Set up SMTP Relay for Office 365 with Windows Server 2008 R2

Install Internet Information Services (IIS)

Add Roles > Next > Web Server (IIS) > Install > Select the following

ODBC Logging,
IIS Metabase Compatibility,
IIS 6 Management Console

Install SMTP server role

Add Roles and Features > SMTP Server >


Setup SMTP

Start > Administrative Tools > Internet Information Services (IIS) 6.0 > SMTP Virtual Server > Properties


Advanced > Add > enter IP address > OK


Under Access tab, ensure Anonymous Access is selected

On Connection, ensure Only the List Below is selected

On Relay, ensure Only the List Below is selected

Delivery tab > Outbound Security > Basic Authentication > enter Office 365 account name and Password > TLS Encryption


Outbound Connections > TCP 587 > OK


Advanced > specify as Smart host > OK > Restart SMTP services



Test by dropping Email.txt with the following content at C:\InetPub\MailRoot\Pickup\ folder.

SUBJECT: Test email in the subject line


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