{LED=451 4.4.397 Error communicating with target host. -> 421 4.2.1 Unable to connect -> SocketTimedout: Socket error code 10060

Niranjan T Pattana Shetty 286 Reputation points

Hi All,
We have a hybrid environment in our infra and all of our mailboxes are hosted in Office365, and we have mail-flow triggered from applications happen from On-Prem Exchange, and sometimes as seen in the question title, we receive such errors, not sure what could be the issue here.

Need some guidance on the same.

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.
7,001 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.
1,668 questions
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  1. Niranjan T Pattana Shetty 286 Reputation points

    Hi AndyDavid,
    Thanks for the advise, the issue was the application was using the UPN to route mails and UPN wasn't added into the aliases, so the above error was generated. Thanks again.

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