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Outlook connecting to O365 18.0.4 MR4

Brian Straka

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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  • in reply to Brian Straka +1 verified

    If anyone is wondering, it appears that Microsoft in its infinite wisdom has made Outlook depend on WINS in some fashion.  In my SSL VPN settings on the XG, I put my DNS servers IPs (which are also my domain controllers and WINS servers internally) in the WINS section of the config and voila, Outlook connects again.

    Don't know why or how but seriously I can not understand how I am the only one with this issue and it took 2 weeks of putzing around to figure it out. Hopefully this answer helps some other poor soul out in the future

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