diff --git a/README.md b/README.md
index 31fadc04..9941f5a6 100644
--- a/README.md
+++ b/README.md
@@ -57,48 +57,47 @@ If you ran in a Dev Docker environment, to view container logs: `docker compose
 
 ### [Getting Started](#getting-started)
 
-- [Quick Start (Linux/Mac)](docs/getting-started/quick-start-linux-mac.md)
-- [Single Compose Setup](docs/getting-started/single-compose-setup.md)
+- [Quick Start (Linux/Mac)](docs/01-getting-started/01-quick-start-linux-mac.md)
+- [Single Compose Setup](docs/01-getting-started/02-single-compose-setup.md)
 
 ### [Setup](#setup)
 
-- [Container Overview](docs/reference/container-setup/overview.md)
-- [Setup Options](docs/setup/setup-options.md)
-- [Single Server Example](docs/setup/single-server-example.md)
+- [Setup Options](docs/02-setup/01-setup-options.md)
+- [Single Server Example](docs/02-setup/02-single-server-example.md)
 
 ### [Production](#production)
 
-- [TLS/SSL Setup](docs/production/tls-ssl-setup.md)
-- [Backup Strategy](docs/production/backup-strategy.md)
-- [Multi-Tenancy](docs/production/multi-tenancy.md)
+- [TLS/SSL Setup](docs/03-production/01-tls-ssl-setup.md)
+- [Backup Strategy](docs/03-production/02-backup-strategy.md)
+- [Multi-Tenancy](docs/03-production/03-multi-tenancy.md)
 
 ### [Operations](#operations)
 
-- [Site Operations](docs/operations/site-operations.md)
+- [Site Operations](docs/04-operations/01-site-operations.md)
 
 ### [Development](#development)
 
-- [Development Guide](docs/development/development.md)
-- [Debugging](docs/development/debugging.md)
-- [Local Services Connection](docs/development/local-services-connection.md)
+- [Development Guide](docs/05-development/01-development.md)
+- [Debugging](docs/05-development/02-debugging.md)
+- [Local Services Connection](docs/05-development/03-local-services-connection.md)
 
 ### [Migration](#migration)
 
-- [Migrate from Multi-Image Setup](docs/migration/migrate-from-multi-image-setup.md)
+- [Migrate from Multi-Image Setup](docs/06-migration/01-migrate-from-multi-image-setup.md)
 
 ### [Troubleshooting](#troubleshooting)
 
-- [Troubleshoot Guide](docs/troubleshooting/troubleshoot.md)
-- [Windows Nginx Entrypoint Error](docs/troubleshooting/windows-nginx-entrypoint-error.md)
+- [Troubleshoot Guide](docs/07-troubleshooting/01-troubleshoot.md)
+- [Windows Nginx Entrypoint Error](docs/07-troubleshooting/02-windows-nginx-entrypoint-error.md)
 
 ### [Reference](#reference)
 
-- [Container Setup Overview](docs/reference/container-setup/overview.md)
-- [Build Setup](docs/reference/container-setup/build-setup.md)
-- [Start Setup](docs/reference/container-setup/start-setup.md)
-- [Environment Variables](docs/reference/container-setup/env-variables.md)
-- [Compose Overrides](docs/reference/container-setup/overrides.md)
-- [Build Version 10 Images](docs/reference/build-version-10-images.md)
+- [Container Setup Overview](docs/08-reference/container-setup/01-overview.md)
+- [Build Setup](docs/08-reference/container-setup/02-build-setup.md)
+- [Start Setup](docs/08-reference/container-setup/03-start-setup.md)
+- [Environment Variables](docs/08-reference/container-setup/04-env-variables.md)
+- [Compose Overrides](docs/08-reference/container-setup/05-overrides.md)
+- [Build Version 10 Images](docs/08-reference/01-build-version-10-images.md)
 
