SSH Proxy Jump Host on Windows


Windows Connectivity

Listed below are common examples of how to utilize the SSH Proxy Jump Host on the Windows OS platform.  Additional questions or concerns not answered by this article may be directed to the Help Desk

 

PowerShell / Command Prompt / Terminal:

From the PowerShell, Command prompt, or Terminal type in the following command:

ssh -J bluekey_username@sshjump.depaul.edu remote_server_username@target_server

Use your BlueKey password when prompted for the “Entra Id Password” below.

 

 

You will need to use your MFA method and enter the number as shown below.

 

 

You will now be proxied to the destination server and can use SSH as normal.

 

 

PuTTY

 

You will need to configure your server connection and tell it to use a proxy.  The server session configuration is as normal.

 

 

After setting the Host Name for your session, you will need to click on Proxy which is under Connection.  You will need to select the Proxy type “SSH to proxy and use port forward” and enter in the Proxy hostname “sshjump.depaul.edu”.

 

 

Usage is just like using command line SSH, you will need to enter your BlueKey password when prompted for the “Entra Id Password” below.

 

 

You will then need to use your MFA method and enter the number as shown below.

 

You will then be connected to the server.

 

WinSCP for File Transfers

The WinSCP client supports using a Jump Server with MFA.  You will first need to set up a new Site. The Site Manager window should open when WinSCP opens (if it does not, go to Tabs > Sites > Site Manager). In the window, you will set up a New Site. Fill the fields with the following information, which you may have received from your professor (for class) or from an IS staff member (for deployed servers you administer):

Leave the Password field blank. You will be prompted for this when connecting.

 

Click on the Advanced button, then click on Tunnel under Connection on the left. In the main window, enter the following: 

Click OK. You will be returned to the screen in step 1. Click Save under the User name field. In the window that comes up, set the name you wish and click OK to save the new name and configuration. 


You are now ready to login to the server. Click the Login button to begin connecting.

You may be shown an authentication banner like the above. Click Continue after reviewing the policy.  

When the software tells you you will need to enter your password, press OK.

When the prompt comes up for your Entra Id (BlueKey) password, enter that password and click OK. 

You will then be provided with a number to pass to your MFA, enter that in your MFA then click OK to continue:

After this, you may see one or all of the following: 

  • A prompt about accepting a fingerprint to add to login to the server. Click OK or Yes to accept this (this should only appear once, if it does at all).
  • A second authentication banner. Click OK as before.
  • A second prompt for your BlueKey password. Enter it as before when you are prompted. 

 

If authentication is successful, you will see your local files on the left, and be passed to your home directory on the target server (displayed on the right).

Navigate through your files and folders on the left until you find what you wish to upload. Either click on them and drag them to the right pane, or hold down CTRL and click on all files you wish to upload, right-click them and choose Upload to do so.