How to configure Ansible to manage Windows Hosts on Ubuntu 16.04

Note: This section assumes you already have ansible installed, working, active directory setup, and test windows host in communication with AD. Although its not needed to have AD. Its good practice for to have it all setup talking to each other for learning. 


Now Ansible does not come with windows managing ability out of the box. Its is easier to setup on centos as the packages are better maintained on Redhat distros. However if you want to set it up on Ubuntu here is what you need to do.

  • easy_install pip
  • pip install –upgrade pip
  • pip install pywinrm
  • apt-get install python-pip
  • apt-get install python-devel krb5-devel krb5-libs krb5-workstation
  • apt-get install python-devel
  • apt-get install python-de
  • apt-get install python-dev
  • apt-get install  libkrb5-dev
  • apt-get install bind9
  • pip install pywinrm[Kerberos]
  • apt-get install krb5-kdc krb5-admin-server

Next Setup your /etc/krb5.conf

default = FILE:/var/log/krb5libs.log
kdc = FILE:/var/log/krb5kdc.log
admin_server = FILE:/var/log/kadmind.log
default_realm = HOME.NICKTAILOR.COM
dns_lookup_realm = false
dns_lookup_kdc = false
ticket_lifetime = 24h
renew_lifetime = 7d
forwardable = true
admin_server = HOME.NICKTAILOR.COM

Test Kerberos

Run the following commands to test Kerberos:

kinit administrator@HOME.NICKTAILOR.COM <–make sure you do this exact case sensitive or your authenication will fail. Also the user has to have domain admin privileges. 

You will be prompted for the administrator password klist
You should see a Kerberos KEYRING record.

[root@localhost win_playbooks]# klist
Ticket cache: FILE:/tmp/krb5cc_0Default principal: administrator@HOME.NICKTAILOR.COM
Valid starting       Expires              Service principal05/23/2018 14:20:50  05/24/2018 00:20:50  krbtgt/HOME.NICKTAILOR.COM@HOME.NICKTAILOR.COM renew until 05/30/2018 14:20:40

Configure Ansible

Ansible is complex and is sensitive to the environment. Troubleshooting an environment which has never initially worked is complex and confusing. We are going to configure Ansible with the least complex possible configuration. Once you have a working environment, you can make extensions and enhancements in small steps.

The core configuration of Ansible resides at /etc/ansible

We are only going to update two files for this exercise.

Update the Ansible Inventory file

Edit /etc/ansible/hosts and add:



“[windows]” is a created group of servers called “windows”. In reality this should be named something more appropriate for a group which would have similar configurations, such as “Active Directory Servers”, or “Production Floor Windows 10 PCs”, etc.

Update the Ansible Group Variables for Windows

Ansible Group Variables are variable settings for a specific inventory group. In this case, we will create the group variables for the “windows” servers created in the /etc/ansible/hosts file.

Create /etc/ansible/group_vars/windows and add:

ansible_user: Administrator

ansible_password: Abcd1234 (You dont need this really if you ran kinit already) 

ansible_port: 5986

ansible_connection: winrm

ansible_winrm_server_cert_validation: ignore

This is a YAML configuration file, so make sure the first line is three dashes “‐‐‐”

Naturally change the Administrator password to the password for WinServer1.

For best practices, Ansible can encrypt this file into the Ansible Vault. This would prevent the password from being stored here in clear text. For this lab, we are attempting to keep the configuration as simple as possible. Naturally in production this would not be appropriate.

The powershell script must be run on the windows client in order for ansible to be table to talk to the host without issues.

Configure Windows Servers to Manage

To configure the Windows Server for remote management by Ansible requires a bit of work. Luckily the Ansible team has created a PowerShell script for this. Download this script from [here] to each Windows Server to manage and run this script as Administrator.

Log into WinServer1 as Administrator, download ConfigureRemotingForAnsible.ps1 and run this PowerShell script without any parameters.

Once this command has been run on the WinServer1, return to the Ansible1 Controller host.

Test Connectivity to the Windows Server

If all has gone well, we should be able to perform an Ansible PING test command. This command will simply connect to the remote WinServer1 server and report success or failure.

ansible windows -m win_ping

This command runs the Ansible module “win_ping” on every server in the “windows” inventory group.

Type: ansible windows -m setup to retrieve a complete configuration of Ansible environmental settings.

Type: ansible windows -c ipconfig

If this command is successful, the next steps will be to build Ansible playbooks to manage Windows Servers.

Managing Windows Servers with Playbooks


Let’s create some playbooks and test Ansible for real on Windows systems.

Create a folder on Ansible1 for the playbooks, YAML files, modules, scripts, etc. For these exercises we created a folder under /root called win_playbooks.

