So you have found yourself in the position of moving to Exchange Online from a legacy version of Exchange Server, namely Exchange 2010. You are planning to move everyone, or mostly everyone to Exchange Online and directory synchronization plays a major part (can it play a minor part?) in your plans. So you have made the option to go hybrid mode when you discover that there are manual steps to making Exchange 2010 mail flow to Exchange Online work if you have Exchange Edge Servers in use.

So, what do you do. You look online and find a number of references to setting up XOORG, but nothing about what that is and nothing about what you really need to do. And this you found this article!

So, how do you configure Exchange Server 2010 with Edge Servers, so that you can have hybrid mode to Exchange Online.

Why You Need These Steps

So you ran the hybrid wizard, and it completed (eventually if you have a large number of users) and you start your testing only to find that emails never arrive in Office 365 whilst your MX record is still pointing on-premises. After a while you start to get NDR’s for your test emails saying “#554 5.4.6 Hop count exceeded – possible mail loop” and when you look at the diagnostic information for administrators at the bottom of the NDR you see that your email goes between the hub transport servers and the edge servers and back to the hub transport servers etc. and about three or so hours after sending it, with the various timeouts involved, the email NDR arrives and the message is not sent.

The problem is that the Edge Server sees the recipient as internal, and not in the cloud, as the email has been forwarded to the user@tenant.mail.onmicrosoft.com, and Exchange 2010 is authoritative for this namespace. You are missing a configuration that tells the Edge that some emails with certain properties are not internal, but really external and others (those coming back from the cloud) are the only ones to send internal to the on-premises servers.

So what do you do?

Preparation

Before you run the hybrid wizard you need to do the following. If you have already run the wizard that is fine, you will do these steps and run it again.

1. Install a digital certificate on all your Edge Servers that is issued by a trusted third party (i.e. GoDaddy, Digicert and others). The private key for this certificate needs to be on each server as well, but you do not need to allow the key to be exported again.
2. Enable the certificate for SMTP, but ensure you do not set it as the default certificate. You do this by using Exchange Management Shell to Get-ExchangeCertificate to key the key’s thumbprint value and then running Enable-ExchangeCertificate –Thumbrint <thumbprintvalue> –Services SMTP. At this point you are prompted if you want to set this certificate as the default certificate. The answer is always No!
3. If you answer yes, then run the Enable-ExchangeCertificate cmdlet again, but this time for the certificate thumbprint that was the default and set the default back again. If you change the default you will break EdgeSync and internal mail flow for everyone. And you must use the self-signed certificate for EdgeSync and this third party issued certificate for cloud mail flow, as you cannot use the same certificate for both internal and external traffic.
4. The certificate needs to be the same across all your Edge Servers.
5. If you are doing multi-forest hybrid, then the certificate is only the same across all the Edge Servers in one Exchange Organization. The next organization in your multi-forest hybrid needs to use a different certificate for all its Edge Servers.
6. Then take this same certificate and install it on a single Hub Transport server on-premises. The hybrid wizard cannot see what certificates you have on the Edge Servers, so you need to help the wizard along a bit. Again, this certificate needs enabling for SMTP, but not setting as the default certificate.

Running The Hybrid Wizard

Now you can run the hybrid wizard. The important answers you need to include here are that the hub transport server that you pick must be the one that you placed the certificate on, as you cannot pick the Edge Servers that you will use for mail flow in the wizard. But you will need to enter the IP addresses that your Edge Servers are published on the internet as, and you will need to enter the FQDN of the Edge Servers as well.

Complete the wizard and then time for some manual changes.

Manual Changes

The hybrid wizard will have made a send connector on-premises called “Outbound to Office 365”. You need to change this connector to use the Edge Servers as the source servers. Note that if you run the hybrid wizard again, you might need to reset this value back to the Edge Servers. So once all these required changes are made, remember that running the wizard again could constitute an unexpected change and so should be run with care or out of hours.

Use Set-SendConnector “Outbound to Office 365” -SourceTransportServers <EDGE1>,<EDGE2> and this will cause the send connector settings to replicate to the Edge Server.

Next get a copy of the FQDN value from the receive connector that the hybrid wizard created on the hub transport server. This receive connector will be called “Inbound from Office 365” and will be tied to the public IP ranged of Exchange Online Protection. As your Edge Servers receive the inbound emails from EOP, this receive connector will serve no purposes apart from the fact that its settings are the template for your receive connector on the Edge Servers that the wizard cannot modify. The same receive connector will also have a setting called TlsDomainCapabilities and the value of this setting will be mail.protection.outlook.com:AcceptOorgProtocol. AcceptOorgProtocol is the XOORG value that you see referenced on the internet, but it is really called AcceptOorgProtocol and this is the value that allows the Edge Server to distinguish between inbound and outbound mail for your Office 365 tenant.

So on each Edge Server run the following cmdlet in Exchange Management Shell to modify the default receive connector: Set-ReceiveConnector *def* -TlsDomainCapabilities mail.protection.outlook.com:AcceptOorgProtocol -Fqdn <fqdnFromTheInboundReceiveConnectorOnTheHubTransportServer>.

This needs repeating on each Edge Server. The FQDN value ensures that the correct certificate is selected and the TlsDomainCapabilities setting ensures you do not loop email to Office 365 back on-premises again. Other emails using the Default Receive Connector are not affected by this change, apart from now being able to offer the public certificate as well to their inbound partners.

You can now continue with your testing knowing that mail flow is working, so now onto AutoDiscover, clients, free/busy, public folders etc. etc. etc.