I've run into this workflow problem before, but it happened again so I'm sharing.
We have a standard.
No passwords in plain-text. If passwords need to be emailed, the email will be encrypted with S/MIME.
Awesome. I have certificates, and so do my coworkers. Should be awesome!
Subject: Anti-spam appliance password
[The content can't be displayed because the S/MIME control isn't available]
Standard folowed, mischief managed.
Subject: RE: Anti-spam appliance passwordThanks! Worked great.
From: meuid: admin1792
Encryption is hard. It would be awesome if a certain mail-client defaulted to replying-in-kind to encrypted emails. But it doesn't, and users have to remember to click the button. Which they never do.