 # Contributing
 
diff --git a/docs/getting-started/quick-start-linux-mac.md b/docs/01-getting-started/01-quick-start-linux-mac.md
similarity index 100%
rename from docs/getting-started/quick-start-linux-mac.md
rename to docs/01-getting-started/01-quick-start-linux-mac.md
diff --git a/docs/getting-started/single-compose-setup.md b/docs/01-getting-started/02-single-compose-setup.md
similarity index 100%
rename from docs/getting-started/single-compose-setup.md
rename to docs/01-getting-started/02-single-compose-setup.md
diff --git a/docs/setup/setup-options.md b/docs/02-setup/01-setup-options.md
similarity index 92%
rename from docs/setup/setup-options.md
rename to docs/02-setup/01-setup-options.md
index 90dbe82d..34004fcf 100644
--- a/docs/setup/setup-options.md
+++ b/docs/02-setup/01-setup-options.md
@@ -17,7 +17,7 @@ Copy the example docker environment file to `.env`:
 cp example.env .env
 ```
 
-Note: To know more about environment variable [read here](../reference/container-setup/env-variables.md). Set the necessary variables in the `.env` file.
+Note: To know more about environment variable [read here](../08-reference/container-setup/04-env-variables.md). Set the necessary variables in the `.env` file.
 
 ## Generate docker-compose.yml for variety of setups
 
@@ -98,7 +98,7 @@ docker compose --project-name <project-name> -f ~/gitops/docker-compose.yml up -
 
 ## Create first site
 
-After starting containers, the first site needs to be created. Refer [site operations](../operations/site-operations.md#setup-new-site).
+After starting containers, the first site needs to be created. Refer [site operations](../04-operations/01-site-operations.md#setup-new-site).
 
 ## Updating Images
 
@@ -128,4 +128,4 @@ Note:
 - pull and stop container commands can be skipped if immutable image tags are used
 - `docker compose up -d` will pull new immutable tags if not found.
 
-To migrate sites refer [site operations](../operations/site-operations.md#migrate-site)
+To migrate sites refer [site operations](../04-operations/01-site-operations.md#migrate-site)
diff --git a/docs/setup/single-server-example.md b/docs/02-setup/02-single-server-example.md
similarity index 99%
rename from docs/setup/single-server-example.md
rename to docs/02-setup/02-single-server-example.md
index 8eea1f1f..b8bb42e4 100644
--- a/docs/setup/single-server-example.md
+++ b/docs/02-setup/02-single-server-example.md
@@ -285,4 +285,4 @@ docker compose --project-name custom-one-example -f ~/gitops/custom-one-example.
 
 ### Site operations
 
-Refer: [site operations](../operations/site-operations.md)
+Refer: [site operations](../04-operations/01-site-operations.md)
diff --git a/docs/production/tls-ssl-setup.md b/docs/03-production/01-tls-ssl-setup.md
similarity index 100%
rename from docs/production/tls-ssl-setup.md
rename to docs/03-production/01-tls-ssl-setup.md
diff --git a/docs/production/backup-strategy.md b/docs/03-production/02-backup-strategy.md
similarity index 100%
rename from docs/production/backup-strategy.md
rename to docs/03-production/02-backup-strategy.md
diff --git a/docs/production/multi-tenancy.md b/docs/03-production/03-multi-tenancy.md
similarity index 100%
rename from docs/production/multi-tenancy.md
rename to docs/03-production/03-multi-tenancy.md
diff --git a/docs/operations/site-operations.md b/docs/04-operations/01-site-operations.md
similarity index 95%
rename from docs/operations/site-operations.md
rename to docs/04-operations/01-site-operations.md
index f1c14af5..6822eadd 100644
--- a/docs/operations/site-operations.md
+++ b/docs/04-operations/01-site-operations.md
@@ -15,7 +15,7 @@ docker-compose exec backend bench new-site --mariadb-user-host-login-scope=% --d
 
 If you need to install some app, specify `--install-app`. To see all options, just run `bench new-site --help`.
 
-To create Postgres site (assuming you already use [Postgres compose override](../reference/container-setup/overrides.md)) you need have to do set `root_login` and `root_password` in common config before that:
+To create Postgres site (assuming you already use [Postgres compose override](../08-reference/container-setup/05-overrides.md)) you need have to do set `root_login` and `root_password` in common config before that:
 
 ```sh
 docker-compose exec backend bench set-config -g root_login <root-login>
diff --git a/docs/development/development.md b/docs/05-development/01-development.md
similarity index 100%
rename from docs/development/development.md
rename to docs/05-development/01-development.md
diff --git a/docs/development/debugging.md b/docs/05-development/02-debugging.md
similarity index 100%
rename from docs/development/debugging.md
rename to docs/05-development/02-debugging.md
diff --git a/docs/development/local-services-connection.md b/docs/05-development/03-local-services-connection.md
similarity index 100%
rename from docs/development/local-services-connection.md
rename to docs/05-development/03-local-services-connection.md
diff --git a/docs/migration/migrate-from-multi-image-setup.md b/docs/06-migration/01-migrate-from-multi-image-setup.md
similarity index 98%
rename from docs/migration/migrate-from-multi-image-setup.md
rename to docs/06-migration/01-migrate-from-multi-image-setup.md
index a2997d10..a1c8f746 100644
--- a/docs/migration/migrate-from-multi-image-setup.md
+++ b/docs/06-migration/01-migrate-from-multi-image-setup.md
@@ -6,7 +6,7 @@ Now you need to specify command and environment variables for following containe
 
 ### Frontend
 
-For `frontend` service to act as static assets frontend and reverse proxy, you need to pass `nginx-entrypoint.sh` as container `command` and `BACKEND` and `SOCKETIO` environment variables pointing `{host}:{port}` for gunicorn and websocket services. Check [environment variables](../reference/container-setup/env-variables.md)
+For `frontend` service to act as static assets frontend and reverse proxy, you need to pass `nginx-entrypoint.sh` as container `command` and `BACKEND` and `SOCKETIO` environment variables pointing `{host}:{port}` for gunicorn and websocket services. Check [environment variables](../08-reference/container-setup/04-env-variables.md)
 
