There are a couple of different cases you want to copy files to Azure virtual machines. To copy files to Azure VM, you can use PowerShell Remoting. This works with Windows and Linux virtual machines using Windows PowerShell 5.1 (Windows only) or PowerShell 6 (Windows and Linux). Check out my blog post at the ITOpsTalk.com about copying files from Windows to Linux using PowerShell Remoting.

Prepare your client machine

Prepare the client machine to create PowerShell Remote connections to a specific remote VM.

Set-Item WSMan:localhost\client\trustedhosts -value "AZUREVMIP"

You can also enable remoting to all machines by using an asterisk.

Set-Item WSMan:localhost\client\trustedhosts -value *

Copy Files to Windows Server Azure VM

If you want to copy files to an Azure VM running Windows Server, you have two options. If you are copying files from Windows to Windows, you can use Windows PowerShell Remoting; if you are copying files from Linux or macOS to Windows, you can use the cross-platform PowerShell 6 and PowerShell Remoting over SSH.

Using Windows PowerShell Remoting

To copy files from a Windows machine to a Windows Server running in Azure, you can use Windows PowerShell Remoting.

Prepare the host (Azure VM) to receive Windows PowerShell remote commands. The Enable-PSRemoting cmdlet configures the computer to receive Windows PowerShell remote commands that are sent by using the WS-Management technology.

Enable-PSRemoting -Force

Now you can create a new PowerShell Remoting session to the Azure VM.

$cred = Get-Credential
 
$s = New-PSSession -ComputerName "AZUREVMIPORNAME" -Credential $cred

After the session was successfully created, you can use the copy-item cmdlet with the -toSession parameter.

Copy-Item .\windows.txt C:\ -ToSession $s

Some important notes

• You need to configure the Network Security Group for the Azure VM to allow port 5985 (HTTP) or 5986 (HTTPS)
• You can use PowerShell Remoting over Public Internet or Private connectivity (VPN or Express Route). If you are using the Public Internet, I highly recommend that you use https. I also recommend that you use Just-in-time virtual machine access in Azure Security for public exposed ports.

Using PowerShell Core 6 PowerShell Remoting over SSH

If you are running PowerShell Core 6, you can use PowerShell Remoting over SSH. This gives you a simple connection and cross-platform support. First, you will need to install PowerShell 6. After that, you will need to configure and setup PowerShell SSH Remoting together with OpenSSH. You can follow my blog post to do this here: Setup PowerShell SSH Remoting in PowerShell 6

Now you can create a new PowerShell Remoting session to the Azure VM.

$s = New-PSSession -HostName "AZUREVMIPORNAME" -UserName

After the session was successfully created, you can use the copy-item cmdlet with the -toSession parameter.

Copy-Item .\windows.txt C:\ -ToSession $s

Some important notes

• You need to configure the Network Security Group for the Azure VM to allow port 22 (SSH)
• You can use PowerShell Remoting over Public Internet or Private connectivity (VPN or Express Route). Exposing the SSH port to the public internet maybe is not secure. If you still need to use a public SSH connection, I recommend that you use Just-in-time virtual machine access in Azure Security.

Copy Files to Linux Azure VM

If you want to copy files to a Linux VM running in Azure, you can make use of the cross-platform PowerShell capabilities of PowerShell 6, using PowerShell Remoting over SSH. As for the Windows virtual machines, you will need to install PowerShell 6. Next, you will need to configure and setup PowerShell SSH Remoting together with OpenSSH. You can follow my blog post to do this here: Setup PowerShell SSH Remoting in PowerShell 6

After installing and configuring PowerShell Remoting over SSH, you can create a new PowerShell Remoting session to the Azure VM.

$s = New-PSSession -HostName "AZUREVMIPORNAME" -UserName

After you successfully connected to your Azure VM, you can use the copy-item cmdlet with the -toSession parameter.

Copy-Item .\windows.txt /home/thomas -ToSession $s

I hope this gives you an overview about how you can copy files to Azure VMs using PowerShell Remoting. If you have any questions, let me know in the comments.