Outbound connector

Question

I currently have had a hybrid setup for about a year using Exchange 2010. I have a barracuda spam firewall that my MX record is pointed too and that handles all inbound and outbound traffic. My office 365 setup has not been using an outbound connector and just sending mail directly from office 365. Recently I have a need where I need my office 365 users emails routed through the on premise barracuda however I am having issues with the outbound connector.  

I set my outbound connector to point at my Barracuda's public IP address. When I validate the connector it fails at the send email step. I am using an @gmail.com address and this account does in fact receive the authentication email from *** Email address is removed for privacy ***. If I enable the connector mail will not be send. It will sit as pending with the following.

Reason: [{LED=450 4.4.101 Proxy session setup failed on Frontend with ‎'451 4.4.0 DNS query failed. The error was: DNS query failed with error InfoNoRecords‎'};{MSG=};{FQDN=na01-internal.map.protection.outlook.com};{IP=10.1.14.27};{LRT=3/23/2016 3:00:50 PM}]

My question is has anyone had any luck with setting up their Hybrid configuration using their Barracuda to filter outgoing mail from office 365. 

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Answer 1

I could not get the connector to work with emails going outside the company. I ended up setting up a new connector using my barracuda as a smart house and used a rule that said for any emails leaving the organization use that connector. My office 365 outbound is now being filtered which was my main objective.

Answer 2

Hi Mike,

Thanks for your PM rely.

From the PowerShell output you provided, I see that both UseMXRecord and IsTransportRuleScoped are False, and SmartHosts is valid. Theoretically, this should work as well. But my suggestion would be that you re-run the hybrid configuration wizard and enable centralized mail transport in the wizard. By enabling it, emails will be routed to the on-premises Exchange server before being delivered. For more detailed information about centralized mail transport, you can see Transport options in Exchange hybrid deployments.

Moreover, about the integration between Barracuda and on-premises Exchange server, please visit our Exchange on-premises support forum for any relevant questions.

Regards,

Allen

Answer 3

Hi Mike,

Since it involves 3rd-party products, we might not be able to help you finally achieve your goal (our community members may share some relevant experience though). But at least we can check if all settings regarding Office 365 Exchange Online are correct. Please run the PowerShell command Get-OutboundConnector for the affected mail connector and send us the output. (including Format-List) I have sent you a private message to collect the PowerShell results, see it at https://community.office365.com/user/conversations

Besides, about the SSL certificate MihirNayak mentioned above, you replied “I am not using SSL for testing but yes”. Can you please clarify what you meant here in detail?

Thanks,

Allen

Answer 4

I am not using SSL for testing but yes. I get an error saying that says "The domain of the recipient is not configured as part of connector".

Answer 5

Hi Mike,

What i understand is, you want that outbound connector should send any emails from O365 to your on-premise server (barracuda server)

So, when you create the outbound connector you specify the domain name , your barracuda server fqdn - that has to be a DNS record in public DNS, also you should use TLS authentication in both end by using a SSL certificate including your barracuda server fqdn as SAN name.

Are you done with the above ?

Please respond.

Thanks