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Outlook connecting to O365 18.0.4 MR4

Hey, I have a support request open for this but I figured I would put it out here to see what I could get before my remote session next Monday.  When connected to SSLVPN through the XG I can not authenticate to O365 via ADFS using Outlook.  Skype for Business works, MS Teams works, One Note, and One Drive all work...  We are using IPS and SSL Decryption.  I have added in all recommended exclusions using Sophos' provided tar file which was uploaded to my system.  I have also added exclusions for Microsoft's second level domains as well as our ADFS URL's

There is nothing obvious in the logs AT ALL... What gives?  I am like 99.9% sure this is SSL related but even when I put a straight up open rule outbound with no filtering and SSL decryption disabled it STILL fails...

If I disconnect the VPN and open Outlook... BAM it fires right up.



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  • FormerMember
    0 FormerMember

    Hi ,

    Thank you for reaching out to the Community! 

    Did you configure split or full tunnel SSL VPN? If it's a full tunnel, did you apply any advanced filtering such as web and application control on VPN to WAN firewall rule? 

    Thanks,

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  • FormerMember
    0 FormerMember

    Hi ,

    Thank you for reaching out to the Community! 

    Did you configure split or full tunnel SSL VPN? If it's a full tunnel, did you apply any advanced filtering such as web and application control on VPN to WAN firewall rule? 

    Thanks,

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