How to upload Custom Images to Microsoft Azure using PowerShell

In this post, I am going to show how to upload a custom image used in Windows Hyper-V (2016) to Azure cloud. I will be using a combination of the UI in Hyper-V and PowerShell in Azure Resource Manager. I will be working with Azure Resource Manager (ARM) and with Hyper-V 2016 with a custom image of Windows Server 2008 R2 SP1.

Okay, let’s get started.

Prepare On-Premises Virtual Machine Image

First, we need an image to work with. As mentioned, I am using a Windows Server 2008 R2 SP1 (yes, 2008 — needed it for a customer). The VM is Generation 1, which is not only a requirement for Windows 2008, but also a requirement for Azure, as it currently does not support Generation 2 VMs. See HERE to read more on preparing a Windows VHD.

Next, we need to install Hyper-V role on the VM. Since this is a nested VM, we will first need to enable nested-virtualization on the Hyper 2016 box. See a previous post on how to go about this HERE. Once that is complete, go ahead and install the Hyper-V role.

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