We use VMware to build our images, and then we sysprep them and upload them to the k2000. However, we put Microsoft Office 2010 on our image to speed the post-image process along. I'm not sure why, but whenever we open Outlook after deploying an image, we get the "upgrade in progress" error, where we are told we have to "upgrade outlook connector". We've been just doing a repair of office and moving on, but I'd like to get it sorted out as to why this is happening. The image is fine before we upload it and deploy it.
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I know this is an old question, but maybe this will help someone in the future.

The problem (which I also encountered in Office 2016) appears to be related to NTFS short names being disabled when manually partitioning a drive during setup in recent versions of Windows (8 and newer) and WinPE (4 and newer). When short names are explicitly enabled by formatting the primary partition with /S:ENABLE´╗┐, the problem should go away.

I say should, because the Systems Deployment Appliance (in 5.0.222 at least) has this flag set in the "Format C: as NTFS" pre-installation task, but I was only able to get the problem solved by formatting C: with that flag during the initial setup of an image, not during deployment. I was also able to get pre-existing images working by capturing them as WIMs instead of K-Images.

Source: https://social.technet.microsoft.com/Forums/ie/en-US/1c7595a5-8a16-4bd4-9d92-9cdbf011147a/outlook-2010-and-imaging?forum=officesetupdeployprevious

Answered 12/12/2017 by: clpo13
White Belt

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How are you installing Office?

You should be using the office customization tool (setup.exe /admin) to create an msp and then install Office using that file (setup.exe /adminfile "file")

We install Office on our image using this method and never had a problem.
Answered 12/16/2015 by: h2opolo25
Red Belt

  • We've been running just the normal setup.exe - how should I be configuring it differently?
    • http://www.itninja.com/blog/view/configure-a-silent-installation-of-office-2010
  • I configured and installed office with a .msp file, but the issue is still happening. Something between sysprep, the upload to the k2000, or the download to the computer is causing office to break somehow. We have "copy profile" chosen in the answer file as well, I know some people stated that could be an issue.
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