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Use Exchange Online for sending smtp e-mail from on premises devices like printers

Posted on 2015-02-12
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Last Modified: 2015-02-13
I migrated to Exchange Online. There is no on premises e-mail server anymore. I would like to use Exchange Online to send e-mail log messages from devices on premises.

I'm looking for options, advice and tips to get configurated, up and running, using Exchange Online.
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Question by:NicoNL
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Damien Kay earned 500 total points
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First, you can view the documentation here:  https://technet.microsoft.com/en-us/library/dn554323.aspx

If all the recipients in the local application are Office 365 users, and you have a static external IP at your Client's  location, then you do not need to use any authentication to use the Relay Options.  Simply choose the options in the first column in the article mentioned above in the first answer.  

Follow the instructions to find the "FQDN of SMTP Endpoint" or "string" for your domain.  It is the same as your MX record, and it should look something like "domain-com.mail.protection.outlook.com." It responds on Port 25, without any authentication, as long as the email recipients are using Office 365, and as long as you do not have a dynamic external IP address.

I usually create a CNAME in DNS that points the name "smtp.domain.com" to the longer name above, as that makes it easier to remember and to use on applications and even "scan to email" devices inside an organization.

If you need to send email via SMTP to users OUTSIDE the O365 organization, then you will need to follow the instructions in the second column, which require a licensed account.
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by:NicoNL
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Hi Damien,

I was reading this article yesterday, but the problem with the SMTP Relay option is that a dynamic IP address isn’t supported or allowed. We have 2 static public IP addresses (NLB redundancy) for internet access, depending on the firewall the user is connected to for NAT access to the internet. I can't enter 2 IP addresses into the connector.

When using the client SMTP Connection option, then valid Office 365 user credentials must be passed. Not all devices have the option to enter the user credentials for authentication and support only port 25, even no TLS.

So that leaves me with option Direct Send. I'm testing this option with a SMTP server, but haven't been able yet to get Direct Send to send e-mails.
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by:NicoNL
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I got SMTP Relay working. The missing link were smtp server mail.o365info.com and smarthost pod51014.outlook.com.
http://o365info.com/smtp-relay-in-office-365-environment/

And of course "The option of installing IIS server as a mail relay on a Windows 2003 server is not supported because the Windows 2003 server cannot support encryption of 256 bit"

Thanks :-)
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