Encrypted Secure Email in Office 365

So you’ve rolled out email, yay! But have you enabled your users to send secure encrypted email?  It is a very underused feature among small- and medium-sized businesses.  This makes me kind of sad because every business sends some personal data that should be protected. Quotes, bids, specifications, drawings, credit card information, health questions, benefits, or employment information, if sent via email should be sent in a secure manner.

Office 365 Message Encryption FAQ

How To Forward Office 365 Email Address To External Address Without A Mailbox

Office 365 default E-mail address using ADSI Edit when using DirSync

Open ADSI Edit

Navigate to User

Right-click on Properties

Navigate to proxyAddresses or if Exchange Schema is loaded msExchShadowProxy

Add or correct   ->    SMTP: <email address is added> 


Apply the changes and force a DirSync to Office365 Azure AD

See the article: 

Scheduled task PowerGUI and E-mailing PowerShell Scripts

Diagnosing E-mail Issues include SMTP auth

Step #1 - Check to see if your server is responding on port 25

You should repeat this test at least twice - once from the Modus server and once from another PC on the same network or, ideally, from a machine outside of your network (via a dialup or high-speed connection)


Extracting Email Header Information

Configure Sendmail as a Smarthost and rewriting the from-address

  1. Install both the sendmail and sendmail-cf packages on your Redhat/CentOs server.  Use the command: yum install sendmail sendmail-cf 
  2. To automatically start sendmail to start on system boot we issue the command: chkconfig sendmail on 
  3. To start sendmail NOW we issue the command: service sendmail start 
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