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akashg88's avatar
akashg88
Copper Contributor
May 02, 2019

Hybrid mail flow with IronPort

Hi, One of my customer has the following setup, and I'd need some recommendation to setup a hybrid mail flow -   Incoming emails - Internet -> Cisco ASA firewall -> on premise Ironport -> Exchang...
exchange
hybrid
migration
office 365
NunoAriasSilva's avatar
NunoAriasSilva
MVP
May 02, 2019

Hi akashg88 

 

Is not advised by Microsoft to have any device between Exchange and Office 365, but you can setup hybrid and change de Connectors, both on-premises and Online to point to your infrastructure, but for best security you must enable TLS on those devices and Exchange Online and OnPremises Connectors.

  • akashg88's avatar
    akashg88
    Copper Contributor
    May 02, 2019

    Hi NunoAriasSilva 

    Thanks for your response - I agree that there shouldn't be any device and I am trying to figure out a way to bypass Ironport, but unable to do so. 

     

    Is there a way by which I can bypass Ironport considering that traffic on firewall for port 25 is NATed to go to Ironport first. How do I bifurcate the traffic ?

    NunoAriasSilva wrote:

    Hi akashg88 

     

    Is not advised by Microsoft to have any device between Exchange and Office 365, but you can setup hybrid and change de Connectors, both on-premises and Online to point to your infrastructure, but for best security you must enable TLS on those devices and Exchange Online and OnPremises Connectors.

     

    • Spiros Karampinis's avatar
      Spiros Karampinis
      Brass Contributor
      Jan 15, 2020

      akashg88 please have a look at the following post from Cisco

       

      https://www.cisco.com/c/en/us/support/docs/security/cloud-email-security/214812-configuring-office-365-microsoft-with.html

       

      Could that help you solve your issue ?

       

      Kind regards

      Spiros

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