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We‘ve been using S/MIME-based end-to-end email encryption at work for a long time now. It’s a bit of a hassle whenever new employees start, and every two years after that, but it’s manageable. Apart from that, it just works. Why is it never even considered by so many people?
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More importantly, why is no-one working on making it less of a hassle? I know it doesn’t encrypt metadata, but it’s still so much better than most messaging services, let alone unencrypted, web-based email from a security perspective.