troubleshooting Question

Design Question: Office 365 + Exchange 2016 Hybrid

Avatar of Edward Cho
Edward ChoFlag for United States of America asked on
Microsoft 365Network ArchitectureExchangeEmail Servers
5 Comments3 Solutions623 ViewsLast Modified:
Hello All!

I was wondering if any expert minds had a better way to do this.  We want to have this setup in our environment:

Capture.PNG
The only issue is that the amount of IPs required to pass through the firewall under Exchange Online at this URL is quite large.  Adding it to both the connector on our on-prem exchange server and firewall makes it extremely messy.

The reason we desire this flow is for our signature software (CodeTwo Exchange) that stamps everyone's outbound e-mail with the standard signature.  We also have journaling but that doesn't affect it either way.  

We currently have it setup so that the Office 365 mail is going right to Proofpoint (as a test).  It makes firewall rules+connector whitelisting much easier but there are issues with internal e-mails being tagged as phishing e-mails + signature issues.  

Any ideas/tips & tricks would be much appreciated.
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