Ansible has a fairly minimal set of system requirements—as such, you should find that if you have a machine (either a laptop, a server, or a virtual machine) that is capable of running Python, then you will be able to run Ansible on it. Later in this chapter, we will demonstrate the installation methods for Ansible on a variety of operating systems—it is hence left to you to decide which operating systems are right for you.

The one exception to the preceding statement is Microsoft Windows—although there are Python environments available for Windows, there is as yet no native build of Ansible for Windows. Readers running more recent versions of Windows will be able to install Ansible using Windows Subsystem for Linux (henceforth, WSL) and by following the procedures outlined later for their chosen WSL environment (for example, if you install Ubuntu on WSL, you should simply follow the instructions given in this chapter for installing Ansible on Ubuntu).

Ansible is written in Python and, as such, can be run on a wide range of systems. This includes most popular flavors of Linux, FreeBSD, and macOS. The one exception to this is Windows, where though native Python distributions exist, there is as yet no native Ansible build. As a result, your best option at the time of writing is to install Ansible under WSL proceeding as if you were running on a native Linux host.

Once you have established the system on which you wish to run Ansible, the installation process is normally simple and straightforward. In the following sections, we will discuss how to install Ansible on a wide range of different systems, so that most readers should be able to get up and running with Ansible in a matter of minutes.

The release cycle for Ansible is usually about four months, and during this short release cycle, there are normally many changes, from minor bug fixes to major ones, to new features and even sometimes fundamental changes to the language. The simplest way to not only get up and running with Ansible but to keep yourself up to date is to use the native packages built for your operating system where they are available.

For example, if you wish to run the latest version of Ansible on top of Linux distribution such as CentOS, Fedora, Red Hat Enterprise Linux (RHEL), Debian, and Ubuntu, I strongly recommend that you use an operating system package manager such as yum on Red Hat-based distributions or apt on Debian-based ones. In this manner, whenever you update your operating system, you will update Ansible simultaneously.

Of course, it might be that you need to retain a specific version of Ansible for certain purposes—perhaps because your playbooks have been tested with this. In this instance, you would almost certainly choose an alternative installation method, but this is beyond the scope of this book. Also, it is recommended that, where possible, you create and maintain your playbooks in line with documented best practices, which should mean that they survive most Ansible upgrades.

The following are some examples showing how you might install Ansible on several Linux distributions:

• Installing Ansible on Ubuntu: To install the latest version of the Ansible control machine on Ubuntu, the apt packaging tool makes it easy using the following commands:

$ sudo apt-get update 
$ sudo apt-get install software-properties-common 
$ sudo apt-add-repository --yes --update ppa:ansible/ansible 
$ sudo apt-get install ansible

deb http://ppa.launchpad.net/ansible/ansible/ubuntu trusty main

$ sudo apt-key adv --keyserver keyserver.ubuntu.com --recv-keys 93C4A3FD7BB9C367 
$ sudo apt-get update 
$ sudo apt-get install ansible

• Installing Ansible on Gentoo: To install the latest version of the Ansible control machine on Gentoo, the portage package manager makes it easy with the following commands:

$ echo 'app-admin/ansible' >> /etc/portage/package.accept_keywords
$ emerge -av app-admin/ansible

• Installing Ansible on FreeBSD: To install the latest version of the Ansible control machine on FreeBSD, the PKG manager makes it easy with the following commands:

$ sudo pkg install py36-ansible
$ sudo make -C /usr/ports/sysutils/ansible install

• Installing Ansible on Fedora: To install the latest version of the Ansible control machine on Fedora, the dnf package manager makes it easy with the following commands:

$ sudo dnf -y install ansible

• Installing Ansible on CentOS: To install the latest version of the Ansible control machine on CentOS or RHEL, the yum package manager makes it easy with the following commands:

$ sudo yum install epel-release
$ sudo yum -y install ansible

If you execute the preceding commands on RHEL, you have to make sure that the Ansible repository is enabled. If it's not, you need to enable the relevant repository with the following commands:

