Hi all,

We're currently testing the roll-out of Office 365 ProPlus with shared computer activation but are having problems with Office automatically activating (with no user prompts) when using our web proxy.

I've already added proxy exceptions (in our PAC file) for the 'Office 365 portal and identity' and 'Office 365 ProPlus' URLs (not Content Delivery Network) from https://technet.microsoft.com/en-us/library/hh373144.aspx but test licensed Office 365 E4 users still get the 'Activate Office' prompt and even if they enter in their credentials are ultimately told 'There is a problem with your account. Please try again later'.

Testing this on a computer not directed through the web proxy works fine and users get no pop-ups whatsoever and Office is licensed.

The problem is I can check the traffic passing through the proxy in real-time and no traffic destined for any of the URLs on the TechNet page actually goes out over the proxy, indeed there is no Microsoft orientated traffic at all. It's as if simply specifying a proxy on IE's connection settings breaks shared computer activation.

I'm in the process of a support case with our web proxy company itself but if there's anyone out there who can shed any light on this it'd be appreciated.

Thanks in advance.

I have just tested this with a completely different web proxy service and get the same behaviour, thus this appears not to be a specific web proxy issue but rather an "Office 365 ProPlus working with proxies" issue.

Read this: https://technet.microsoft.com/en-us/library/gg702620.aspx

Next read this: http://blogs.technet.com/b/neiljohn/archive/2012/01/26/office-365-proxy-server-exclusion-list-office-365-service-url-s.aspx

Last: My workaround that's about 6 months old:I went through the same issue with Websense Cloud Web Security Gateway in my RDSH environment.

Off and on, and seemingly without provocation, users would be prompted for credentials and these credentials would sometimes be accepted and other times they could just cancel out and continue working.

I chalked this up to Microsoft's continual tuning and scaling of their cloud environment (we use Office 365).  I suspect Websense was not able to add hosts fast enough and the authentication issue just popped up from time to time.

My solution? A workaround...set the list of recommended MS servers on "bypass" so that any traffic destined to these servers Websense would essentially permit without interference.

Best of luck to you.

Thanks SnCln.  I did exclude a heap of URLs and locations from our proxy but never got past the issue.  Microsoft PSS helped out as far as they could but put it down to the way our proxy performed authentication (we use SSO).

Luckily we were at the end of our web filter contract and so have now migrated to a new one; Blue Coat ThreatPulse, whose VPN-based routing method works great with Office 365's activation technologies.