![]() ![]() It's ONLY other government clients that results in this endless looping. Emails from migrated mailboxes to non-government O365 also works fine (O365 -> Barracuda -> O365). Emails from on-prem to non-government O365 orgs works fine (Exchange -> Barracuda -> O365). Those messages go from Exchange -> Barracuda -> O365 -> Barracuda -> O365. The crazy thing is that this even affects on-prem users. The hops show that messages go from O365 -> Barracuda -> O365 -> Barracuda, etc. When sending outbound to another O365 government client, they get a rejection saying that there is an endless loop. In Barracuda, we've added Microsoft's Exchange IP addresses as allowed relay IPs. The recipient's domain is *, it requires TLS and the smarthost is the Barracuda's internet facing IP. I have set up an outbound mail connector, from O365 to Partner Organization. They are only budgeted for EOP1 licenses, so they can't use either DLP or OME in the cloud, so they have to rely on the Barracuda. ![]() ![]() They use the Barracuda for outgoing message encryption both for keywords and for DLP. Then, it goes one more hop to O365 for already-migrated-users. It goes from Internet -> Barracuda -> Exchange on-premises. They want to keep their on-premises Barracuda Email Gateway appliance for both inbound and outbound email flow.Ĭurrently, inbound mail flow works. I am working with a government (non-GCC-High) client with an Exchange 2016 hybrid that is working great. ![]()
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