Bob McConnell wrote:

> These will be targeted emails for selected recipients, primarily in
> the Security and Public Safety offices. But they will be sent via
> public mail servers, so the content must be protected.

The question is - to what extent?  You can use TLS for server-to-server
encryption, which is easy, but if you need person-to-person encryption,
I think your best option is still S/MIME. 

> Knowing the first site where this would go for field trials, I suspect
> most recipients are using some version of Microsoft Outlook. But other 
> sites down the road are likely to have different clients. That end is
> completely outside of my control or influence. 

Use S/MIME.  It's standard, and it's supported by e.g. both outlook and

Per Jessen, Zürich (18.1°C)

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