I created a Server 2008R2 VM in Hyper V, ran Sysprep on it, then uploaded the VHD to Azure via Azcopy.

Then I converted the VHD file into a managed disk, and created a VM from the managed disk.

Now I am unable to RDP to this VM to complete the installation.

I tried running mstsc /admin however this didn't work either.

I installed boot diagnostics and got a picture of the current state, however I'm not sure how to proceed from here.

Is there any way I can connect to it to complete the installation?

screenshot of current VM state (via boot diagnostics)


  • 1
    Can you RDP to the original VM you created in Hyper-V? If not, boot it in audit mode, fix it and try again. – Michael Hampton Nov 9 '18 at 3:27
  • Hi Michael, can you elaborate on your solution? What does booting into audit mode do? – Jon Nov 9 '18 at 3:51
  • Audit mode lets you make changes to a sysprepped system without going through OOBE, as if you hadn't sealed it. You can then reseal it again. Press Ctrl-Shift-F3 at the OOBE screen shown in your screenshot to enter audit mode. – Michael Hampton Nov 9 '18 at 3:54

You must have missed the step in the process to convert VHD to and Azure Image before deploying. Below is a link to the process.


At this point you will have to delete VM and disk. Upload sysprep VHD again, this time convert to image then deploy from image.

Easiest and fastest way to fix issue.

  • This is true, I missed that step, I actually took the VHD and converted it to a managed disk, and then an imjage, – Jon Nov 9 '18 at 6:49
  • However I attempted the steps as per the article, created an image from the generalized VHD, and then and created a VM from the image, which still had a similar problem (wouldn't boot up) ... as per this img imgur.com/tkvpR2C – Jon Nov 9 '18 at 6:50
  • actually, the VM resolved itself automatically (after a while) and now I can log on. (Following the steps mentioned above in that article) – Jon Nov 9 '18 at 7:12
  • Don't forget to mark question as answered. – Hannel Nov 14 '18 at 6:45

There's no RDP functionality during the specialize phase of Windows Setup, which is the phase you're seeing in your screenshot upon first boot of your sysprepped VM. You're going to need to use Sysprep with an answer file so that the specialize phase runs unattended.

There's no traditional "console" access to an Azure VM. There's a serial console connection available, but I don't believe you can use it to configure the VM while it's in the specialize phase of Windows Setup.


Your Answer

By clicking "Post Your Answer", you acknowledge that you have read our updated terms of service, privacy policy and cookie policy, and that your continued use of the website is subject to these policies.

Not the answer you're looking for? Browse other questions tagged or ask your own question.