What software are you using to encrypt your sensitive emails?
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If your using Office365 you can add encryption but its a little clunky to use. As Theo Soumilas suggested MailProtector is much simpler to use and is easy to set rules to prevent info that should be protected from slipping through the cracks. It also allows large file transfers, automatic notification of messages being opened, prevents the forwarding of the message without your approval..lots more features.