trying vagrant + ansible for windows server target. cant win_ping

[pixel fairy]

host: ubuntu-16.04
vagrant: 2.0.4
vagrant-hostmanager (1.8.8)
vagrant-libvirt (0.0.43)
vagrant-mutate (1.2.0)
vagrant-sshfs (1.3.1)

there is a virtualbox version of the same windows box. used pip to update winrm (and also had to use pip for openssl) same results without the pywinrm warning.

VAGRANTFILE_API_VERSION = "2"

Vagrant.configure(VAGRANTFILE_API_VERSION) do |config|
  config.vm.box = "peru/windows-server-2012-r2-standard-x64-eval"
  config.vm.provider "libvirt" do |libvirt|
    libvirt.input type: "tablet", bus: "usb"
    libvirt.graphics_type = "vnc"
  end
  config.vm.provision "shell", path: "ConfigureRemotingForAnsible.ps1"
  config.vm.provision "ansible", playbook: "site.yml"
end

ansible setup script at https://github.com/ansible/ansible/blob/devel/examples/scripts/ConfigureRemotingForAnsible.ps1

site.yml:

hosts: all
  vars:
    ansible_winrm_scheme: http
    ansible_winrm_server_cert_validation: ignore
  tasks:
  - name: ping
    win_ping:

$ vagrant up

Bringing machine 'default' up with 'libvirt' provider...
==> default: Checking if box 'peru/windows-server-2012-r2-standard-x64-eval' is up to date...
==> default: Uploading base box image as volume into libvirt storage...
==> default: Creating image (snapshot of base box volume).
==> default: Creating domain with the following settings...
==> default:  -- Name:              winping_default
==> default:  -- Domain type:       kvm
==> default:  -- Cpus:              1
==> default:
==> default:  -- Feature:           acpi
==> default:  -- Feature:           apic
==> default:  -- Feature:           pae
==> default:  -- Memory:            2048M
==> default:  -- Management MAC:    
==> default:  -- Loader:            
==> default:  -- Base box:          peru/windows-server-2012-r2-standard-x64-eval
==> default:  -- Storage pool:      default
==> default:  -- Image:             /var/lib/libvirt/images/winping_default.img (50G)
==> default:  -- Volume Cache:      default
==> default:  -- Kernel:            
==> default:  -- Initrd:            
==> default:  -- Graphics Type:     vnc
==> default:  -- Graphics Port:     -1
==> default:  -- Graphics IP:       127.0.0.1
==> default:  -- Graphics Password: Not defined
==> default:  -- Video Type:        qxl
==> default:  -- Video VRAM:        9216
==> default:  -- Sound Type:    ich6
==> default:  -- Keymap:            en-us
==> default:  -- TPM Path:          
==> default:  -- INPUT:             type=tablet, bus=usb
==> default:  -- CHANNEL:             type=unix, mode=
==> default:  -- CHANNEL:             target_type=virtio, target_name=org.qemu.guest_agent.0
==> default:  -- CHANNEL:             type=spicevmc, mode=
==> default:  -- CHANNEL:             target_type=virtio, target_name=com.redhat.spice.0
==> default:  -- RNG device model:  random
==> default: Creating shared folders metadata...
==> default: Starting domain.
==> default: Waiting for domain to get an IP address...
==> default: Waiting for SSH to become available...
==> default: Forwarding ports...
==> default: 3389 (guest) => 3389 (host) (adapter eth0)
==> default: 5986 (guest) => 5986 (host) (adapter eth0)
==> default: 5985 (guest) => 55985 (host) (adapter eth0)
==> default: Configuring and enabling network interfaces...
==> default: Running provisioner: shell...
    default: Running: ConfigureRemotingForAnsible.ps1 as c:\tmp\vagrant-shell.ps1
==> default: Running provisioner: ansible...
Vagrant has automatically selected the compatibility mode '2.0'
according to the Ansible version installed (2.5.1).

Alternatively, the compatibility mode can be specified in your Vagrantfile:
https://www.vagrantup.com/docs/provisioning/ansible_common.html#compatibility_mode

    default: Running ansible-playbook...

PLAY [all] *********************************************************************

TASK [Gathering Facts] *********************************************************
 [WARNING]: ansible_winrm_server_cert_validation unsupported by pywinrm (is an
up-to-date version of pywinrm installed?)

fatal: [default]: UNREACHABLE! => {"changed": false, "msg": "plaintext: [Errno 104] Connection reset by peer", "unreachable": true}
    to retry, use: --limit @/home/shared/vagrant/winping/site.retry

PLAY RECAP *********************************************************************
default                    : ok=0    changed=0    unreachable=1    failed=0  

Ansible failed to complete successfully. Any error output should be
visible above. Please fix these errors and try again.

also tried with ansible_winrm_scheme: https

==> default: Running provisioner: shell...
    default: Running: ConfigureRemotingForAnsible.ps1 as c:\tmp\vagrant-shell.ps1
==> default: Running provisioner: ansible...
Vagrant has automatically selected the compatibility mode '2.0'
according to the Ansible version installed (2.5.1).

Alternatively, the compatibility mode can be specified in your Vagrantfile:
https://www.vagrantup.com/docs/provisioning/ansible_common.html#compatibility_mode

    default: Running ansible-playbook...

PLAY [all] *********************************************************************

TASK [Gathering Facts] *********************************************************
 [WARNING]: ansible_winrm_server_cert_validation unsupported by pywinrm (is an
up-to-date version of pywinrm installed?)

fatal: [default]: UNREACHABLE! => {"changed": false, "msg": "ssl: 500 WinRMTransport. [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:590)", "unreachable": true}
    to retry, use: --limit @/home/shared/vagrant/winping/site.retry

PLAY RECAP *********************************************************************
default                    : ok=0    changed=0    unreachable=1    failed=0  

Ansible failed to complete successfully. Any error output should be
visible above. Please fix these errors and try again.

[Tom Rota]

Have you tried letting vagrant bring the box up without running the ansible portion of provisioning, getting your command prompt back, and then running ansible-playbook site.yml -vvvvv ?

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[pixel fairy]

Yes, but without so much verbose.

turns out to be a known bug in pywinrm, fixed in current tree. installing from github fixed it.

if you have the same problem, wait till pywinrm-0.3.1 (or whatever version) is out, or

git clone https://github.com/diyan/pywinrm
cd pywinrm
pip install --upgrade .

then just pip upgrade as usual when the fix is released.