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autodiscover.domain.com getting blocked, causing Outlook 365 authentication window to not load properly

So our users aren't currently able to re-authenticate in Outlook if they change their password because the authentication window is popping up blank.

Here's the blocked error I get from the live log:

2019:12:09-15:11:18 utm httpproxy[24965]: id="0002" severity="info" sys="SecureWeb" sub="http" name="web request blocked" action="block" method="CONNECT" srcip="172.20.4.99" dstip="52.97.146.152" user="" group="" ad_domain="" statuscode="500" cached="0" profile="REF_HttProContaExterNetwo (profile)" filteraction="REF_HttCffRdsFilteActio (filter action)" size="150" request="0x9d48a00" url="autodiscover.domain.com/" referer="" error="Connection refused" authtime="0" dnstime="2" aptptime="0" cattime="70" avscantime="0" fullreqtime="2740" device="0" auth="0" ua="" exceptions="ssl" category="105" reputation="neutral" categoryname="Business"

I tried adding the URL to the exceptions list, skipping SSL scanning (and all of the checks actually for testing purposes), but that didn't make a difference.

I then found some similar topics online, with more or less the same issue verbatim, with the suggestion to add a DNS group for autodiscover.domain.com under Misc > Skip Transparent Mode Destination Hosts/Nets. However, this also did not work despite me seeing in three separate topics that this resolved the problem.

Adding the DNS group, I started seeing a new blocked error though:

2019:12:09-15:46:05 utm httpproxy[24965]: id="0002" severity="info" sys="SecureWeb" sub="http" name="web request blocked" action="block" method="POST" srcip="172.20.4.99" dstip="40.100.174.216" user="" group="" ad_domain="" statuscode="502" cached="0" profile="REF_HttProContaExterNetwo (profile)" filteraction="REF_HttCffRdsFilteActio (filter action)" size="2539" request="0xa86fc00" url="autodiscover.domain.com/.../autodiscover.xml" referer="" error="Input/output error" authtime="0" dnstime="3" aptptime="0" cattime="40" avscantime="694" fullreqtime="10363" device="0" auth="0" ua="Microsoft Office/16.0 (Windows NT 10.0; Microsoft Outlook 16.0.11328; Pro)" exceptions="" category="105" reputation="neutral" categoryname="Business" sandbox="-"

Some extra details:

  • The filter profile is in transparent mode, and it's set to "decrypt and scan".
  • The filter action allows all categories with "block spyware infection and communication" turned on and "block websites with a reputation threshold of: suspicious".
  • I make exceptions in the Web Protection > Filtering Options area, rather than using the filter action, because I have multiple filter actions (for other devices) and I find it easier to keep track of everything in the same place. I don't know if there's any real functional difference between the two though, but up until now everything has worked as expected with this approach.

Any ideas?

 

Thanks,

Matt



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