This data contains the WinRM payload encapsulated in a SOCKS packet, encryption is dependent on the WinRM/HTTP protocol.The port this runs on is dependent on whatever port the listener was configured with, -D.Unlike a simple Ansible to Windows host over WinRM connection, this scenario has multiple network boundaries that we need to be aware of. Compression of data when running over a high latency networkĪ very basic outline of what this can looks like is.Use SSH keys for authentication, this does not negate the need for WinRM authentication but is used to protect the bastion host.Encryption of data as it goes through the public channel.Channeling the data over SSH gives us a few benefits, such as SSH is fairly ubiquitous in today’s IT environment so I won’t bore you with the details of what is actually happening during this connection. The special sauce in this mix is Secure SHel (SSH) that is used as the channel to transfer the SOCKS data from the Ansible host to the bastion host. The SOCKS protocol does not encrypt or change your data during transit but utilising it with other protocols, like SSH, we can ensure any traffic on a public interface is encrypted. This is unlike a HTTP proxy which forwards the the HTTP request and can include more in depth analysis of the HTTP request itself and act accordingly. It tries to be as transparent as possible and transfers the packet to the client and server unmodified. SOCKS is a proxy that routes traffic back and forth between a client and a server and acts as a middle man between the two. SOCKS stands for SOCKet Secure and the latest standard is SOCKS5 which will be used in this guide. As WinRM is a HTTP protocol we can still use a HTTP proxy to route to our Windows host but this guide is about using SSH through a bastion host so it will ignore HTTP proxies. When we talk about proxies, typically a standard HTTP proxy comes in mind that can forward HTTP requests from a client to another server that the proxy can reach. The main two protocols that are used for this scenario are SOCKS and SSH which are fairly well known and understood so I’ll briefly talk about them. The scope of this post is to not cover the hardening of this host but rather how to configure Ansible to use Windows hosts within an environment like this. Starting in SSH version 7.3 and higher, the ProxyJump command allows us to easily accomplish this.Because a bastion host provides access to an internal network, great care must be taken to harden this host from malicious actors. Many times this is because a machine may be firewalled off from the general internet, but have a connection to a “jump box,” that then allows one to open a connection on the firewalled server. Similar to ForwardAgent, often it is needed to open a secondary SSH connection directly through a a first (or second) target. RELATED: What is SSH Agent Forwarding and How Do You Use It? ProxyJump There is a command, aptly named ForwardAgent, that allows you to “forward” your local keys to the next server in the hop by setting up SSH agent key forwarding. What if you have a scenario where you have opened an SSH connection to a target server, which then needs to make another SSH connection to a second server from that original target server? You might think that you will need to store those same SSH keys on that target server to make this next hop. How do we tell our host configuration to use this file? Host my-ssh-host This tutorial is not going into how to create those, so let’s assume that a set already exists and is properly setup. Instead of a password that can be hacked or guessed, it’s necessary to actually obtain the key file. These are the preferred way to setup an SSH connection. Public/Private KeysĪlmost every SSH tutorial or setup guide out there will usually reference public/private keys at one point or another. The connection will usually prompt for a password, as an SSH connection should not be unprotected. By defining this connection, on the command line we can simply do the following. In fact, you can omit the Port as it’s not strictly necessary because 22 is the default SSH port. Host my-ssh-hostĪs you can tell from the above configuration, this is about as basic as one can get. So, what does a simple SSH connection look like in this file? An example of a simple configuration is below.
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