One of my user wants to send encrypted messages to external vendor so he requested IT department that how he can do this? I have configured my Outlook from Files-> Options -> Trust Center Settings -> Email Security. Click on Encrypted Emails and select 'Encrypt contents and attachments for outgoing messages'. After that to check this settings I have sent test email from my mailbox to myself and my colleague and we are able to see that encrypted message properly. But when we are sending emails with attachment then we cannot see or open that email. What we have to check and configure on Exchange Server CAS Role as well as on client application Outlook to achieve this.
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How is your issue? If your issue has been resolved you could mark the helpful reply as best answer, or you could share your solution and mark it. Your action will be helpful to other people who encounter the same issue:) – Joy Zhang Jun 02 '21 at 02:45
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Based on my knowledge, ensure that each of your recipients has an email encryption certificate installed in Outlook (or other S/Mime compatible email application) at their end when you use this way to encrypt mails. If the message is sent, you can be fairly confident that the recipient has the required certificate to open your encrypted email.
Here's a detailed steps on encrypting messages in your way for your reference: Method 1: Using Certificates (S/Mime)
Joy Zhang
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