Since the Exchange 2010 HCW creates a new receive connector for Office 365 that is secured by the Exchange Online Protection (EOP) IP addresses, it’s important that the Exchange server sees the proper source IP for mail messages. Issue #2: Not Preserving EOP Source IP (Exchange 2010)
While this used to be a somewhat undocumented step, it has since been documented in the “ Exchange Server Deployment Assistant“. In Exchange 2003 environments, the Exchange 2010 HCW does not properly configure the hybrid routing domain ( ) this domain should be configured as “Internal Relay” as opposed to “Authoritative”. This issue will actually cause hybrid mail flow to fail to route. Issue #1: Incorrectly Configured Hybrid Routing Domain (Exchange 2010) If the header “ X-MS-Exchange-Organization-AuthAs” says “Internal”, then all is well if the header says “Anonymous”, you may have one of the issues below. The quick way to check is to look at a message received in each environment and check the message headers. So just like a conference room is not going to accept a booking request from a random Internet user, it won’t accept a booking from your cloud user if that message appears as external. It basically comes down to whether the messages between environments appear as “internal” or “external”. Issues booking conference rooms or receiving the wrong out-of-office message are also symptoms. If messages between environments occasionally end up in a user’s junk mail, that’s definitely a good sign there is a misconfiguration. There are a number of symptoms that might indicate that hybrid mail flow is not working properly even when messages are routing.
But My Mail Is Routing… So It Must Be Working If you’ve modified the connectors created by the HCW in an attempt to “make things work”, there’s a good chance you’ll want to delete them and let the HCW recreate them so you can identify the true root cause of your mail flow problem. In the cloud, inbound and outbound connectors are created and again the inbound connector uses a certificate instead of IP address for security. In this case, the “Default Frontend” receive connector is modified for hybrid mail flow and instead of using a list of IPs, a certificate is used to force hybrid mail flow. In the cloud, the HCW creates an inbound connector and outbound connector the inbound connector is scoped to the source IP you provided in the HCW.For Exchange 2013, the HCW creates an on-premises send connector called “Outbound to Office 365” but does not create a new receive connector.
There are some differences in how the configuration is setup in Exchange 2010 versus Exchange 2013 which is why you’ll see some issues on one platform and not the other.įor Exchange 2010, the HCW creates an on-premises send connector called “Outbound to Office 365” and an on-premises receive connector called “Inbound from Office 365” the receive connector has a list of the Exchange Online Protection (EOP) IP addresses on it so that messages from EOP use this connector instead of the default receive connector. These connectors, along with a proper network configuration, are the foundation of hybrid mail flow. Among other tasks, the Hybrid Configuration Wizard (HCW) creates send and receive connectors in the on-premises Exchange organization and in Exchange Online.
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A deeper look into the messages and you might find that while they are routing, they are not appearing as “internal”.īelow are some of the things to look for and how to resolve these hybrid mail flow issues.īefore we jump into identifying issues, it’s important to understand how hybrid mail flow is configured. In some cases, mail will actually be routing between organizations and it may seem like everything is working. If you spend any time browsing the Office 365 Community Forums, you’ll see a number of posts on this same issue.Įven if the Hybrid Configuration Wizard completed successfully, it does not mean that hybrid mail flow is setup properly. Part of this concept is that while you technically have two separate Exchange organizations, the mail flow between these organizations appears “internal” so that a message from a cloud user looks no different than a message from an on-premises user.Īs a consultant nearly 100% focused on Exchange Online migrations, I’ve come across a variety of situations where hybrid mail flow is not working properly. Exchange Hybrid, when configured properly, can provide almost seamless coexistence between Exchange Online and your on-premises Exchange environment.
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