How to update my hacking rig (Linux and Windows) using ansible. #ansible #ubuntu #linux #infosec #windowsupdate #hacker #automation

I have my vm:s up and running now, but I like my rig to be patched and updated, even if I only have 7 machines I want to centralize update procedure. I have chosen to do this with Ansible. As this is a demo site that I am setting up. Security of some configuration is not the best, but in this case I do not care. This is a proof of concept not a customer installation. I am also new at Ansible, but I love to know more.

Lets start with a picture:

Ansible and my ansible clients.

The linux client was really easy to implement even if I never seen this before. So we start with that. Kali is the client and Ansible is the server.

What do you need on the Ansible server

  1. Ansible
  2. ssh access with keys to the ansible clients (kali)

What do you need on the clients that you want to patch with Ansible?

  1. Create a user (in my case ansible)
  2. Configure ssh login from ansible machine with keys
  3. The ansible user on the clients need to be able to get to root

First we start with the ansible server

  1. Install Ansible
sudo apt install ansible
Install Ansible

Is Ansible installed?

Thats it from the server side right know. Even I solved that one!

Ansible clients we want updates on.

  1. Enable ssh
  2. Add user ansible
Add user ansible

3. Then we need to make the ansible user ability to sudo without password.

echo "ansible ALL=(ALL) NOPASSWD:ALL" | sudo tee /etc/sudoers.d/ansible

From the ansible server

ssh-copy-id ansible@kali

Now the Ansible user from Ansible server can access the kali box thru ssh with private and public key.

From the Ansible server try it.

ssh ansible@kali
ssh from ansible to kali box

Time to configure Ansible server

  1. Log in on ansible server as ansible
  2. create a directory (jobs)
  3. Go to jobs directory
  4. create a file named linux-hosts
  5. create a file named linux-update.yml
  6. create a file named linux-autoremove.yml

Content of the linux-host file:

#set up ssh user name and pyhton#
ansible_python_interpreter='/usr/bin/env python3'

#ip or server name

Content of the linux-update file:

linux-update file

Time to update all servers at the same time! And 5 server out of 6 had update that installed in one command.

ansible-playbook -i ./linux-hosts linux-update.yml

Now you want to do autoremove of old packages! Like you do with apt autoremove

The content of the linux-autoremove


Time to clean the clients of application that are not needed!

ansible-playbook -i ./linux-hosts linux-autoremove.yml


Time to update my Windows 10 box

On the ansible server we need to install ansible package:

ansible-galaxy collection install

On the Windows 10 box we need to do some unsecure stuff!

Start PowerShell as Administrator and past below:

Set-ExecutionPolicy Bypass -Scope Process -Force; [System.Net.ServicePointManager]::SecurityProtocol = [System.Net.ServicePointManager]::SecurityProtocol -bor 3072; iex ((New-Object System.Net.WebClient).DownloadString(''))

In the same Powershell shell type the following

winrm quickconfig

reg add "HKLM\Software\Microsoft\Windows\CurrentVersion\Policies\System\CredSSP\Parameters" /f /v AllowEncryptionOracle /t REG_DWORD /d 2

Set-Item -Path WSMan:\localhost\Service\Auth\Basic -Value $true

$url = ""

$file = "$env:temp\ConfigureRemotingForAnsible.ps1"

(New-Object -TypeName System.Net.WebClient).DownloadFile($url, $file)

powershell.exe -ExecutionPolicy ByPass -File $file

winrm enumerate winrm/config/Listener
Commands like a picture

Now it is time to create som files for Ansible. I ended up ing it like this:

On the Ansible server with ansible username under jobs directory I created a file win-hosts:


Then we need to create playbookfile

ansible@ansible:~/jobs$ cat windows_baseline.yaml

name: Windows Baseline
hosts: “{{ target }}”
connection: winrm
gather_facts: true
ansible_user: “{{ user }}”
ansible_password: “{{ password }}”
ansible_connection: winrm
ansible_winrm_transport: basic
ansible_winrm_server_cert_validation: ignore tasks:

name: Install Baseline Packages
name: install

name: Perform Updates
name: updates


Create these two directory under jobs

mkdir -p roles/install/tasks
mkdir -p roles/updates/tasks
Then create two files
main.yaml under these directory
vi roles/install/tasks/main.yaml
vi roles/updates/tasks/main.yaml

Finaly we can try this autmation of updates. Yes we have only one machine. But just add more then.

ansible-playbook -i ./win-hosts -e target=windows -e user=ansible -e password=secret  windows_baseline.yaml
Windows update with ansible

Now we have patched our hacking rig. Both Windows and Linux machine with ansible!

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