Ansible has some expectations on the directory structure where playbooks reside. Create the library and scripts folders for use later in this exercise.


cd /root

mkdir win_playbooks

mkdir win_playbooks/library

mkdir win_playbooks/scripts

Create the first playbook example “netstate.yml”
The contents are:

– name: test cmd from win_command module

  hosts: windows


    – name: run netstat and return Ethernet stats

      win_command: netstat -e

      register: netstat

    – debug: var=netstat

This playbook does only one task, to connect to the servers in the Ansible inventory group “windows” and run the command netstat.exe -a and return the results.

To run this playbook, run this command on Ansible1:


Errors that I ran into

Now on ubuntu you might get some SSL error when trying to run a win_ping or windows playbook. This is because the python libraries are trying to verify the self signed cert before opening a secure connection via https. Not sure why this hasnt been updated in ubuntu. Should be fine on centos. But here is the work around.

ansible windows -m win_ping

Wintestserver1 | UNREACHABLE! => {
“changed”: false,
“msg”: “ssl: 500 WinRMTransport. [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:590)”,
“unreachable”: true

How you can get around the is update the python library to not care about looking for a valid cert and just open a secure connection.

Edit  /usr/lib/python2.7/


import ssl


    _create_unverified_https_context = ssl._create_unverified_context

except AttributeError:

    # Legacy Python that doesn’t verify HTTPS certificates by default



    # Handle target environment that doesn’t support HTTPS verification

    ssl._create_default_https_context = _create_unverified_https_context


Then it should look like this

ansible windows -m win_ping

wintestserver1 | SUCCESS => {
“changed”: false,
“ping”: “pong”

Proxies and WSUS:

If you are using these and you want to disable proxies check on your host simply export

export no_proxy=, winserver1, etc,

Or add a file in /etc/profile.d/

If you have WSUS configured you will need to check to see if there are updates from there or they will not show when the yaml searches for new updates.

Test windows updates yaml: The formatting is all wrong below so click on the link and it will have the proper formatted yaml for windows update.

– hosts: windows
gather_facts: no

– name: Search Windows Updates
– SecurityUpdates
– CriticalUpdates
– UpdateRollups
– Updates
state: searched
log_path: C:\ansible_wu.txt

– name: Install updates
– SecurityUpdates
– CriticalUpdates
– UpdateRollups
– Updates


If it works properly the log file on the test host will have something like the following: C:\ansible_wu.txt

Logs show the update

2018-06-04 08:47:54Z Creating Windows Update session…
2018-06-04 08:47:54Z Create Windows Update searcher…
2018-06-04 08:47:54Z Search criteria: (IsInstalled = 0 AND CategoryIds contains ‘0FA1201D-4330-4FA8-8AE9-B877473B6441’) OR(IsInstalled = 0 AND CategoryIds contains ‘E6CF1350-C01B-414D-A61F-263D14D133B4′) OR(IsInstalled = 0 AND CategoryIds contains ’28BC880E-0592-4CBF-8F95-C79B17911D5F’) OR(IsInstalled = 0 AND CategoryIds contains ‘CD5FFD1E-E932-4E3A-BF74-18BF0B1BBD83’)
2018-06-04 08:47:54Z Searching for updates to install in category Ids 0FA1201D-4330-4FA8-8AE9-B877473B6441 E6CF1350-C01B-414D-A61F-263D14D133B4 28BC880E-0592-4CBF-8F95-C79B17911D5F CD5FFD1E-E932-4E3A-BF74-18BF0B1BBD83…
2018-06-04 08:48:33Z Found 2 updates
2018-06-04 08:48:33Z Creating update collection…
2018-06-04 08:48:33Z Adding update 67a00639-09a1-4c5f-83ff-394e7601fc03 – Security Update for Windows Server 2012 R2 (KB3161949)
2018-06-04 08:48:33Z Adding update ba0f75ff-19c3-4cbd-a3f3-ef5b5c0f88bf – Security Update for Windows Server 2012 R2 (KB3162343)
2018-06-04 08:48:33Z Calculating pre-install reboot requirement…
2018-06-04 08:48:33Z Check mode: exiting…
2018-06-04 08:48:33Z Return value:
“updates”: {
“67a00639-09a1-4c5f-83ff-394e7601fc03”: {
“title”: “Security Update for Windows Server 2012 R2 (KB3161949)”,
“id”: “67a00639-09a1-4c5f-83ff-394e7601fc03”,
“installed”: false,
“kb”: [
“ba0f75ff-19c3-4cbd-a3f3-ef5b5c0f88bf”: {
“title”: “Security Update for Windows Server 2012 R2 (KB3162343)”,
“id”: “ba0f75ff-19c3-4cbd-a3f3-ef5b5c0f88bf”,
“installed”: false,
“kb”: [
“found_update_count”: 2,
“changed”: false,
“reboot_required”: false,
“installed_update_count”: 0,
“filtered_updates”: {


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