How do I configure a jump host to access Windows servers that I have no direct access to?
The Ansible documentation explains how to do this for Linux but doesn't mention how to achieve something similar when using WinRM against Windows servers.
You can send winrm traffic thru a proxy such as nginx since it's just basic https traffic. If you set up a rule per "target node" in your nginx config so that each node gets a unique url (proxy.domain.com/node1, proxy.domain.com/node2 etc) and each node points to real.fqdn.com/wsman) you will be able to proxy multiple winrm connections thru one jump host. This was discussed in the following PR: https://github.com/ansible/ansible/pull/12054