At issue is that, right now, New Outlook is asking for every.single.email with graphics to be trusted. That approach is totally ridiculous. In classic outlook, the user can take on the possible risk of malware embedded in graphics. However, New Outlook seems to think that such an approach is not an option anymore. It will take years before "senders" are trusted; I get emails from clients, magazines, etc. The list is never-ending. I can't continue to be bothered with having to "trust this sender."
So, this is yet another black eye for the New Outlook. Not only does it not support S/MIME or a unified inbox (like Mac's, iOS, and Android) or even allow for searching globally (you can only search on "current mailbox"... OMG), but it is treating the user as an ignoramus. MS needs to address all these if they ever want people to positively adopt the New Outlook.