diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index 9a306d126e73..4ff8e29f6262 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -25,6 +25,12 @@ repos:
     hooks:
       - id: identity
       - id: check-hooks-apply
+  - repo: https://github.com/thlorenz/doctoc.git
+    rev: v2.2.0
+    hooks:
+      - id: doctoc
+        name: Add TOC for Markdown files
+        files: ^CONTRIBUTING\.md$|^INSTALL\.md$|^README\.md$
   - repo: https://github.com/oxipng/oxipng
     rev: v9.1.5
     hooks:
@@ -41,6 +47,11 @@ repos:
   - repo: https://github.com/Lucas-C/pre-commit-hooks
     rev: v1.5.5
     hooks:
+      - id: chmod
+        name: set file permissions
+        args: ['644']
+        files: \.md$
+        stages: [manual]
       - id: insert-license
         name: add license for all Markdown files
         files: \.md$
@@ -117,14 +128,6 @@ repos:
         args: [--config=.github/linters/.markdown-lint.yml]
         types: [markdown]
         files: \.(md|mdown|markdown)$
-  - repo: https://github.com/Lucas-C/pre-commit-hooks
-    rev: v1.5.5
-    hooks:
-      - id: chmod
-        name: set file permissions
-        args: ['644']
-        files: \.md$
-        stages: [manual]
   - repo: https://github.com/adrienverge/yamllint
     rev: v1.37.1
     hooks:
diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index 57b7a716cd4a..f0678ed76498 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -21,6 +21,24 @@
 
 ## Summary
 
+<!-- START doctoc generated TOC please keep comment here to allow auto update -->
+<!-- DON'T EDIT THIS SECTION, INSTEAD RE-RUN doctoc TO UPDATE -->
+
+- [Summary](#summary)
+- [Bug fixes](#bug-fixes)
+- [Developing new features](#developing-new-features)
+- [PendingReleaseNotes file](#pendingreleasenotes-file)
+- [Fork the code](#fork-the-code)
+- [Making changes](#making-changes)
+- [Rebase `feature_x` to include updates from `upstream/main`](#rebase-feature_x-to-include-updates-from-upstreammain)
+- [Make a GitHub Pull Request to contribute your changes](#make-a-github-pull-request-to-contribute-your-changes)
+- [Cleaning up after a successful pull request](#cleaning-up-after-a-successful-pull-request)
+- [Release Principles](#release-principles)
+
+<!-- END doctoc generated TOC please keep comment here to allow auto update -->
+
+## Summary
+
 This document covers how to contribute to the ACS project. ACS uses GitHub PRs to manage code contributions.
 These instructions assume you have a GitHub.com account, so if you don't have one you will have to create one. Your proposed code changes will be published to your own fork of the ACS project, and you will submit a Pull Request for your changes to be added.
 
diff --git a/INSTALL.md b/INSTALL.md
index 0619b97f21c1..52f109b0a411 100644
--- a/INSTALL.md
+++ b/INSTALL.md
@@ -26,9 +26,21 @@ or the developer [wiki](https://cwiki.apache.org/confluence/display/CLOUDSTACK/H
 Apache CloudStack developers use various platforms for development, this guide
 was tested against a CentOS 7 x86_64 setup.
 
-* [Setting up development environment](https://cwiki.apache.org/confluence/display/CLOUDSTACK/Setting+up+CloudStack+Development+Environment) for Apache CloudStack.
-* [Building](https://cwiki.apache.org/confluence/display/CLOUDSTACK/How+to+build+CloudStack) Apache CloudStack.
-* [Appliance based development](https://github.com/rhtyd/monkeybox)
+<!-- START doctoc generated TOC please keep comment here to allow auto update -->
+<!-- DON'T EDIT THIS SECTION, INSTEAD RE-RUN doctoc TO UPDATE -->
+
+- [Setting up Development Environment](#setting-up-development-environment)
+  - [Using jenv and/or pyenv for Version Management](#using-jenv-andor-pyenv-for-version-management)
+- [Getting the Source Code](#getting-the-source-code)
+- [Building](#building)
+- [To bring up CloudStack UI](#to-bring-up-cloudstack-ui)
+- [Building with non-redistributable plugins](#building-with-non-redistributable-plugins)
+- [Packaging and Installation](#packaging-and-installation)
+  - [Debian/Ubuntu](#debianubuntu)
+  - [RHEL/CentOS](#rhelcentos)
+- [Notes](#notes)
+
+<!-- END doctoc generated TOC please keep comment here to allow auto update -->
 
 ## Setting up Development Environment
 
diff --git a/README.md b/README.md
index a24131958a2c..a5aacb49f6b5 100644
--- a/README.md
+++ b/README.md
@@ -31,6 +31,24 @@
 
 [![Apache CloudStack](tools/logo/apache_cloudstack.png)](https://cloudstack.apache.org/)
 
+<!-- START doctoc generated TOC please keep comment here to allow auto update -->
+<!-- DON'T EDIT THIS SECTION, INSTEAD RE-RUN doctoc TO UPDATE -->
+
+- [Who Uses CloudStack?](#who-uses-cloudstack)
+- [Demo](#demo)
+- [Getting Started](#getting-started)
+- [Getting Source Repository](#getting-source-repository)
+- [Documentation](#documentation)
+- [News and Events](#news-and-events)
+- [Getting Involved and Contributing](#getting-involved-and-contributing)
+- [Reporting Security Vulnerabilities](#reporting-security-vulnerabilities)
+- [License](#license)
+- [Notice of Cryptographic Software](#notice-of-cryptographic-software)
+- [Star History](#star-history)
+- [Contributors](#contributors)
+
+<!-- END doctoc generated TOC please keep comment here to allow auto update -->
+
 Apache CloudStack is open source software designed to deploy and manage large
 networks of virtual machines, as a highly available, highly scalable
 Infrastructure as a Service (IaaS) cloud computing platform. CloudStack is used