@Dashrender said in O365 and encrypted mail to other email systems:

I don't look at it as bleakly as you do. You in no way told the receiver they couldn't receive it, you told them they have to use a different method to receive it. Is it a good experience - I'm not going to argue that point, frankly I don't care as long as it works.

But you did... you sent them an email and the email didn't include the payload, it told you to go look in another system for the payload that didn't arrive (the princess is in another castle.) Why did you need the email if email isn't delivering the message? It's obviously similar to failure... two systems are being used for a single thing. All they want is the payload, not a message telling them about a payload elsewhere.