OpenSSH Resources for Windows and PowerShell

Had a conversation with a good friend in the SQL Community about OpenSSH and how it fits as a transport layer for PowerShell Remoting. I pointed him towards several resources I have online. So here’s a post aggregating those resources.

If you’re looking to get started with OpenSSH on Linux and Windows Systems check out thisPowerShell Summit presentation I did in 2018. This covers OpenSSH in theory and practice.

Session: OpenSSH Internals for PowerShell Pros

  • Remote Access Concepts
  • OpenSSH Architecture
  • Authentication Methods (including Key Based Authentication)
  • OpenSSH Server and Client Configuration

If you’re looking to get started with OpenSSH based PowerShell Remoting check out this session from PowerShell Summit in 2018 co-presented with Richard Siddaway.

Session: PowerShell Remoting: Installing and TroubleShooting in a Multiplatform Environment

  • Installing OpenSSH on Windows and Linux
  • Authentication Users (Including AD Authentication)
  • Setting Up PowerShell Remoting on Windows and Linux
  • Troubleshooting OpenSSH

Shortly after I did the sessions above, OpenSSH was released as a Window Capability, check out this blog post on how to install OpenSSH at the command line using Add-WindowsCapability.  This also applies to Windows 2016 Server. 

Session: Firewall Evasion and Remote Access with OpenSSH

  • OpenSSH is much more than just remote terminal access to servers, it provides a full suite of remote connectivity methods to your network and its services. In this session, we will look at how to use OpenSSH and its forwarding, tunneling and VPN capabilities so that we can reach securely reach network services that are behind firewalls and other security boundaries. Common use cases for these techniques are cloud jump boxes, secure access into segmented networks and being able to get remote access and move data around in poorly secured networks….these tips are things that will likely get you some extra attention from your security team

Blog Post: Configuring Passwordless PowerShell Remoting over SSH

Blog Post: Distributing SSH User Keys via PowerShell

Blog Post: Installing OpenSSH Server on Windows 10

Blog Post: PowerShell Remoting in Multi-Platform Environments using OpenSSH