My customer has numerous devices that send e-mail via an SMTP server (printers, phone system, etc.). Those devices don't support encrypted connections. The customer moved from onsite Exchange to Office 365, so these devices don't have a local e-mail system any longer. How do I setup Windows Server 2008 R2 SMTP relay to forward e-mail from these devices to Office 365 via an encrypted connection? The following articles are close, but don't quite get all they way there. http://fmuntean.wordpress.com/2008/10/26/how-to-configure-iis-smtp-server-to-forward-emails-using-a-gmail-account/ http://www.itsolutionskb.com/2008/11/installing-and-configuring-windows-server-2008-smtp-server/ For example, when I test the gmail solution, I get an Invalid Address error when testing this via telnet at the rcpt to: command. Thanks in advance.

Hello, for Office365 please use the following forum: http://community.office365.com/en-us/f/default.aspxBest regards Meinolf Weber Disclaimer: This posting is provided "AS IS" with no warranties or guarantees , and confers no rights.

Please re-read the question. It's an Windows Server 2008 R2 question. The basic question is: How do you setup an SMTP relay in Windows Server 2008 R2 to take local unencrypted SMTP e-mail's and relay them through an encrypted link to another smtp server? This includes knowing the correctly SMTP gateway, port number, Authentication, SMTP login and password, and POP settings to use on the device that is accessing the gateway. It has nothing to do with Office 365, except that adopting it has caused the need. I'll remove it from the title.

Hi, SMTP clients can connect to Exchange Online SMTP servers and authenticate using Microsoft Online Services user credentials to send mail. The connection requires Transport Layer Security (TLS). SMTP Relay capability allows organizations to use Exchange Online as an SMTP service for mail originating outside of the Exchange Online environment, for example SMTP-enabled applications such as fax servers. Using SMTP Relay with Exchange Online: http://blogs.technet.com/b/msonline/archive/2009/09/02/using-smtp-relay-with-exchange-online.aspx If you want to setup SMTP relay on your window 2008 server, please take a look at the following article: Configure SMTP E-Mail in IIS 7: http://learn.iis.net/page.aspx/751/configure-smtp-e-mail-in-iis-7/ If you have more question about SMTP relay with Exchange Online, you'd better ask your question at http://social.technet.microsoft.com/Forums/en/onlineservicesexchange/threads If you have more question about SMTP relay with IIS, you'd better ask your question at http://forums.iis.net/default.aspx?GroupID=41 Thank you for your understanding. Best Regards, James

Ok, I have the SMTP Relay setup and it works when testing from telnet on the server running the smtp relay. However, it still doesn't work from the printer. The printer asks for the following and my answers are included: Primary SMTP Gateway: <servername is what I type - it resolves correctly to the ip address> SMTP Port Number: 25 <same as when using telnet> E-Mail Send Authentication: < I don't know what to enter here. It's a drop down with the following choices: POP before SMTP (Plain), POP before SMTP (APOP), SMTP AUTH (Plain), SMTP AUTH (Login), SMTP AUTH (CRAM-MD5), CMTP AUTH (AUTO) ) SMTP Login User: <valid user@domain.com> - I really don't what The SMTP relay is using this for. I'm allowing anonymous access. SMTP Login Password: <password> POP3 Server Address: <servername> - For POP, does the SMTP relay provide a pop login? I use the same server name as for SMTP above. POP3 Port Number: <110> POP User name: <valid Server username> POP Password: <valid password> Reply Address: valid address What does the SMTP Relay expect for these? Thanks.

Thank you. I figured it out. The printer has an odd Authentication setting of Unkown, that has to be used. In addition I have to setup an external domain that is used by Office 365. This Office 365 SMTP blog post has a detailed answer.

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