Mail flow issue from exchange to Office 365 (exchange online)

Nur Hossain 282 Reputation points
2020-11-23T07:29:50.067+00:00

In our exchange environment, we have three mailbox server in MZ zone and Symantec Messaging Gateway (SMG) and PGP (for Encryption) as email security appliance. After enable exchange hybrid, we facing issue while sending mail from exchange to office 365 (exchange online). In our exchange server we allowed internet through proxy that's why we are unable to route mail from exchange to office 365 directly. So, we try to route through SMG but loop luck (Loop detected).

Recently , we deploy Edge server to route mail from exchange to office 365 but always mail goes to SMG. mail not routing through EDGE.

Any Idea?

Note: Others mail flow working as expected.

Our mail flow diagram:
41815-prime-bank.png

Looking for help.

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.
7,626 questions
Microsoft Exchange Hybrid Management
Microsoft Exchange Hybrid Management
Microsoft Exchange: Microsoft messaging and collaboration software.Hybrid Management: Organizing, handling, directing or controlling hybrid deployments.
2,097 questions
0 comments

1 answer

Sort by: Most helpful
Most helpful Newest Oldest
  1. KyleXu-MSFT 26,261 Reputation points
    2020-11-24T01:52:57.477+00:00

    @Nur Hossain

    We don't know how the SMG works. Does there exist send connector on your Exchange server to send emails to that application? If so, try to remove that send connector. You need to prevent outgoing email through the left part, make all you outgoing email through Edge server rather than "Exchange on-premises → SMG →PGP → Internet"

    There only can exist Edge server between Exchange on-premises and Exchange online. So, if email through the left part, it will cannot send to Exchange online. You can try to add your application before the EOP, if they are supported.
    42017-qa-kyle-09-50-22.png

    If the response is helpful, please click "Accept Answer" and upvote it.
    Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

Your answer

Answers can be marked as Accepted Answers by the question author, which helps users to know the answer solved the author's problem.