diff --git a/plugins/.empty b/plugins/.empty
new file mode 100644
index 0000000000000..e69de29bb2d1d
diff --git a/src/cli/cluster/cluster_manager.ts b/src/cli/cluster/cluster_manager.ts
index e1f56a2f267fa..3d81185e8a313 100644
--- a/src/cli/cluster/cluster_manager.ts
+++ b/src/cli/cluster/cluster_manager.ts
@@ -19,6 +19,7 @@
 
 import { resolve } from 'path';
 import { format as formatUrl } from 'url';
+import Fs from 'fs';
 
 import opn from 'opn';
 import { REPO_ROOT } from '@kbn/utils';
@@ -233,6 +234,14 @@ export class ClusterManager {
       )
     );
 
+    for (const watchPath of watchPaths) {
+      if (!Fs.existsSync(fromRoot(watchPath))) {
+        throw new Error(
+          `A watch directory [${watchPath}] does not exist, which will cause chokidar to fail. Either make sure the directory exists or remove it as a watch source in the ClusterManger`
+        );
+      }
+    }
+
     const ignorePaths = [
       /[\\\/](\..*|node_modules|bower_components|target|public|__[a-z0-9_]+__|coverage)([\\\/]|$)/,
       /\.test\.(js|tsx?)$/,