diff --git a/.devcontainer.json b/.devcontainer.json
deleted file mode 100644
index 79ad867c5028a..0000000000000
--- a/.devcontainer.json
+++ /dev/null
@@ -1,9 +0,0 @@
-{
-    "name": "Dev Container Definition - AWS CDK",
-    "image": "jsii/superchain:1-buster-slim",
-    "postCreateCommand": "yarn build --skip-test --no-bail --skip-prereqs --skip-compat",
-    "extensions": [
-        "dbaeumer.vscode-eslint@2.1.5"
-    ],
-    "remoteUser": "superchain"
-}
diff --git a/.devcontainer/Dockerfile b/.devcontainer/Dockerfile
new file mode 100644
index 0000000000000..84415387968ea
--- /dev/null
+++ b/.devcontainer/Dockerfile
@@ -0,0 +1,19 @@
+FROM jsii/superchain:1-buster-slim
+
+USER root
+
+# Change uid/guid of superchain so it can work with the docker-in-docker feature
+RUN groupmod --gid 1000 superchain \
+    && usermod --uid 1000 --gid 1000 superchain \
+    && chown -R 1000:1000 /home/superchain
+
+USER superchain
+
+# Setup oh-my-zsh
+RUN sudo apt-get update && export DEBIAN_FRONTEND=noninteractive \
+    && sudo apt-get -y install --no-install-recommends zsh vim \
+    && sudo rm -rf /var/lib/apt/lists/* \
+    && sudo chsh -s $(which zsh) $(whoami)
+RUN sh -c "$(curl -fsSL https://raw.githubusercontent.com/ohmyzsh/ohmyzsh/master/tools/install.sh)" "" --unattended \
+    # Required, otherwise shell is extermly slow due the size of the aws-cdk
+    && sudo sh -c 'echo "[oh-my-zsh]\n        hide-dirty = 1" > /etc/gitconfig'
diff --git a/.devcontainer/devcontainer.json b/.devcontainer/devcontainer.json
new file mode 100644
index 0000000000000..98e6bf94be412
--- /dev/null
+++ b/.devcontainer/devcontainer.json
@@ -0,0 +1,21 @@
+{
+  "name": "aws-cdk",
+  "build": {
+    "dockerfile": "Dockerfile"
+  },
+
+  "customizations": {
+    "vscode": {
+      "extensions": ["dbaeumer.vscode-eslint"]
+    }
+  },
+
+  "postCreateCommand": "yarn install",
+  "remoteUser": "superchain",
+  "features": {
+    "docker-in-docker": {
+      "version": "latest",
+      "moby": true
+    }
+  }
+}
diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index ec8de994ef2b7..2b0de4e77dccc 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -14,6 +14,8 @@ This document describes how to set up a development environment and submit your
 let us know if it's not up-to-date (even better, submit a PR with your  corrections ;-)).
 
 - [Getting Started](#getting-started)
+  - [Local setup](#setup)
+  - [Dev Container](#dev-container)
 - [Pull Requests](#pull-requests)
   - [Step 1: Find something to work on](#step-1-find-something-to-work-on)
   - [Step 2: Design (optional)](#step-2-design)
@@ -23,7 +25,7 @@ let us know if it's not up-to-date (even better, submit a PR with your  correcti
 - [Breaking Changes](#breaking-changes)
 - [Documentation](#documentation)
   - [Rosetta](#rosetta)
-- [Tools](#tools)
+- [Tools](#tools-advanced)
   - [Linters](#linters)
   - [cfn2ts](#cfn2ts)
   - [scripts/foreach.sh](#scriptsforeachsh)
@@ -147,7 +149,14 @@ docker$ exit
 
 The `dist/` folder within each module contains the packaged up language artifacts.
 
-## Gitpod (Alternative)
+### Dev Container
+
+The AWS CDK provides a VS Code Dev Container with all dependencies pre-installed.
+Please follow the [setup instructions](https://code.visualstudio.com/docs/remote/containers-tutorial) to configure VS Code.
+
+With VS Code setup, you will be prompted to open the `aws-cdk` repo in a Dev Container, or you can choos "Dev Containers: Reopen in Container" from the VS Code command palette.
+
+### Gitpod (Alternative)
 
 You may also set up your local development environment using [Gitpod](http://gitpod.io) -
 a service that allows you to spin up an in-browser Visual Studio Code-compatible editor,