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RyanH's avatar
RyanH
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Nov 05, 2025

F5 breaking Exchange authentication

We have Exchange 2016 going through our F5 BigIP. It works nicely. When we add our new Exchange 2019 server, clients are unable to authenticate using the desktop version of Outlook. Auth works fine without the F5 in the loop.  Thanks in advance for any thoughts you might offer as our team as well as F5 support are stumped. 

5 Replies

  • Did you configure the F5 with any SSL bridging? I saw some issues with Exchange Extended Password Protection in the past that would cause issues with failed authentication. 

  • Indeed, if you have enable Extended password protection on exchange and SSL bridging on F5 you will face issues as it is not supported.

  • The issue will come if you have oneconnect profile or you created the application using iAPP. or If possible, use SSL bridging (client→F5→Exchange all over HTTPS).Disable Server Name Indication (SNI) on the server SSL profile if your Exchange servers don’t support it. Also Disable HTTP/2 . try this things and verify if the issues are resolving or not.

     

    BR
    Aswin

  • Hello RyanH​ 

    Thanks for posting to our community! I noticed that you got a few responses and stated you had contacted support, if you were able to get a resolution I would like to encourage you to update your post and mark as solved. However, if you have not please let me know. 

    -Melissa 

  • RyanH's avatar
    RyanH
    Icon for Nimbostratus rankNimbostratus

    Just wanted to close the loop on this- We ended up converting from iApp rules, to the newer FAST templates.  Still no luck. Tried testing with SSL bridging disabled, no luck. Finally took our webmail SSL cert and put that on the F5, and it all worked. I can't really explain it, I'm just happy it's working. Thanks for all the replies.