diff --git a/Dockerfile.debug b/Dockerfile.debug
index 78c3613e..7ffcf63c 100644
--- a/Dockerfile.debug
+++ b/Dockerfile.debug
@@ -72,4 +72,4 @@ HEALTHCHECK --interval=5m --start-period=1m --timeout=30s --retries=3 \
 
 RUN [ "cross-build-end" ]
 
-CMD DEBUG=1 ./entry.sh
+CMD DEBUG=1 ./entry.sh || while true; do echo 'Supervisor runtime exited - waiting for changes'; sleep 100; done;
diff --git a/package-lock.json b/package-lock.json
index fa7389b7..2c83f0a4 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -6303,9 +6303,9 @@
       }
     },
     "livepush": {
-      "version": "1.2.1",
-      "resolved": "https://registry.npmjs.org/livepush/-/livepush-1.2.1.tgz",
-      "integrity": "sha512-6BD16S8EtyVsNqI5PHI/MRiho1LhkYR9Gjy2AXWm3S/cssV0TlVJpyhz1nMWxCDGjbJAWjcYwbvSAeBua7RUhA==",
+      "version": "1.2.4",
+      "resolved": "https://registry.npmjs.org/livepush/-/livepush-1.2.4.tgz",
+      "integrity": "sha512-AKGlJ+QuelyDoOV0cbGfeskLf2RaYIcHnKogfircvTl9//BNDrGVhrcO6bN3kcVaJnYKnvXwXOtGOyrsl6wI9A==",
       "dev": true,
       "requires": {
         "bluebird": "^3.5.1",
diff --git a/package.json b/package.json
index ad411ba1..988e16ab 100644
--- a/package.json
+++ b/package.json
@@ -73,7 +73,7 @@
     "json-mask": "^0.3.8",
     "knex": "~0.15.2",
     "lint-staged": "^8.1.0",
-    "livepush": "^1.2.1",
+    "livepush": "^1.2.4",
     "lockfile": "^1.0.1",
     "lodash": "^4.17.5",
     "log-timestamp": "^0.1.2",
diff --git a/sync-debug.js b/sync-debug.js
index 64513050..f7de4a4e 100755
--- a/sync-debug.js
+++ b/sync-debug.js
@@ -50,9 +50,20 @@ function extractMessage(msgBuf) {
 	return;
 }
 
+let changedFiles = [];
+let deletedFiles = [];
+
+const performLivepush = _.debounce(async livepush => {
+	await livepush.performLivepush(changedFiles, deletedFiles);
+	changedFiles = [];
+	deletedFiles = [];
+}, 1000);
+
 (async () => {
+	console.log('Starting up...');
 	// Get the supervisor container id
 	const container = await docker.getContainer('resin_supervisor').inspect();
+	console.log('Supervisor container id: ', container.Id);
 	const containerId = container.Id;
 	const image = container.Image;
 
@@ -67,20 +78,22 @@ function extractMessage(msgBuf) {
 		docker,
 	);
 
-	// TODO: Debounce these calls
 	chokidar
 		.watch('.', {
 			ignored: /((^|[\/\\])\..|node_modules.*)/,
-			ignoreInitial: true,
+			ignoreInitial: false,
 		})
 		.on('add', path => {
-			livepush.performLivepush([path], []);
+			changedFiles.push(path);
+			performLivepush(livepush);
 		})
 		.on('change', path => {
-			livepush.performLivepush([path], []);
+			changedFiles.push(path);
+			performLivepush(livepush);
 		})
 		.on('unlink', path => {
-			livepush.performLivepush([], [path]);
+			deletedFiles.push(path);
+			performLivepush(livepush);
 		});
 
 	livepush.on('commandExecute', ({ command }) => {