So, considering some of the pitfalls that come along with S/MIME and OME, you might not be champing at the bit to use either method. What about Encryption Add-ons for Outlook
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OME requires recipients to either sign in to an Office 365 account or confirm their identity via a single-use password, sent as a code to a mobile device or email account. Whilst sending encrypted emails via OME is straightforward, your recipients will have a bit of work to do to access the message. You will need a valid subscription, however, which can set you back a pretty penny. With Office 365 Encryption, you won't need any certificates to send encrypted messages.