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How Can I Get Office365 to Relay SMTP Message to Recipient Outside of My Network

Posted on 2015-02-09
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Last Modified: 2015-03-03
My company is using Hosted Exchange, via Office 365, for email services. I have a server that is co-located outside of our company network that needs to utilize SMTP to send emails to clients. I created an incoming connector in Exchange to allow relay of emails originating from the public IP of this server. If those emails are sent to an email address on one of the domains serviced by our Hosted Exchange, it gets delivered to the recipient. However, any emails sent by this server to a recipient not in one of our domains, simply disappears, and is never delivered. I even checked the SPF record for this domain, to ensure the IP address of the server is included in it. I have a feeling I am missing one simple step, yet for the life of me, I can't figure out what it is.
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Question by:jimstrickland
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Assisted Solution

by:footech
footech earned 500 total points
ID: 40599823
I believe the only way you can relay to other domains is to authenticate to O365 (and thus everything would appear to come from the account you authenticate as).
What we've done is to configure the SMTP server to send directly to other domains (and to specifically route emails for our domain to O365 servers).  Sounds like you've already got your SPF record set up for this.  If you do this, you just have to configure your A and PTR records as you would for any other email server which delivers to the internet.
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Accepted Solution

by:
jimstrickland earned 0 total points
ID: 40628858
Microsoft support has verified that I have everything setup correctly. They are trying to figure out what the problem is on their end. Fortunately, I have a plan b. I already subscribe to SendGrid for sending out marketing mass mailers. It turns out I can successfully SMTP through my SendGrid account to solve the issue. I have tested successfully.
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Author Closing Comment

by:jimstrickland
ID: 40641463
I am accepting both solutions because the expert comment from footech is technically correct. It should have worked. However, I am using a different SMTP service because Microsoft has acknowledged a problem on their end that they are still working to correct.
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