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WebFilter and https://outlook.office.com or https://outlook.office365.com "Host not found" HELP

Okay, so I have setup the Web Filtering and using the transparent mode. I have added exceptions for Office 365 as we're using Microsoft Office 365 for SharePoint and Exchange. Which all has been working well and I cannot tell by the error what is occurring here when the Outlook Web Access (OWA) is reporting invalid HTTPS cert (from the UTM) as well the error reads Host not found.

UTM Error Page:

While trying to retrieve the URL:
The content could not be delivered due to the following condition:
Host not found
Your cache administrator is:
MyEmail@apexanalog.com
Testing done:
I have reviewed  the web filter live log (if you would like to see) which shows status codes 200, 502 then final of 304.
The Base Policy is one that states blocks when testing https://outlook.office.com/owa the exception is listed. The Reason is Host not found. So, I am really lost with this error reason. https://outlook.office365.com/owa works with the Policy HelpDesk. Is this a DNS issue cause testing this in browser it varies from outlook.office.com to outlook.office365.com.
I cannot figure out where this is getting hung up. I have web filter options to allow many Office 365 items. This is the only one complaining. The SSL warning before reaching the page is from Astaro the UTM, and I did not think I would get such since I am using transparent mode web filtering.
Please let me know what I can look at, at this point I am drawing a blank. There is no reason I see as to why this should be occurring.
Any assistance would be greatly appreciated. Thanks in advance!


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Parents
  • Nudge, nudge.

    Anyone able to assist? Need more information on where I can locate why the failure of Office 365 Professional OWA page? The certificate errors and is published by Astaro, so know the certificate is from UTM, then users (self included) get UTM Web Filtering error "host not found". I'm not able to track down a solution since I think UTM is processing more than just web-filter here.
    Waiting and need assistance soon.
Reply
  • Nudge, nudge.

    Anyone able to assist? Need more information on where I can locate why the failure of Office 365 Professional OWA page? The certificate errors and is published by Astaro, so know the certificate is from UTM, then users (self included) get UTM Web Filtering error "host not found". I'm not able to track down a solution since I think UTM is processing more than just web-filter here.
    Waiting and need assistance soon.
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