The thing is, most websites already know how to workaround that particular issue (https://news.ycombinator.com/item?id=42804447), so when users notice that something breaks with just your service and not everyone elses, you can say "Outlook is shit" all you want, the users will blame you for it, since you weren't able to fix what others could, for better or worse.
> You could roll over and decrease your security so that MS can claim they increased theirs
What part of your security would decrease if you "roll over" and what exactly does "roll over" entail here? Websites who've dealt with this issue implemented what I linked to above, they're no more/less secure than the website who didn't manage to work around this issue, they're just less buggy for Outlook users, if anything.