Step by Step Windows Azure Point to Site VPN

There are many scenario in which we have to work on Microsoft Azure Cloud doing experiments
and LABs, or we have to setup some Application Server’s on which different people have to work
like a team, such as a team of developer is working on a project which is hosted on Microsoft
Azure plate from and the developers are located in different geo location. These kind of scenario
for which Azure provides Point to Site VPN Secure connectivity so that every individual connect
remotely with a secure SSTP VPN connection and perform his job.

A Point-to-Site (P2S) configuration lets you create a secure connection from an individual client
computer to a virtual network. P2S is a VPN connection over SSTP (Secure Socket Tunneling
Protocol). Point-to-Site connections are useful when you want to connect to your VNet from a
remote location, such as from home or a conference, or when you only have a few clients that need
to connect to a virtual network. P2S connections do not require a VPN device or a public-facing
IP address. You establish the VPN connection from the client computer. In this Lab, we will walk
through the steps involved in setting up a remote P2S VPN with Microsoft Windows Azure Cloud
plate form.

LAB Setup for Azure VPN

Following is LAB scenario and requirement

We need to following requirements before we start P2S VPN.

• A valid Microsoft Azure subscription
• Microsoft Windows SDK at client computers installed
• Root and Client Certificate at client computers
• Virtual Network in Azure
• Network Subnet
• Virtual Network Gateway in Azure
• Gateway Subnet

Windows Azure Virtual Network

After successful login click New and search Virtual Network

Select Virtual Network, Select Resource Group and Click Create

Virtual Network Properties

Fill out Virtual Network properties as per your Network

Location you can chose as per your nearest Azure Data Center and click create it will take approximate 2 to 3 minutes and V Network will be created.

View Properties of Virtual Network

You can view newly created virtual network settings, resource group and address space.

Creating Azure Virtual Network Gateway

Click on New and in search bar type virtual Network Gateway, it will give you option to create VNG. Virtual Network Gateway will provide you the facility to connect from outside of the world and will act as edge router/firewall at your Azure Network.

Click on VNG
Click on Create when it gives you option for Virtual Network Gateway

On Virtual Network Gateway, you have to provide its, Name, Select Gateway Type, VPN Type, SKU, SKU means Small production workloads on dedicated hardware. Highly available. Capacity is up to 3 replicas and 1 partition (2 GB) it is basically a pricing tier, and Virtual Network selection which we already created.

Choose a Public IP Address

Give a name to your Public IP, it will automatically assign one dynamic public IP address

You can see the full property of the Public IP Address Name


Click OK to create the name of Public IP Address

Click Create, it will take approximately 45 minute to get things done for you.
At this step, we have done Azure part, we will come back to Azure when Gateway creation is finish and we will be done the Certification creation part.

Installation of Windows 10 SDK

As I am using Windows 10 for this Lab, so I have installed Windows 10 SDK (10.0.15063.0), you can install SDK as per your environment. SDK installation steps are simple so I am not adding those in the manual. You can find Windows 10 SDK from below link.

https://developer.microsoft.com/en-us/windows/downloads/windows-10-sdk

Installation of Root Certificate

After successfully installation of Windows 10 SDK, open PowerShell and reach to this path
PS C:\Program Files (x86)\Windows Kits\10\bin\10.0.15063.0\x64>
Once you reach here type cmd

Set path
SET PATH=%PATH%;C:\Program Files (x86)\Windows Kits\10\bin\10.0.15063.0\x64;

Create a directory in C:\temp\Azure and Generate the Root Certificate

Generating Root Certificate

makecert -sky exchange -r -n “CN=MyAzureLabRootCert” -pe -a sha1 -len 2048 -ss My “MyAzureLabRootCert.cer”

View the Certificate in Directory

Generating the Client Certificate

Azure>makecert.exe -n “CN=MyAzureLabClientCert” -pe -sky exchange -m 96 -ss My -in “MyAzureLabRootCert” -is my -a sha1

If succeeded you are good to go.

Exporting Root Certificate From MMC

Now we have to go to Certificate Manage to verify these certificates
• Load MMC, Add the Certificates snap in for my user account.
• Go into personal –> Certificates

Right clikc on MyAzureLabRootCert

Export the Root Certificate

Click Next


Select 2nd option and click next

Click Next

Give a name to your Certificate and click save

Click Next

Click Finish

Click Ok

Export client Certificate

From the same location click Export

Click Next

Select first option and click Next

Click Next

Provide some password

Click Next

Click Ok to Finish
Let’s go the Certification directory in C:\temp\Azure and open the Base64 certificate file in word pad.

Copy the Key only from word pad file.

Connection Making with Certificate Key at Azure

At this point you can go back to Azure port in Virtual Network Gateway  Go to point-to-site Configuration.
Copy this key and paste in Public certificate data area.
Give some name to this Public certificate data
Give the Network Subnet you want that VPN client will get IP from this subnet.

I am using 172.20.20.0/24
You can use as per your network.
Click on Save on top left corner

Notification area will give you progress on saving this.
When its complete it will give, you message of success with green sign

Download VPN Client Option Enabled

As you can see that Download VPN Client option is enabled now, it was disabled before when we were doing its configurations.

Downloading & Installing VPN Client

Select the option which best suits to your operating system. I have Windows 10 x64 so I am going to download x64 client.

Click Save option and run this software

Select Run anyway option to install the vpn client software on the PC.
After successful installation, you can find the Point 2 Site VPN connection in network area

Click on Point-2-Site-VPN-VNet

Click on Connect

Windows Azure Virtual Network Status

You will see Windows Azure Virtual Network Click on Connect

On elevated privilege screen click on continue

You can see the connection is verifying the password & other settings.

Now the connection is established with Azure Virtual Network Gateway

Creating a Virtual Machine in VNet at Azure

You can further create a VM Linux of Windows in Azure under your above created Network, I have built an Ubuntu VM

As you can see an IP address from my VNet is assigned to this Ubuntu VM, you can do two thing to verify, one you can ping this IP from you connect client machine VPN CMD, second you can establish SSH connection to this VM and can see the stats on the Azure portal under Gateway  Point to Site Configuration.

You can see the continues ping status to Azure VM from VPN client machine.

P2S VPN Connection Status

When you will start accessing this VPN resources, you can also monitor the traffic statistics at Azure Portal.

I hope this will help you out 😊

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