$ sudo subscription-manager repos --enable rhel-7-server-ansible-2.9-rpms

• Installing Ansible on Arch Linux: To install the latest version of the Ansible control machine on Arch Linux, the pacman package manager makes it easy with the following commands:

$ pacman -S ansible

Once you have installed Ansible on the specific Linux distribution that you use, you can begin to explore. Let's start with a simple example—when you run the ansible command, you will see output similar to the following:

$ ansible --version
ansible 2.9.6
 config file = /etc/ansible/ansible.cfg
 configured module search path = [u'/home/jamesf_local/.ansible/plugins/modules', u'/usr/share/ansible/plugins/modules']
 ansible python module location = /usr/lib/python2.7/dist-packages/ansible
 executable location = /usr/bin/ansible
 python version = 2.7.17 (default, Nov 7 2019, 10:07:09) [GCC 9.2.1 20191008]

$ git clone https://github.com/ansible/ansible.git
$ cd ./ansible
$ make rpm
$ sudo rpm -Uvh ./rpm-build/ansible-*.noarch.rpm

Now that you have seen how to install Ansible on Linux, we'll take a brief look at how to install Ansible on macOS.

In this section, you will learn how to install Ansible on macOS. The easiest installation method is to use Homebrew, but you could also use the Python package manager. Let's get started by installing Homebrew, which is a fast and convenient package management solution for macOS.

If you don't already have Homebrew installed on macOS, you can easily install it as detailed here:

• Installing Homebrew: Normally the two commands shown here are all that is required to install Homebrew on macOS:

$ xcode-select --install
$ ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)"

If you have already installed the Xcode command-line tools for another purpose, you might see the following error message:

xcode-select: error: command line tools are already installed, use "Software Update" to update

You may want to open the App Store on macOS and check whether updates to Xcode are required, but as long as the command-line tools are installed, your Homebrew installation should proceed smoothly.

If you wish to confirm that your installation of Homebrew was successful, you can run the following command, which will warn you about any potential issues with your install—for example, the following output is warning us that, although Homebrew is installed successfully, it is not in our PATH and so we may not be able to run any executables without specifying their absolute path:

$ brew doctor
Please note that these warnings are just used to help the Homebrew maintainers
with debugging if you file an issue. If everything you use Homebrew for is
working fine: please don't worry or file an issue; just ignore this. Thanks!

Warning: Homebrew's sbin was not found in your PATH but you have installed
formulae that put executables in /usr/local/sbin.
Consider setting the PATH for example like so
 echo 'export PATH="/usr/local/sbin:$PATH"' >> ~/.bash_profile

• Installing the Python package manager (pip): If you don't wish to use Homebrew to install Ansible, you can instead install pip using with the following simple commands:

$ sudo easy_install pip

Also check that your Python version is at least 2.7, as Ansible won't run on anything older (this should be the case with almost all modern installations of macOS):

$ python --version
Python 2.7.16

You can use either Homebrew or the Python package manager to install the latest version of Ansible on macOS as follows:

• Installing Ansible via Homebrew: To install Ansible via Homebrew, run the following command:

$ brew install ansible

• Installing Ansible via the Python package manager (pip): To install Ansible via pip, use the following command:

$ sudo pip install ansible

$ pip install git+https://github.com/ansible/ansible.git@devel 

Now that you have installed Ansible using your preferred method, you can run the ansible command as before, and if all has gone according to plan, you will see output similar to the following:

$ ansible --version
ansible 2.9.6
  config file = None
  configured module search path = ['/Users/james/.ansible/plugins/modules', '/usr/share/ansible/plugins/modules']
  ansible python module location = /usr/local/Cellar/ansible/2.9.4_1/libexec/lib/python3.8/site-packages/ansible
  executable location = /usr/local/bin/ansible
  python version = 3.8.1 (default, Dec 27 2019, 18:05:45) [Clang 11.0.0 (clang-1100.0.33.16)]

If you are running macOS 10.9, you may experience issues when installing Ansible using pip. The following is a workaround that should resolve the issue:

$ sudo CFLAGS=-Qunused-arguments CPPFLAGS=-Qunused-arguments pip install ansible

If you want to update your Ansible version, pip makes it easy via the following command:

$ sudo pip install ansible --upgrade

Similarly, you can upgrade it using the brew command if that was your install method:

$ brew upgrade ansible

Now that you have learned the steps to install Ansible on macOS, let's see how to configure a Windows host for automation with Ansible.

