This discussion has been locked.
You can no longer post new replies to this discussion. If you have a question you can start a new discussion

Office 365 Certificate errors - Suppliers blaming my web filtering

I haven't been at this company long and I've never managed a Sophos UTM before but every user here is plagued by certificate errors in Outlook.

We use Office 365 and Outlook 2016  and users are constantly presented with this prompt...

Of course many users click No and then their email doesn't work...

it's pretty obvious what's wrong there, the certificate should be issued to "autodiscover.company.co.uk" but it is showing as issued to "autodiscover.company.co.uk.company.local"

I spent a while complaining to the people who supply our Office 365 contract but they concluded...

"Do you have a firewall in place that filters or monitors web traffic? It looks like there is a device that is intercepting the https requests which is why we are seeing the certificate alerts (autodiscover.company.co.uk.company.local – something is intercepting the request and appending .company.local)"

I have seen related and similar threads on the forum but nothing that seems to quite fit. I checked our exceptions and we have this relevant looking one setup

Can anyone suggest what else I should look for?



This thread was automatically locked due to age.
  • Looks like your webfilter is scanning and decrypting HTTPS traffic. Fastest solution is to stop decrypting HTTPS traffic, then you'll get the certificate that is presented by the remote webserver and not the one that is presented by your webfilter (proxy).

    If you do need to decrypt https traffic, then you might need to configure exceptions for your autodiscover.company url.


    Managing several Sophos firewalls both at work and at some home locations, dedicated to continuously improve IT-security and feeling well helping others with their IT-security challenges.

  • Hi, Chris, and welcome to the UTM Community!

    Did you resolve this?  Do you see unwanted activity in the Web Filtering log related to O365?

    Cheers - Bob

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