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Skype for Business Exceptions When Using SSL Filtering

Skype for Business is unable to sign in when SSL filtering is enabled. Does anyone know what exceptions need to be added to get it to work?



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  • Have you tried using the SOCKS proxy?

    Cheers - Bob

     
    Sophos UTM Community Moderator
    Sophos Certified Architect - UTM
    Sophos Certified Engineer - XG
    Gold Solution Partner since 2005
    MediaSoft, Inc. USA
  • We created an Exception to skip the URL Filter, Content Removal, SSL scanning, Certificate trust check and Certificate date check for the following URLs:

    ^https?://TENANT-NAME.onmicrosoft.com
    ^https?://[^.]*\.office.com
    ^https?://[^.]*\.outlook.com
    ^https?://[^.]*\.microsoftonline.com
    ^https?://[^.]*\.office365.com
    ^https?://[^.]*\.lync.com
    ^https?://[^.]*\.online.lync.com
    ^https?://[^.]*\.infra.lync.com
    ^https?://[^.]*\.office.net
    ^https?://[^.]*\.office.live.com
    ^https?://clientconfig.microsoftonline-p.net
    ^https?://nexus.officewebapps.live.com

  • Hi,

    does the exception list work for you?  Cause we have similar problems with skype for business.

     

    Regards

    Thomas

  • Hello,

    I've also tried this exception list, but it doesn't work for me.

    Has sombody another solution for this Problem?

    greatings

    Holger

  • It worked for us. You may want to monitor the web filter log to see what traffic is blocked. We noticed Lync 2013 could not handle SSL inspection as it needed to see Microsoft's certificate to function correctly.
  • This reply is not very timely, but I think it's always good to find updated (or at least additional) information when searching for solutions. I found this thread several times when searching for information on how to configure UTM 9 to allow Skype for Business traffic through from my home network (i.e., as a Skype for Business user/client).

    First, to allow Skype to sign in at all I needed to exclude any URLs associated with my employer's domain.

    ^https?://([A-Za-z0-9.-]*\.)?company\.com/?(.+)

    (SSL scanning / Certificate trust check / Certificate date check)

    After that I could sign in and send IMs, but as I found out later, Skype calls did not work. In trying to get calls to work, I built up the following list of exceptions based on observing the web filter log output.

    ^https?://[^.]*\.office365.com/?(.+)
    ^https?://clientlog.portal.office.com/?(.+)
    ^https?://[^.]*\.microsoft.com/?(.+)
    ^https?://[^.]*\.yammer.com/?(.+)
    ^https?://[^.]*\.office.com/?(.+)
    ^https?://xx\.xx\.xxx\.\d{1,3}/?(.+)

    (SSL scanning / Certificate trust check / Certificate date check)

    The last line where the x's appear, are actually numbers, but that is the IP pool for my employer's Skype servers, or at least that is what they appear to be to me (I am not an IT guy). For some reason these URLs were showing as IPs only in the UTM 9 web filter log, else they should/would have been covered by the very first exception, I would have thought. I also had to add some firewall rules for Skype traffic to the company specific IP range for services (TCP/UDP 50000:59999 / UDP 3478) before I stopped seeing dropped packets in the firewall log, but not sure if that was an absolute requirement. (Surely though, it couldn't hurt to not drop legitimate packets).

    I have tested this with a couple of voice calls, but have not yet tested a meeting with sharing. Also I should point out that I haven't gone back and tried to trim the scope of settings back to find the bare minimum set of exceptions that are needed, so this should just be treated as a rough starting point, or something else to try, for anyone running into the same or similar issues.

    Cheers.

    EDIT: The line ^https?://clientlog.portal.office.com/?(.+) seems to be redundant based on the fact I added ^https?://[^.]*\.office.com/?(.+) afterwards.

  • Great first post, Wayne - thanks and welcome to the UTM Community!

    Cheers - Bob

     
    Sophos UTM Community Moderator
    Sophos Certified Architect - UTM
    Sophos Certified Engineer - XG
    Gold Solution Partner since 2005
    MediaSoft, Inc. USA