As discussed earlier, there is no direct installation method for Ansible on Windows—simply, it is recommended that, where available, you install WSL and install Ansible as if you were running Linux natively, using the processes outlined earlier in this chapter.

Despite this limitation, however, Ansible is not limited to managing just Linux- and BSD-based systems—it is capable of the agentless management of Windows hosts using the native WinRM protocol, with modules and raw commands making use of PowerShell, which is available in every modern Windows installation. In this section, you will learn how to configure Windows to enable task automation with Ansible.

Let's look at what Ansible is capable of when automating Windows hosts:

• Gather facts about remote hosts.
• Install and uninstall Windows features.
• Manage and query Windows services.
• Manage user accounts and a list of users.
• Manage packages using Chocolatey (a software repository and accompanying management tool for Windows).
• Perform Windows updates.
• Fetch multiple files from a remote machine to the Windows host.
• Execute raw PowerShell commands and scripts on target hosts.

Ansible allows you to automate tasks on Windows machines by connecting with either a local user or a domain user. You can run actions as an administrator using the Windows runas support, just as with the sudo command on Linux distributions.

Also, as Ansible is open source software, it is easy to extend its functionality by creating your own modules in PowerShell or even sending raw PowerShell commands. For example, an InfoSec team could manage filesystem ACLs, configure Windows Firewall, and manage hostnames and domain membership with ease, using a mix of native Ansible modules and, where necessary, raw commands.

The Windows host must meet the following requirements for the Ansible control machine to communicate with it:

• Ansible attempts to support all Windows versions that are under either current or extended support from Microsoft, including desktop platforms such as Windows 7, 8.1, and 10, along with server operating systems including Windows Server 2008 (and R2), 2012 (and R2), 2016, and 2019.
• You will also need to install PowerShell 3.0 or later and at least .NET 4.0 on your Windows host.
• You will need to create and activate a WinRM listener, which is described in detail later. For security reasons, this is not enabled by default.

Let's look in more detail at how to prepare a Windows host to be automated by Ansible:

1. With regard to prerequisites, you have to make sure PowerShell 3.0 and .NET Framework 4.0 are installed on Windows machines. If you're still using the older version of PowerShell or .NET Framework, you need to upgrade them. You are free to perform this manually, or the following PowerShell script can handle it automatically for you:

$url = "https://raw.githubusercontent.com/jborean93/ansible-windows/master/scripts/Upgrade-PowerShell.ps1" 
$file = "$env:temp\Upgrade-PowerShell.ps1" (New-Object -TypeName System.Net.WebClient).DownloadFile($url, $file) 

Set-ExecutionPolicy -ExecutionPolicy Unrestricted -Force &$file -Verbose Set-ExecutionPolicy -ExecutionPolicy Restricted -Force

This script works by examining the programs that need to be installed (such as .NET Framework 4.5.2) and the required PowerShell version, rebooting if required, and setting the username and password parameters. The script will automatically restart and log on at reboot so that no more action is required and the script will continue until the PowerShell version matches the target version.

If the username and password parameters aren't set, the script will ask the user to reboot and log in manually if necessary, and the next time the user logs in, the script will continue at the point where it was interrupted. The process continues until the host meets the requirements for Ansible automation.

2. When PowerShell has been upgraded to at least version 3.0, the next step will be to configure the WinRM service so that Ansible can connect to it. WinRM service configuration defines how Ansible can interface with the Windows hosts, including the listener port and protocol.

