Hi Jordan,

Got back to that now. Joined forces with other team members but it just 
doesn't work.
We always get the error message:
ConnectionError: SOCKSHTTPConnectionPool(host='*.*.*.*', port=5985): Max 
retries exceeded with url: /wsman (Caused by 
NewConnectionError('<urllib3.contrib.socks.SOCKSConnection object at 
0x7f7fbe844450>: Failed to establish a new connection: [Errno 111] 
Connection ref
used',))

We've tried lots of stuff. Both ports (5985 and 5986). We've set the 
following parameters in the playbook:
    ansible_user: Administrator
    ansible_password: ********
    ansible_psrp_proxy: socks5h://0.0.0.0:1234
    ansible_connection: psrp
    ansible_psrp_protocol: http
    ansible_port: 5985

We've also tried:
    ansible_psrp_max_envelope_size: 1536000

We've also tried socks5 instead of socks5h

As for ssh configurations, we've used the following:
Host 10.0.*.*
  ProxyCommand ssh -CfN -D 0.0.0.0:1234 -p 22 -W %h:%p ubuntu@bastion
  IdentityFile ~/.ssh/keyFile.pem
  StrictHostKeyChecking no
  UserKnownHostsFile /dev/null

Host bastion
  Hostname  <bastion IP>
  User ubuntu
  IdentityFile ~/.ssh/keyFile.pem
  ControlMaster auto
  ControlPath ~/.ssh/ansible-%r@%h:%p
  ControlPersist 5
  StrictHostKeyChecking no
  UserKnownHostsFile /dev/null

What else are we missing here? Everything works from inside a docker 
container. The bastion is an AWS instance and the remote machine is also an 
AWS instance.
We thought that it might be a firewall on the way so we've created a 
another AWS instance and run everything from there. Nothing!

Do you have any other suggestions?

Thanks
Gil

On Monday, 15 October 2018 01:17:15 UTC+3, Jordan Borean wrote:
>
> Hey Gil (and anyone else interested)
>
> I finally was able to document this a bit more thoroughly with a step by 
> step example at 
> http://www.bloggingforlogging.com/2018/10/14/windows-host-through-ssh-bastion-on-ansible/.
>  
> No idea if you are still working on this but potentially you need to define 
> the proxy with the schema "socks5h://", the extra h on the end means all 
> DNS resolution is done on the bastion host and not the Ansible client.
>
> Thanks
>
> Jordan
>

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