Outlook Office 365 not prompting for user credentials when first sitting up on virtual machine
Posted on 2016-07-27
We're moving to Office 365. Almost all of our desktops are virtual desktops running VMware View. Here's my issue.
If I set up Outlook for a user whose mailbox has been moved to the cloud on a regular computer it works just fine. If I attempt to do that on a virtual desktop when the wizard gets to the point where it's trying to connect to the server and should prompt the user for credentials, it does not, causing the wizard to fail.
Initially I thought it might have something to do with the fact that the virtual desktops are on a different LAN segment, but I can ping everything back and forth so I doubted that was the issue.
On a whim, I decided to install Wireshark on an IT pool that I have set up to see if it would illuminate the problem. Much to my surprise, I was able to install Outlook just fine. But that was puzzling since there's no infrastructure difference between a standard virtual desktop and the IT one.
Long story short, I discovered that when I install WireShark, the Outlook wizard works just fine, prompting the user for credentials and finishing the Outlook wizard. I've looked at the installed programs before and after installing WS and other than the install of winPCAP and WS itself the only other change I saw was a different version of some C++ redistributable, but I checked my machine, on which Outlook works OK and I don't have that version installed, so I doubt that's it. I checked the running services before and after the install and nothing is different their either, except Windows updates is running after the install. I tried manually just starting that program and the Outlook wizard still failed.
WS is dumping a bunch of DLL files into place and I have done the suggested optimization on the master before building the pool. Obviously something that the WS install is doing is allowing the Outlook wizard to complete. Anyone have any idea what that might be?