Using Cloud Middleman on Windows

How to install our root CA, install the device certificate, and connect to Cloud Middleman's VPN server

Windows configuration can be divided into 3 steps:

Install the CA certificate. This is required for Windows to trust the SSL certificates that we issue. You'll only have to do this once per device.
Install the Client Auth chain. Windows requires that VPN client authentication certificates have a fully-qualified chain, so you'll need to install this.
Install the Device Certificate. The VPN connection uses machine certificate authentication, so you'll need a certificate installed.
Configure the VPN. In order to log traffic, Cloud Middleman requires a connection to our VPN server.

(These directions target Windows 10 specifically, but users of Windows 7 and up should be able to follow along as well.)

Install the CA Certificate

Cloud Middleman requires you to install a CA certificate to allow us to intercept your https traffic. If your device has a limited domain whitelist configured, we will generate a special CA that is valid for only these domains; otherwise, we'll provide you with a link to our global CA certificate.

Step 1: Download the provided CA Certificate. It should have a .crt extension.

Step 2: Open the file from windows explorer (or from your browser). You should see a dialog like the following. Click the "Install Certificate" button.

Step 3: Import the certificate into the Local Machine store, as in the screenshot below:

Step 4: Make sure to install the CA certificate into your "Trusted Root Certification Authorities" store.

You have now installed our CA certificate.

Install the Client Auth Certificate Chain

Step 1: From the device invitation screen, download the Cloud Middleman VPN Certificate bundle.

Step 2: Open the certificate file (file extension .p12 ). Windows should present you with a certificate installation wizard. Choose Local Machine as the destination store.

Step 3: Follow the directions of the wizard, leaving the certificate password field blank when prompted. Leave all other settings as their defaults and complete the wizard.

Install the Device Certificate

Step 1: From the device invitation screen, download your device certificate by clicking the button. This is also a good time to copy the password.

Step 2: Open the certificate file (file extension .p12) . Windows should present you with a certificate installation wizard. Again, choose Local Machine as the destination store (it will not be found by the VPN configuration otherwise).

Step 3: Follow the directions of the wizard, entering the certificate password when prompted. Leave all other settings as their defaults and complete the wizard.

Configure the VPN

Step 1: Navigate to the Network and Sharing Center. The easiest way to do this is to search for it from the start menu:

Step 2: Click on "Set up a new connection or network".

Step 3: Select "Connect to a workplace" and click Next.

Step 4: Select "Use my Internet connection (VPN)" and click Next

Step 5: Enter cloudmiddleman.com as the Internet address. You can use whatever you like as the destination name. Click Next.

Step 6: Back at the Network and Sharing Center, click on "Change adapter settings" in the left menu.

Step 7: Right-click on your newly-created VPN Connection and choose "Properties".

Step 8: Under the "Security" tab, make the following changes:

Choose "IKEv2" as the VPN type
Choose "Require encryption (disconnect if server declines)" from the Data Encryption dropdown
Choose "Use machine certificates" as the Authentication method

You should now be able to connect to the VPN. Make sure you remember to confirm your connectionhttp://cloudmiddleman.com/docs/completing-your-vpn-connection! If an error occurs, double-check the above steps, then proceed to the Troubleshooting Guide.