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

Exchange server with 'Windows Extended Protection' behind WAF

Hey, I was wondering if anyone who has their Exchange server(s) behind a Sophos UTM WAF (to publish OWA, Autodiscover and Outlook Anywhere) has activated 'Windows Extended Protection' yet and if there were any problems or not.


This thread was automatically locked due to age.
  • We are going to test this the coming week. I will report back, then.

    Mit freundlichem Gruß, best regards from Germany,

    Philipp Rusch

    New Vision GmbH, Germany
    Sophos Silver-Partner

    If a post solves your question please use the 'Verify Answer' button.

  • Do a Google on OWA Autodiscover Outlook Anywhere waf and you'll get many tips.  Einige auf Deutsch.

    Cheers - Bob

    Sophos UTM Community Moderator
    Sophos Certified Architect - UTM
    Sophos Certified Engineer - XG
    Gold Solution Partner since 2005
    MediaSoft, Inc. USA
  • We activated the Extended Protection yesterday on all Exchange servers and since then, Outlook Anywhere stopped working.

    Everything from inside the company works fine, also Smartphones are able to sync mails but Outlook from external connections is not working. So we are doing a rollback.

    For a short test we disabled the Webserver Protection and did a 80 and 443 NAT to the Exchange Server and it worked. After enabling the Webserver Protection it Outlook Anywhere stopped working again.

    At the Exchange Server Eventlog we see:

    An account failed to log on.
    Security ID: NULL SID
    Account Name: -
    Account Domain: -
    Logon ID: 0x0
    Logon Type: 3
    Account For Which Logon Failed:
    Security ID: NULL SID
    Account Name: (edited)
    Account Domain:
    Failure Information:
    Failure Reason: An Error occured during Logon.
    Status: 0xC000035B
    Sub Status: 0x0
    Process Information:
    Caller Process ID: 0x0
    Caller Process Name: -
    Network Information:
    Workstation Name: edited
    Source Network Address: edited
    Source Port: 34080
    Detailed Authentication Information:
    Logon Process:
    Authentication Package: NTLM
    Transited Services: -
    Package Name (NTLM only): -
    Key Length: 0

    So we disabled the Extended Protection and everything works through the Webserver Protection again.

    Is anyone able to use the Extended Protection together with Exchange Webserver Protection through UTM?

  • I just got the following feedback from MS:

    based on my understanding, the Sophos UTM Webserver Protection intercepts the HTTPS connection ( and so, is considered as a Man-in-the-Middle (MitM) and this is a scenario that Windows Extended Protection actively tries to prevent. Therefore, you see the credential prompts as the server doesn't accept the connection.
    If the UTM uses SSL Bridging (Client --HTTPS-- UTM --HTTPS-- Exchange), it's required to use the same certificate on the device between the client and the server (in your case, the UTM). If you perform SSL Offloading (Client --HTTPS-- UTM --HTTP-- Exchange) this isn't supported and will not work together with Extended Protection turned on as we need the certificate for the Channel Binding Token (CBT).
    For more information see:

    That means the automated LetsEncrypt (on tool at the UTM and one at the EX Server) is dead?!

  • Same Problem here(UTM). After Update Exchange and enabling EP anything works fine except Outlook from external connections. We disable the extended Protection and open  a ticket to solve the Problem. Seems like the XG works.

  • As stated in my post below: There is nothing a ticket could solve, because one of the features of EP is eleminating any man-in-the-middle attacks. That means you have to use the exact same certificate at the Exchange and the UTM Webserver Filter. No more Lets Encrypt... We have to buy certs again, that last some years.

  • Do you request the LE certificate on both the UTM and Exchange seperately or why is it not the exact same certificate?

  • Yes of course, there is no way (that I know) to export/import the LE-Cert at the UTM or Exchange and import it on the other device automatically / without manual interaction all 2-3 months.

  • The certificate can be imported from the UTM via a PowerShell script on the Exchange server. That is what we do. Here's a guide (in German):