diff --git a/docs/ansible.md b/docs/ansible.md
new file mode 100644
index 000000000..60480a608
--- /dev/null
+++ b/docs/ansible.md
@@ -0,0 +1,60 @@
+# Running this playbook
+
+This playbook is meant to be run using [Ansible](https://www.ansible.com/).
+
+
+## Supported Ansible versions
+
+Generally, Ansible 2.4 or later is required.
+
+If you're on Ansible 2.5.x, then at least Ansible 2.5.2 is required.
+
+
+## Checking your Ansible version
+
+In most cases, you won't need to worry about the Ansible version.
+The playbook will try to detect it and tell you if you're on an unsupported version.
+
+To manually check which verison of Ansible you're on, run: `ansible --version`.
+
+If you're on an old version of Ansible, you should upgrade to a newer version.
+
+
+## Upgrading Ansible
+
+Depending on your distribution, you may be able to upgrade Ansible in a few different ways:
+
+- by using an additional repository (PPA, etc.), which provides newer Ansible versions
+
+- by removing the Ansible package (`yum remove ansible` or `apt-get remove ansible`) and installing via [pip](https://pip.pypa.io/en/stable/installing/) (`pip install ansible`).
+
+If using the `pip` method, do note that the `ansible-playbook` binary may not be on the `$PATH` (https://linuxconfig.org/linux-path-environment-variable), but in some more special location like `/usr/local/bin/ansible-playbook`. You may need to invoke it using the full path.
+
+
+**Note**: Both of the above methods are a bad way to run system software such as Ansible.
+If you find yourself needing to resort to such hacks, please consider reporting a bug to your distribution and/or switching to a sane distribution, which provides up-to-date software.
+
+
+## Using Ansible via Docker
+
+Alternatively, you can run Ansible itself from a Docker container on your computer.
+
+Here's a sample command to get you started (run this from the playbook's directory):
+
+```bash
+docker run -it --rm \
+-w /work \
+-v `pwd`:/work \
+-v $HOME/.ssh/id_rsa:/root/.ssh/id_rsa:ro \
+--entrypoint=/bin/sh \
+qmxme/ansible
+```
+
+The above command tries to mount an SSH key (`$HOME/.ssh/id_rsa`) into the container (at `/root/.ssh/id_rsa`).
+If your SSH key is at a different path (not in `$HOME/.ssh/id_rsa`), adjust that part.
+If you don't use SSH keys for authentication, simply remove that whole line (`-v $HOME/.ssh/id_rsa:/root/.ssh/id_rsa:ro`).
+
+Once you execute the above command, you'll be dropped into a `/work` directory inside a Docker container.
+The `/work` directory contains the playbook's code.
+
+You can execute `ansible-playbook` commands as per normal now.
\ No newline at end of file
diff --git a/docs/prerequisites.md b/docs/prerequisites.md
index 8895db06e..13cf89a5c 100644
--- a/docs/prerequisites.md
+++ b/docs/prerequisites.md
@@ -4,7 +4,7 @@
 
 - [Python](https://www.python.org/) being installed on the server. Most distributions install Python by default, but some don't (e.g. Ubuntu 18.04) and require manual installation (something like `apt-get install python`).
 
-- the [Ansible](http://ansible.com/) program being installed on your own computer. It's used to run this playbook and configures your server for you. Version 2.4 or later is required (see `ansible --version`).
+- the [Ansible](http://ansible.com/) program being installed on your own computer. It's used to run this playbook and configures your server for you. Take a look at [our guide about Ansible](ansible.md) for version requirements or alternative ways to run Ansible.
 
 - properly configured DNS SRV record for `<your-domain>` (details in [Configuring DNS](configuring-dns.md#configuring-dns) below)
 
diff --git a/roles/matrix-server/tasks/setup/setup_sanity_check.yml b/roles/matrix-server/tasks/setup/setup_sanity_check.yml
index bb048a204..4d9679122 100644
--- a/roles/matrix-server/tasks/setup/setup_sanity_check.yml
+++ b/roles/matrix-server/tasks/setup/setup_sanity_check.yml
@@ -1,5 +1,20 @@
 ---
 
+- set_fact:
+    matrix_ansible_outdated_fail_msg: "You are running on Ansible {{ ansible_version.string }}, which is not supported. See our guide about Ansible: https://github.com/spantaleev/matrix-docker-ansible-deploy/blob/master/docs/ansible.md"
+
+- name: Fail if running on Ansible < 2.4
+  fail:
+    msg: "{{ matrix_ansible_outdated_fail_msg }}"
+  when: "ansible_version.major <= 2 and ansible_version.minor < 4"
+
+# Ansible 2.5.0 and 2.5.1 are known to have a bug with `include_tasks` + `with_items`.
+# The bug has been fixed in Ansible 2.5.2.
+- name: Fail if running on Ansible 2.5.x (lower than 2.5.2)
+  fail:
+    msg: "{{ matrix_ansible_outdated_fail_msg }}"
+  when: "ansible_version.major == 2 and ansible_version.minor == 5 and ansible_version.revision < 2"
+
 - name: Fail if Macaroon key is missing
   fail:
     msg: "You need to set a secret in the matrix_synapse_macaroon_secret_key variable"
@@ -21,4 +36,4 @@
   with_items:
     - "{{ hostname_identity }}"
     - "{{ hostname_matrix }}"
-    - "{{ hostname_riot }}"
\ No newline at end of file
+    - "{{ hostname_riot }}"