Routing email from 365 to a subdomain

Anonymous
2020-12-01T17:51:01.487+00:00

We have begun migrating to Office 365 from Exchange and are currently in hybrid with some users migrated but most not. We have a routing situation that I am struggling with and hoping for assistance.
In Exchange on-prem we have a subdomain defined as an internal relay domain called bot.company.com. The reason for this is we have custom bot running on a server that we have to be able to send certain emails to for custom processing. In Exchange we have a send connector that routes emails addressed to anything ending in @Bot .company.com to a smart host, which is the server running the bot. This has been working fine.

We now need to be able to send to it from 365. I've added the domain to 365 as an internal relay domain and created a send connector that points directly to the bot server as a smart host. However, when I send to it the email goes to the on-prem Exchange server and not the bot server. The Exchange server then routes to the bot server, so it is working, but it does not appear to be using the send connector I created.

Can someone advise me on the correct way to set this up? Do I even need a send connector in 365 and, if so, how would I get it to send directly to the bot server instead of to Exchange first?
Thanks

Microsoft Exchange Online Management
Microsoft Exchange Online Management
Microsoft Exchange Online: A Microsoft email and calendaring hosted service.Management: The act or process of organizing, handling, directing or controlling something.
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Exchange Server Management
Exchange Server Management
Exchange Server: A family of Microsoft client/server messaging and collaboration software.Management: The act or process of organizing, handling, directing or controlling something.
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Accepted answer
  1. Andy David - MVP 147.9K Reputation points MVP
    2020-12-03T19:13:42.723+00:00

    The issue there however is that with Centralized Routing enabled, you are telling EOP to route all mail through your on-prem Exchange Servers. in other words, this is by design.

    If you were to change HCW to use the standard routing, it would work as expected.

    https://learn.microsoft.com/en-us/exchange/transport-routing


1 additional answer

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  1. Lucas Liu-MSFT 6,176 Reputation points
    2020-12-02T06:45:53.537+00:00

    Hi anonymous user ,
    Please try following steps to create a connector and transport rule.

    1. First create a new connector, please select the “Only when I have a transport rule set up that redirects messages to this connector” and then specify FQDN or IP address of the smart hosts, then define your TLS settings depending on your security needs.
    2. Then create a new transport rule, click “More optinos….”, for “Apply this rule if…, select The recipient… and domain is, then specify the domain you want to send. For “Do the following…”, choose Redirect the message to… and specify the following connector, then choose the specific outbound connector you want to using.
    3. After completing the above operations, please try to send a test email to see if the email is sent directly to the bot server through a specific outbound connector.
      For the specific steps you could refer to: Scenario: Conditional mail routing in Exchange Online.

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