19. January 2013 · Comments Off on Setup Windows Server 2008 SMTP Relay for Office 365 · Categories: Office365 · Tags: , ,

Many small businesses have printers that scan to e-mail, phone systems that send e-mail status updates, and a number of other e-mail enabled applications and devices.  When converting to a cloud based e-mail system, like Office 365, sometimes these devices cannot be configured to send e-mail over encrypted links to the cloud.  Office 365 required an SMTP connection that supports TLS encryption and many legacy devices or applications don’t support this.

The solution is to install an onsite SMTP relay that supports an encrypted connection.  Fortuneately, Windows Server supports an SMTP relay for Office 365.

This how-to guide assumes you have an operational Windows Server 2008 server within your company / organization.  It will work through adding the correct roles and features to Windows Server 2008, and then configuring them for communicating with Online Exchange within Office 365.

Determine Office 365 SMTP Server Settings

Before you can configure the relay, you must know the exact mail server addresses to use in Office 365.  To determine those, follow these steps:
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