diff --git a/CHANGELOG.md b/CHANGELOG.md
index 5d09762fe..4e456a286 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,3 +1,36 @@
+# 2026-03-23
+
+## Migration validation system introduced
+
+Previously, when updating your setup, you had to remember to read the [CHANGELOG](CHANGELOG.md) file or risk breakage.
+
+Now, the playbook includes a migration validation system that ensures you're aware of breaking changes before they affect your deployment.
+You're now forced to acknowledge each breaking change, unless you wish to live dangerously (see below).
+
+A new `matrix_playbook_migration_validated_version` variable has been introduced.
+
+**New users** who started from the [example `vars.yml`](examples/vars.yml) file already have this variable set and do not need to do anything.
+
+**Existing users** will need to add the following to their `vars.yml` file after reviewing all changelog entries up to now:
+
+```yml
+matrix_playbook_migration_validated_version: v2026.03.23.0
+```
+
+Going forward, whenever a breaking change is introduced the playbook will:
+
+- bump its expected version value (`matrix_playbook_migration_expected_version`), causing a discrepancy with what you validated (`matrix_playbook_migration_validated_version`)
+
+- fail when you run it with a helpful message listing what changed and linking to the relevant changelog entries
+
+After reviewing and adapting your setup, you simply update the variable to the new version.
+
+If you'd like to live dangerously and skip these checks (not recommended), you can set this once and be done with it:
+
+```yml
+matrix_playbook_migration_validated_version: "{{ matrix_playbook_migration_expected_version }}"
+```
+
 # 2026-03-19
 
 ## Matrix Authentication Service now prefers UNIX sockets for playbook-managed Postgres
diff --git a/examples/vars.yml b/examples/vars.yml
index 655e75c24..05259d65d 100644
--- a/examples/vars.yml
+++ b/examples/vars.yml
@@ -1,4 +1,9 @@
 ---
+# This variable acknowledges that you've reviewed breaking changes up to this version.
+# The playbook will fail if this is outdated, guiding you through what changed.
+# See the changelog: https://github.com/spantaleev/matrix-docker-ansible-deploy/blob/master/CHANGELOG.md
+matrix_playbook_migration_validated_version: v2026.03.23.0
+
 # The bare domain name which represents your Matrix identity.
 # Matrix user IDs for your server will be of the form (`@alice:example.com`).
 #
diff --git a/roles/custom/matrix_playbook_migration/defaults/main.yml b/roles/custom/matrix_playbook_migration/defaults/main.yml
index b12074cbc..2432996ae 100644
--- a/roles/custom/matrix_playbook_migration/defaults/main.yml
+++ b/roles/custom/matrix_playbook_migration/defaults/main.yml
@@ -1,9 +1,27 @@
-# SPDX-FileCopyrightText: 2023 - 2025 Slavi Pantaleev
+# SPDX-FileCopyrightText: 2023 - 2026 Slavi Pantaleev
 # SPDX-FileCopyrightText: 2024 Suguru Hirahara
 #
 # SPDX-License-Identifier: AGPL-3.0-or-later
 
 ---
+
+# The version that the user has validated their setup against.
+# When empty, the user will be prompted to set this variable.
+# New users should set this to the current expected version (see below).
+# See `examples/vars.yml` and `matrix_playbook_migration_expected_version` for the recommended value.
+matrix_playbook_migration_validated_version: ''
+
+# The version that the playbook expects the user to have validated against.
+# This is bumped whenever a breaking change is introduced.
+# The value configured here needs to exist in `matrix_playbook_migration_breaking_changes` as well.
+matrix_playbook_migration_expected_version: "v2026.03.23.0"
+
+# A list of breaking changes, used to inform users what changed between their validated version and the expected version.
+matrix_playbook_migration_breaking_changes:
+  - version: "v2026.03.23.0"
+    summary: "Initial migration validation system"
+    changelog_url: "https://github.com/spantaleev/matrix-docker-ansible-deploy/blob/master/CHANGELOG.md#2026-03-22"
+
 # Controls if (`matrix_prometheus_nginxlog_exporter` -> `prometheus_nginxlog_exporter`) validation will run.
 matrix_playbook_migration_matrix_prometheus_nginxlog_exporter_migration_validation_enabled: true
 
diff --git a/roles/custom/matrix_playbook_migration/tasks/main.yml b/roles/custom/matrix_playbook_migration/tasks/main.yml
index 333380332..538521df1 100644
--- a/roles/custom/matrix_playbook_migration/tasks/main.yml
+++ b/roles/custom/matrix_playbook_migration/tasks/main.yml
@@ -1,9 +1,14 @@
-# SPDX-FileCopyrightText: 2022 - 2024 Slavi Pantaleev
+# SPDX-FileCopyrightText: 2022 - 2026 Slavi Pantaleev
 #
 # SPDX-License-Identifier: AGPL-3.0-or-later
 
 ---
 
+- tags:
+    - always
+  block:
+    - ansible.builtin.include_tasks: "{{ role_path }}/tasks/validate_migration_version.yml"
+
 - tags:
     - setup-all
     - install-all
diff --git a/roles/custom/matrix_playbook_migration/tasks/validate_migration_version.yml b/roles/custom/matrix_playbook_migration/tasks/validate_migration_version.yml
new file mode 100644
index 000000000..334f524cc
--- /dev/null
+++ b/roles/custom/matrix_playbook_migration/tasks/validate_migration_version.yml
@@ -0,0 +1,34 @@
+# SPDX-FileCopyrightText: 2026 Slavi Pantaleev
+#
+# SPDX-License-Identifier: AGPL-3.0-or-later
+
+---
+
+- name: Fail if migration version is not validated (first-time onboarding)
+  ansible.builtin.fail:
+    msg: >-
+      This playbook now uses a migration validation system to help you stay aware of breaking changes.
+
+      It appears that you haven't configured the `matrix_playbook_migration_validated_version` variable yet.
+
+      Please review the changelog (https://github.com/spantaleev/matrix-docker-ansible-deploy/blob/master/CHANGELOG.md)
+      and then add the following to your vars.yml file:
+
+      matrix_playbook_migration_validated_version: {{ matrix_playbook_migration_expected_version }}
+  when: "matrix_playbook_migration_validated_version == ''"
+
+- name: Fail if migration version is outdated
+  ansible.builtin.fail:
+    msg: |-
+      Your validated migration version ({{ matrix_playbook_migration_validated_version }}) is behind the expected version ({{ matrix_playbook_migration_expected_version }}).
+
+      The following breaking changes have been introduced since your last validation:
+
+      {% for item in matrix_playbook_migration_breaking_changes | selectattr('version', '>', matrix_playbook_migration_validated_version) | sort(attribute='version') %}
+      - {{ item.version }}: {{ item.summary }} ({{ item.changelog_url }})
+      {% endfor %}
+
+      After reviewing the above changes and adapting your setup, update your vars.yml:
+
+      matrix_playbook_migration_validated_version: "{{ matrix_playbook_migration_expected_version }}"
+  when: "matrix_playbook_migration_validated_version != '' and matrix_playbook_migration_validated_version < matrix_playbook_migration_expected_version"