 Now you only need to mount the `sites` volume at location `/home/frappe/frappe-bench/sites`. No need for `assets` volume and asset population script or steps.
 
diff --git a/docs/troubleshooting/troubleshoot.md b/docs/07-troubleshooting/01-troubleshoot.md
similarity index 100%
rename from docs/troubleshooting/troubleshoot.md
rename to docs/07-troubleshooting/01-troubleshoot.md
diff --git a/docs/troubleshooting/windows-nginx-entrypoint-error.md b/docs/07-troubleshooting/02-windows-nginx-entrypoint-error.md
similarity index 100%
rename from docs/troubleshooting/windows-nginx-entrypoint-error.md
rename to docs/07-troubleshooting/02-windows-nginx-entrypoint-error.md
diff --git a/docs/reference/build-version-10-images.md b/docs/08-reference/01-build-version-10-images.md
similarity index 100%
rename from docs/reference/build-version-10-images.md
rename to docs/08-reference/01-build-version-10-images.md
diff --git a/docs/reference/container-setup/overview.md b/docs/08-reference/container-setup/01-overview.md
similarity index 96%
rename from docs/reference/container-setup/overview.md
rename to docs/08-reference/container-setup/01-overview.md
index f79d2287..eeb493cc 100644
--- a/docs/reference/container-setup/overview.md
+++ b/docs/08-reference/container-setup/01-overview.md
@@ -40,8 +40,8 @@ Once images are built, containers are orchestrated using a [compose file](https:
 
 Additional functionality can be added using [overrides](https://docs.docker.com/compose/extends/). These files modify existing services or add new ones without changing the main `compose.yaml`.
 
-Example: The main compose file has no database service, but `compose.mariadb.yaml` adds MariaDB. See [overrides.md](overrides.md) for the complete list of available overrides and how to use them.
+Example: The main compose file has no database service, but `compose.mariadb.yaml` adds MariaDB. See [overrides.md](05-overrides.md) for the complete list of available overrides and how to use them.
 
 ---
 
-**Next:** [Build Setup →](build-setup.md)
+**Next:** [Build Setup →](02-build-setup.md)
diff --git a/docs/reference/container-setup/build-setup.md b/docs/08-reference/container-setup/02-build-setup.md
similarity index 95%
rename from docs/reference/container-setup/build-setup.md
rename to docs/08-reference/container-setup/02-build-setup.md
index 7d78d07e..84402361 100644
--- a/docs/reference/container-setup/build-setup.md
+++ b/docs/08-reference/container-setup/02-build-setup.md
@@ -95,7 +95,7 @@ The compose file requires several environment variables. You can either export t
 cp example.env custom.env
 ```
 
-Edit `custom.env` to customize variables for your setup. The template includes common variables, but you can add, modify, or remove any as needed. See [env-variables.md](env-variables.md) for detailed descriptions of all available variables.
+Edit `custom.env` to customize variables for your setup. The template includes common variables, but you can add, modify, or remove any as needed. See [env-variables.md](04-env-variables.md) for detailed descriptions of all available variables.
 
 # Creating the final compose file
 
@@ -116,6 +116,6 @@ This generates `compose.custom.yaml`, which you'll use to start all containers.
 
 ---
 
-**Next:** [Start Setup →](start-setup.md)
+**Next:** [Start Setup →](03-start-setup.md)
 
-**Back:** [Container Overview ←](overview.md)
+**Back:** [Container Overview ←](01-overview.md)
diff --git a/docs/reference/container-setup/start-setup.md b/docs/08-reference/container-setup/03-start-setup.md
similarity index 97%
rename from docs/reference/container-setup/start-setup.md
rename to docs/08-reference/container-setup/03-start-setup.md
index 8c453cf2..e19df758 100644
--- a/docs/reference/container-setup/start-setup.md
+++ b/docs/08-reference/container-setup/03-start-setup.md
@@ -39,4 +39,4 @@ Replace `<sitename>` with your desired site name.
 
 ---
 
-**Back:** [Build Setup →](build-setup.md)
+**Back:** [Build Setup →](02-build-setup.md)
diff --git a/docs/reference/container-setup/env-variables.md b/docs/08-reference/container-setup/04-env-variables.md
similarity index 100%
rename from docs/reference/container-setup/env-variables.md
rename to docs/08-reference/container-setup/04-env-variables.md
diff --git a/docs/reference/container-setup/overrides.md b/docs/08-reference/container-setup/05-overrides.md
similarity index 100%
rename from docs/reference/container-setup/overrides.md
rename to docs/08-reference/container-setup/05-overrides.md