How to digitally sign and encrypt messages using S/MIME (Exchange 2010)

  • Synopsis

    This guide will show you how to digitally sign and encrypt messages using S/MIME Secure Messaging with Exchange.
  • Applicable to

    All SherWeb hosted Exchange 2010 accounts.
  • Prerequisite

    • a SherWeb hosted Exchange 2010 account
    • Outlook
  • How to

    Exchange to External or vice-versa with Outlook:

    Note: S/MIME can be used to digitally sign and encrypt messages sent to or from Exchange. This feature allows secure email communication between sender and recipient and assures the recipient that the identity of the sender as well as the content of the message was not modified during transmission.

    1. Both users need to download a secure email certificate1

    IMPORTANT: When obtaining your certificate, you will need to specify the same email address you will be sending messages with.

    Note: Once the certificate is installed correctly, you will see it in your Outlook by going to Tools - Trust centre - E-mail Security.

    1. You now need to send a signed email to the other user and vice versa in order for them to be able to decrypt any encrypted emails you may send them. In Outlook, create a new message by clicking on New and then click on the envelope and bell icon in the Options section.
    2. Click on Security Settings, check the box Add digital signature to this message and then click on OK. smime2
    3. When the recipient receives the message in his Outlook, he will need to open the message, right-click on the name in the From: field and then click on Add to Outlook Contacts. smime3
    4. In the Contact section, they should see the Contact and associated Certificate.  smime4
    5. Both users may now send signed and encrypted emails between themselves by clicking on the envelope and bell icon or the envelope and lock icon, located in the Options section.  smime5

    Exchange Internal using Outlook Web Access:

    After following the steps above, you can follow these quick steps to send and receive mail between users on Exchange with SherWeb.

    1. Connect to Outlook Web Access.?

    2. Click on Options.
    3. Click on E-mail Security and then click on Download the Outlook Web Access S/MIME control. smime1
    4. A new window will appear. Click on Run.
    5. You now need to publish the Certificate to the GAL of both users. In Outlook, go to Tools - Trust Center - E-mail Security and then click on Publish to GAL... in the Digital Ids (Certificates) section.
    6. You may then create a new message from OWA and choose to sign and encrypt it when sending it to the other user.

    If you need further assistance, please do not hesitate to contact us.

    Foot notes

    1. Since you will be required to install a Secure Email Certificate obtained from an outside source, SherWeb does not provide support for issues related to missing or corrupt certificates on your machine. Please refer to your certificate issuer for support. This FAQ is for basic reference purposes only.
  • Keywords

    Secure Email, SMIME, Outlook, OWA
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