?
LOL - they are spouses of the owners, etc, as well as customers. As mentioned in the OP about S/MIME, there is no chance the business, nor it's customers would deal with setting up a key exchange.
Hell, Edward Snowden barely go the journalist there to get a set of keys setup so he could trade messages with them, you really think you're going to get normal business people to do so? or house wives?