Setting up Windows hosts for Ansible control using OpenSSH

Microsoft has made great strides in supporting and embracing the open source community, and has added a number of popular open source packages to their OSes. One of the most notable as far as Ansible automation is concerned is the venerable and incredibly popular OpenSSH package, which comes in both client and server flavors.

Support for automating tasks on Windows using SSH as the transport rather than WinRM was added in Ansible 2.8 – however, it should be noted that there are many warnings about this support in the official Ansible documentation – support is described as experimental, and users are warned that things might change in the future in a way that is not backward compatible. In addition, developers expect to uncover more bugs as they continue their testing.

For these reasons, we have put a lot of effort into describing the setup of WinRM for automating Windows hosts with Ansible. Nonetheless...