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Is it possible to deploy from Azure DevOps to an Azure VM that only has a private IP address? I need to deploy to VM's that won't always have a public IP address.

I thought there might have been some internal Azure network that could be used but running the deployment agent script on my VM without a public IP fails (it works if the machine does have a public IP). Other than that can Azure DevOps connect to a Azure VPN (Virtual Network Gateway) to access the VM's on my Virtual Network?

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Yes, it is possible. You can use Self-Hosted agents directly on one or all of the VMs: Link

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