If you have never set up a WinRM listener before, you have three options to do this:

• Firstly, you can use winrm quickconfig for HTTP and winrm quickconfig -transport:https for HTTPS. This is the simplest method to use when you need to run outside of the domain environment and just create a simple listener. This process has the advantage of opening the required port in the Windows firewall and automatically starting the WinRM service.
• If you are running in a domain environment, I strongly recommend using Group Policy Objects (GPOs) because if the host is the domain member, then the configuration is done automatically without user input. There are many documented procedures for doing this available, and as this is a very Windows domain-centric task, it is beyond the scope of this book.
• Finally, you can create a listener with a specific configuration by running the following PowerShell commands:

$selector_set = @{
    Address = "*"
    Transport = "HTTPS"
}
$value_set = @{
    CertificateThumbprint = "E6CDAA82EEAF2ECE8546E05DB7F3E01AA47D76CE"
}

New-WSManInstance -ResourceURI "winrm/config/Listener" -SelectorSet $selector_set -ValueSet $value_set

$url = "https://raw.githubusercontent.com/jborean93/ansible-windows/master/scripts/Install-WMF3Hotfix.ps1" 
$file = "$env:temp\Install-WMF3Hotfix.ps1" 

(New-Object -TypeName System.Net.WebClient).DownloadFile($url, $file) powershell.exe -ExecutionPolicy ByPass -File $file -Verbose

winrm enumerate winrm/config/Listener

If all goes well, you should have output similar to this:

Listener
    Address = *
    Transport = HTTP
    Port = 5985
    Hostname
    Enabled = true
    URLPrefix = wsman
    CertificateThumbprint
    ListeningOn = 10.0.2.15, 127.0.0.1, 192.168.56.155, ::1, fe80::5efe:10.0.2.15%6, fe80::5efe:192.168.56.155%8, fe80::
ffff:ffff:fffe%2, fe80::203d:7d97:c2ed:ec78%3, fe80::e8ea:d765:2c69:7756%7

Listener
    Address = *
    Transport = HTTPS
    Port = 5986
    Hostname = SERVER2016
    Enabled = true
    URLPrefix = wsman
    CertificateThumbprint = E6CDAA82EEAF2ECE8546E05DB7F3E01AA47D76CE
    ListeningOn = 10.0.2.15, 127.0.0.1, 192.168.56.155, ::1, fe80::5efe:10.0.2.15%6, fe80::5efe:192.168.56.155%8, fe80::
ffff:ffff:fffe%2, fe80::203d:7d97:c2ed:ec78%3, fe80::e8ea:d765:2c69:7756%7

According to the preceding output, two listeners are active—one to listen on port 5985 over HTTP and the other to listen on port 5986 over HTTPS providing greater security. By way of additional explanation, the following parameters are also displayed in the preceding output:

• Transport: This should be set to either HTTPS or HTTPS, though it is strongly recommended that you use the HTTPS listener to ensure your automation commands are not subject to snooping or manipulation.
• Port: This is the port on which the listener operates, by default 5985 for HTTP or 5986 for HTTPS.
• URLPrefix: This is the URL prefix to communicate with, by default, wsman. If you change it, you must set the ansible_winrm_path host on your Ansible control host to the same value.
• CertificateThumbprint: If running on an HTTPS listener, this is the certificate thumbprint of the Windows Certificate Store used by the connection.

# test out HTTP
winrs -r:http://<server address>:5985/wsman -u:Username -p:Password ipconfig

# test out HTTPS (will fail if the cert is not verifiable)
winrs -r:https://<server address>:5986/wsman -u:Username -p:Password -ssl ipconfig 

# test out HTTPS, ignoring certificate verification
$username = "Username"
$password = ConvertTo-SecureString -String "Password" -AsPlainText -Force
$cred = New-Object -TypeName System.Management.Automation.PSCredential -ArgumentList $username, $password

$session_option = New-PSSessionOption -SkipCACheck -SkipCNCheck -SkipRevocationCheck
Invoke-Command -ComputerName server -UseSSL -ScriptBlock { ipconfig } -Credential $cred -SessionOption $session_option

$ pip install winrm

[windows]
192.168.1.52

[windows:vars]
ansible_user=administrator
ansible_password=password
ansible_connection=winrm
ansible_winrm_server_cert_validation=ignore

$ ansible -i inventory -m ping windows
192.168.1.52 | SUCCESS => {
    "changed": false,
    "ping": "pong"
}