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Azure Files - Point-to-Site VPN Tunnel


Azure Files offers fully managed file shares in the cloud that are accessible via the industry standard Server Message Block (SMB) protocol.

Azure file shares can be mounted concurrently by cloud or on-premises deployments of Windows, Linux, and macOS.

While connecting from on-prem, sometimes ISPs block port 445.Azure VPN Gateway connects your on-premises networks to Azure through Point-to-Site VPNs in a similar way that you set up and connect to a remote branch office. The connectivity is secure and uses the industry-standard protocols KIEv2.

With this tutorial, one will be able to work around port 445 block by sending SMB traffic from a Windows machine over a secure tunnel instead of on internet.

This is a custom deployment for Azure Files of Point to Site VPN solution. In order for Point to Site VPN to work well Azure Files, Storage service endpoint should be added to virtual network. The template below takes care of these configuration settings.


General instructions is available at Point to Site Setup in Portal doc. The instructions below are specific to Azure Files Point to Site VPN interop.


  • You have a valid Subscription with admin permissions
  • A storage account
  • An Azure File Share
  • A Windows machine on which you would like to mount Azure file share

Step 1 - Generate Root and Client Certificate

The steps below helps you create a Self-Signed certificate. If you're using an enterprise solution, you can use your existing certificate chain. Acquire the .cer file for the root certificate that you want to use. To learn more about certificates and Azure VPN interop read the Azure Point To Site VPN documentation.

  • Run the generatecert.ps1 powershell script as Admin. Update the variables to the desired values. Especially the ones highlighted in screenshot below.

    how to generate certs

  • From the output console, copy the certificate signature from output window (the highlighted portion in screenshot below).The Certificate Signature will be an input to the ARM template. DO NOT copy ---- BEGIN CERTIFICATE --- and ----- END CERTIFICATE -----. Only copy the text in between.

    Generate Cert Output

This powershell script will generate self-signed root and client certificates and also export the root certificate signature and client certificate file. Client certificate is automatically installed on the computer that you used to generate it. If you want to install a client certificate on another client computer, the exported .pfx file is also generated in the script which will be stored on local drive.

Certificates are used by Azure to authenticate clients connecting to a VNet over a Point-to-Site VPN connection. Once you obtain a root certificate, you upload the public key information to Azure. The root certificate is then considered 'trusted' by Azure for connection over P2S to the virtual network. You also generate client certificates from the trusted root certificate, and then install them on each client computer. The client certificate is used to authenticate the client when it initiates a connection to the VNet.


In case you are using an enterprise root certificate, modify the script accordingly and execute.


Client cert needs to be installed on every connecting client. You can either install the same client cert (after it is created and exported as done in the script above) or create one for each client using root cert.

Step 2 - Find your Storage Account IP

You will need custom routes IP address range to be fed into the ARM template that will be run.

Get the Storage account IP. Get this by running nslookup. Make sure you replace StorageAccountName with your own storage account's name.

nsloopup <StorageAccountName>

Output will be something like


Step 3 - Deploy ARM Template to create VNet and P2S VPN Gateway

  • Click Deploy To Azure button above. It will take you to Azure Portal.

  • Paste the Client Root Cert Data copied from first step.

  • Paste the Storage Account CIDR Address in VPN Client Custom Routes copied from from step # 2. Note this has to be in CIDR format. For example if the output of Step #2 is, then one needs to pass value as [""] as field expected CIDR format and not ip address.

  • Fill other necessary info and click Purchase.

  • This deployment takes ~30-45 minutes to complete.

    Run ARM Template

This template creates a VNet with a Gateway subnet associated to Azure Storage Service endpoint. It then creates a public IP which is used to create a VPN Gateway in the VNet. Finally it configures a Dynamic Routing gateway with Point-to-Site configuration including VPN client address pool, client root certificates and revoked certificates and then creates the Gateway.

Step 4 - Download and install the VPN client

  • Once the deployment fully completes, click on your gateway and go to the Virtual Network Gateway >> Point-to-Site confirmation tab from the left pane. Download VPN client by clicking the button on the top.

    download VPN client

  • Unzip the client and browse into the folder.

  • If you are running amd64 - Run VpnClientSetupAmd64.exe from the VPN Download client that was just installed WindowsAmd64 folder, run the x86 version in case your client is x86.

    Install VPN Client

  • Start the VPN client.

Step 5 - Install Client cert [Optional Step]

This step is only needed if you are installing VPN on a different computer than where certificates were generated using generatecert.ps1 in step # 1 above. If you are using the same machine, the client cert was already installed as part of step #1.

These instructions are assuming that you generated the client cert and exported it when generatecert.ps1 was run.

  • Locate the cert on your machine that was exported and double click on P2SClientCert.pfx. This will be at the path that you specified for variable $pathtostoreoutputfiles.

    Located exported client cert

  • Follow the prompt and when prompted for password, input the value you had provided to variable $clientcertpassword to script. Install cert first 3 steps

  • Follow the prompt and use default values until it says that certificate is successfully installed.

    Install cert last 4 steps

Step 6 - Persist and mount Azure File Share

Persist your Azure Files credentials and use a persistent mount to enable mounting at every startup after reboot.

Here are the details instructions to persist connection for Azure Files. At a high level follow the instructions below -

  • Persist credentials using following command

    cmdkey /add:<your-storage-account-name> /user:AZURE\<your-storage-account-name> /pass:<your-storage-account-key>
  • View the persisted credentials. There should be an entry with your Storage Account name.

    cmdkey /list
  • Mount the file share using -Persist and with no credentials provided. The example below shows mapping to X drive, but you can mount to any drive letter.

    New-PSDrive -Name X -PSProvider FileSystem -Root "\\<your-storage-account-name>\<your-file-share-name>" -Persist 

Step 7 - Add additional storage accounts [Optional Step]

Update the custom routes on existing Gateway and then redownload VpnClient package. Note currently Powershell is available. Portal and CLI support are coming soon.


Thats it. This will get you to a Point to Site VPN setup that works well with Azure Files. In case of questions, please contact

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