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Outlook Office 365 not prompting for user credentials when first sitting up on virtual machine

Posted on 2016-07-27
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Last Modified: 2016-08-01
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?
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Question by:jhyiesla
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by:jhyiesla
ID: 41731687
Some additional info.  On my computer, not a VDI, I am OK to run and configure Outlook.  However, logged on with one of our newly migrated test users who's never been on the machine before and am getting same error.  We've also found that on VDI, if we have user who's worked in the past and we remove the persona management profile, we get the same error and the wizard will not complete.
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Expert Comment

by:Jackie Man
ID: 41732268
Run remote connectivity analyser in your virtual desktop and post back the result.

https://testconnectivity.microsoft.com/
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Author Comment

by:jhyiesla
ID: 41732916
Specifically which test(s) do you want me to run; there are a ton of them.
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Expert Comment

by:Jackie Man
ID: 41732919
All of them.
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by:jhyiesla
ID: 41732997
I ran several of the test, but was getting a common theme so stopped. It all seems to have to do with Autodiscover. It seems that any attempt to use autodiscover fails.

But when I added in WireShark I can get the user to work, but when I ran a couple of the tests again, I still got the autodiscover error. And I still think that the WS thing may be a fluke, because it's installed on my computer and everything works for me, but not for a new user that I signed on with.
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Expert Comment

by:Jackie Man
ID: 41733025
Actually, your current setup of using Exchange online in virtual desktop environment is not a supported solution which will lead to nightmare in the long ru~.

Unless you have acquired solution like profile container, it is not recommended to proceed with the deployment.

http://www.edunnewijk.nl/fatshark/index.php?/categories/2-Work/P3.html
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by:jhyiesla
ID: 41733058
An interesting article.  

I ran that same test on my computer and got the same thing...failure of autodiscover.  However, on my computer my O365 account is working fine with Outlook, but if I sign on with another user it fails. Of course I already had an established account on my computer for me.  Also, I have a Mac and in Mac Mail I was able to set it up just fine and it works on my phone, but that's an outside connection.

When the wizard fails, I also have tried setting it up manually putting in the server name of the Exchange server, the Hybrid server and the O365 URL... these also fail.

I also just tried one of the test users on a VDI desktop and it looked like it was going to work as I got the credential prompt. The roaming profile only applies to virtual desktops so it's not like it was triggered by a successful setup on a real computer.  Then I deleted the roaming profile and tried again on a new desktop and it failed.
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Jeffrey Kane - TechSoEasy earned 500 total points
ID: 41735338
All of them.

That's gotta be the most ridiculous advice I've ever heard.  C'mon Jackie if you don't know about something please don't cause people to run in circles.

The only test you need to run there is under "Microsoft Office Outlook Connectivity Tests" -- the Outlook Autodiscover test.  Please do run that.

Then, let's be clear, Office Pro Plus is absolutely supported in a VDI environment:
https://blogs.technet.microsoft.com/uspartner_ts2team/2013/08/31/clarification-of-office-365-pro-plus-support-in-vdi-environments/

BUT -- you need to be sure you've installed Office properly -- otherwise you will run into activation issues.

This is a pretty good how-to for that:
http://svenhuisman.com/2015/02/how-to-configure-office-365-pro-in-a-non-persistent-vdi-environment/
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Author Closing Comment

by:jhyiesla
ID: 41737816
We actually figured it out. and Techsoeasy's suggestions were more to the point than anything else.

The actual solution that we stumbled upon was from running the test email connectivity from within Outlook. It pointed to an issue with connecting to the onmicrosoft.com site. We played around with some DNS changes and a CNAME setting, which worked, but which prompted us for a certificate bypass each time we started Outlook. Ultimately, it came down to onmicrosoft.com not being allowed through our web filtering software. I had put a bunch of those in the filter from a list we got from our consultant, but either I missed this one or it wasn't on the list or I had it too tightly defined. Anyway, once I added onmicrosoft.com to the filter, Outlook started working just fine on VDI units with cloud-based emails.
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