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Microsoft Autoupdate on Mac now fails

Rogue

All,

I've been running 9.3 (9.355-1 currently) for a while now for the most part trouble free, but just ran into a slight issue. I have an Office 365 Sub on my Mac and obviously it's a good thing to update here and there. So I tried it out and found out that it can no longer connect, although interestingly enough I see 30 megs of traffic even though my Mac isn't showing any progress.

As it turns out I needed to completely disable Web Filtering before it would work! Normally I run in Transparent mode with full decryption enabled and like I said this has been fine up until a few weeks ago. I even tried to disable decryption and told it not to proxy https, neither of which worked. Looking in the LiveLog I'm not really seeing anything obvious sticking out..

I also tried disabling all other UTM services, the only one that fixed it was Web Filtering.

Funny enough Windows 7 Update works just fine!

So it seems that either some update to UTM broke things, or something happening on the Microsoft side isn't playing nice now.

Oh, and I do have a bunch of Microsoft specific Web Filtering Exemptions added which came from this forum, I'm wondering if something needs to be tweaked in there?

Just curious if anyone has any ideas..

Thanks much!



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  • 0

    Show a line from the Web Filtering log where a download has failed.

    Cheers - Bob

     
    Sophos UTM Community Moderator
    Sophos Certified Architect - UTM
    Sophos Certified Engineer - XG
    Gold Solution Partner since 2005
    MediaSoft, Inc. USA
  • 0 in reply to BAlfson

    That's the thing, I'm not really seeing much of anything in the logs saying it's having a problem, it just doesn't work..

    I disabled filtering the other day and let run so I'll need to wait for the next bunch of patches to be released to troubleshoot again.

    Do you have any other suggestions for which logs to check, or any other debugs I can enable? Or just check the web, IPS, firewall logs?

    Thanks much!

  • 0 in reply to Rogue

    Sometimes, even though the line shows that the access passed, the browser doesn't get what it needs.  There's usually enough information in the line to get a good hint about the underlying problem, so we should look at a representative line or several that represent the same access/problem.

    Cheers - Bob

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