Case of the Office 365 “Something Went Wrong”

Intermittently in SharePoint Online the Office 365 toolbar would just not appear. In other cases it would appear but Outlook Web Access would get stuck at logon and eventually fail with message “something went wrong” 


This problem only occurred to users on the corporate network, and was not affecting users connecting to the sites externally.

Looking at a WireShark capture we could see traffic was going “direct” instead of via proxy.

We were also able to reproduce the issue while running Fiddler

With Fiddler we were able to identify easily:


In the details view fiddler provided this information:


Looking up these IP addresses we could find they were part of the Akamai content delivery network, used by Microsoft.

Server:  UnKnown



Checking proxy configuration we noticed a PAC file in use. We tested with proxy set manually to server and port number and the site worked. So we needed to check the PAC file. At first glance it appeared the PAC file should have resolved these URLs to Proxy

/* Externally hosted sites to be proxied */

if (dnsDomainIs(host, “”

|| dnsDomainIs(host, “”))
    return ProxyChoice(MyIP,host);

The problem here is don’t assume the comment “to be proxied” actually means they are going to be proxied. As we can see it is returning the value of a function ProxyChoice.

Using my PacDbg tool here I was able to quickly figure out why it was going direct…

We can see within ProxyChoice function there was a statement that would return DIRECT


These statements had been added in to improve performance of heavy utilized site by bypassing the proxy.

Why did it work most of the time going DIRECT?

This is because the firewall had rules to let out HTTP/S traffic to documented Office 365 IP addresses

However the host names and are load balanced sites that are constantly returning different IP addresses. Whenever there was a failure it was because the IP address was not permitted “direct” due to firewall rules. 

Adding the new IPs to Firewall fixed the issue, but this risked breaking again when new IPs were introduced, so the PAC file was modified to ensure these went via proxy.

About chentiangemalc

specializes in end-user computing technologies. disclaimer 1) use at your own risk. test any solution in your environment. if you do not understand the impact/consequences of what you're doing please stop, and ask advice from somebody who does. 2) views are my own at the time of posting and do not necessarily represent my current view or the view of my employer and family members/relatives. 3) over the years Microsoft/Citrix/VMWare have given me a few free shirts, pens, paper notebooks/etc. despite these gifts i will try to remain unbiased.
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