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

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.