diff --git a/.vscode/launch.json b/.vscode/launch.json
new file mode 100644
index 00000000..f5bc52f8
--- /dev/null
+++ b/.vscode/launch.json
@@ -0,0 +1,20 @@
+{
+    "version": "0.2.0",
+    "configurations": [
+        {
+            "type": "node",
+            "request": "attach",
+            "name": "Attach to remote",
+            "address": "127.0.0.1",
+            "port": 9229,
+            "cwd": "${workspaceRoot}",
+            "program": "${workspaceRoot}/src/app.ts",
+            "outFiles": [
+              "${workspaceRoot}/dist/bundle.js"
+            ],
+            "sourceMaps": true,
+            "localRoot": "${workspaceFolder}",
+            "remoteRoot": "/usr/src/app"
+        }
+    ]
+} 
diff --git a/README.md b/README.md
index dd504590..7f7c8de1 100644
--- a/README.md
+++ b/README.md
@@ -101,6 +101,12 @@ and sync any relevant file changes to the running supervisor
 container. It will then decide if the container should be
 restarted, or let nodemon handle the changes.
 
+### Debugging
+
+Using live push the supervisor starts with remote debugging enabled via the --inspect flag. Use Chrome dev tools, or your IDE to [start a debugging session](https://nodejs.org/en/docs/guides/debugging-getting-started/#inspector-clients).
+
+Connect your debugger to `<device-local-ip>:9229`
+
 ### Using balenaOS-in-container
 
 This process will allow you to run a development instance of the supervisor on your local computer. It is not recommended for production scenarios, but allows someone developing on the supervisor to test changes quickly.
diff --git a/entry.sh b/entry.sh
index 0e242e8d..70813223 100755
--- a/entry.sh
+++ b/entry.sh
@@ -58,7 +58,7 @@ modprobe ip6_tables || true
 
 if [ "${LIVEPUSH}" = "1" ]; then
 	exec npx nodemon --watch src --watch typings --ignore tests -e js,ts,json \
-		 --exec node -r ts-node/register/transpile-only src/app.ts
+		 --exec node -r ts-node/register/transpile-only --inspect=0.0.0.0 src/app.ts
 else
 	exec node /usr/src/app/dist/app.js
 fi
diff --git a/tsconfig.json b/tsconfig.json
index 1ec3cc9e..dc5481b6 100644
--- a/tsconfig.json
+++ b/tsconfig.json
@@ -6,7 +6,7 @@
 		"strictFunctionTypes": false,
 		"strictPropertyInitialization": false,
 		"preserveConstEnums": true,
-		"inlineSourceMap": true,
+		"sourceMap": true,
 		"outDir": "./build/",
 		"skipLibCheck": true,
 		"lib": ["es2019"],
diff --git a/webpack.config.js b/webpack.config.js
index e086a38c..5d5e14eb 100644
--- a/webpack.config.js
+++ b/webpack.config.js
@@ -70,11 +70,12 @@ console.log('Using the following dependencies as external:', externalModules);
 module.exports = function (env) {
 	return {
 		mode: env == null || !env.noOptimize ? 'production' : 'development',
-		devtool: 'none',
+		devtool: 'source-map',
 		entry: './src/app.ts',
 		output: {
 			filename: 'app.js',
 			path: path.resolve(__dirname, 'dist'),
+			devtoolModuleFilenameTemplate: '[absolute-resource-path]',
 		},
 		resolve: {
 			extensions: ['.js', '.ts', '.json'],