diff --git a/packages/webpack5/__tests__/configuration/__snapshots__/angular.spec.ts.snap b/packages/webpack5/__tests__/configuration/__snapshots__/angular.spec.ts.snap
index c2f2a5a1d..d89856404 100644
--- a/packages/webpack5/__tests__/configuration/__snapshots__/angular.spec.ts.snap
+++ b/packages/webpack5/__tests__/configuration/__snapshots__/angular.spec.ts.snap
@@ -123,7 +123,12 @@ exports[`angular configuration for android 1`] = `
       },
       /* config.module.rule('css') */
       {
-        test: /app(\\\\.\\\\w+)?\\\\.css$/,
+        test: /\\\\.css$/,
+        include: [
+          '__jest__/src/app.css',
+          '__jest__/src/app.android.css',
+          /node_modules/
+        ],
         use: [
           /* config.module.rule('css').use('apply-css-loader') */
           {
@@ -148,7 +153,12 @@ exports[`angular configuration for android 1`] = `
       },
       /* config.module.rule('scss') */
       {
-        test: /app(\\\\.\\\\w+)?\\\\.scss$/,
+        test: /\\\\.scss$/,
+        include: [
+          '__jest__/src/app.scss',
+          '__jest__/src/app.android.scss',
+          /node_modules/
+        ],
         use: [
           /* config.module.rule('scss').use('apply-css-loader') */
           {
@@ -206,7 +216,9 @@ exports[`angular configuration for android 1`] = `
       {
         test: /\\\\.css$/,
         exclude: [
-          /app(\\\\.\\\\w+)?\\\\.css$/
+          '__jest__/src/app.css',
+          '__jest__/src/app.android.css',
+          /node_modules/
         ],
         use: [
           /* config.module.rule('css|component').use('raw-loader') */
@@ -219,7 +231,9 @@ exports[`angular configuration for android 1`] = `
       {
         test: /\\\\.scss$/,
         exclude: [
-          /app(\\\\.\\\\w+)?\\\\.scss$/
+          '__jest__/src/app.css',
+          '__jest__/src/app.android.css',
+          /node_modules/
         ],
         use: [
           /* config.module.rule('scss|component').use('raw-loader') */
@@ -494,7 +508,12 @@ exports[`angular configuration for ios 1`] = `
       },
       /* config.module.rule('css') */
       {
-        test: /app(\\\\.\\\\w+)?\\\\.css$/,
+        test: /\\\\.css$/,
+        include: [
+          '__jest__/src/app.css',
+          '__jest__/src/app.ios.css',
+          /node_modules/
+        ],
         use: [
           /* config.module.rule('css').use('apply-css-loader') */
           {
@@ -519,7 +538,12 @@ exports[`angular configuration for ios 1`] = `
       },
       /* config.module.rule('scss') */
       {
-        test: /app(\\\\.\\\\w+)?\\\\.scss$/,
+        test: /\\\\.scss$/,
+        include: [
+          '__jest__/src/app.scss',
+          '__jest__/src/app.ios.scss',
+          /node_modules/
+        ],
         use: [
           /* config.module.rule('scss').use('apply-css-loader') */
           {
@@ -577,7 +601,9 @@ exports[`angular configuration for ios 1`] = `
       {
         test: /\\\\.css$/,
         exclude: [
-          /app(\\\\.\\\\w+)?\\\\.css$/
+          '__jest__/src/app.css',
+          '__jest__/src/app.ios.css',
+          /node_modules/
         ],
         use: [
           /* config.module.rule('css|component').use('raw-loader') */
@@ -590,7 +616,9 @@ exports[`angular configuration for ios 1`] = `
       {
         test: /\\\\.scss$/,
         exclude: [
-          /app(\\\\.\\\\w+)?\\\\.scss$/
+          '__jest__/src/app.css',
+          '__jest__/src/app.ios.css',
+          /node_modules/
         ],
         use: [
           /* config.module.rule('scss|component').use('raw-loader') */
diff --git a/packages/webpack5/__tests__/configuration/__snapshots__/base.spec.ts.snap b/packages/webpack5/__tests__/configuration/__snapshots__/base.spec.ts.snap
index 584b94a3c..801d934ce 100644
--- a/packages/webpack5/__tests__/configuration/__snapshots__/base.spec.ts.snap
+++ b/packages/webpack5/__tests__/configuration/__snapshots__/base.spec.ts.snap
@@ -223,6 +223,7 @@ exports[`base configuration for android 1`] = `
     /* config.plugin('ForkTsCheckerWebpackPlugin') */
     new ForkTsCheckerWebpackPlugin(
       {
+        async: false,
         typescript: {
           memoryLimit: 4096
         }
@@ -530,6 +531,7 @@ exports[`base configuration for ios 1`] = `
     /* config.plugin('ForkTsCheckerWebpackPlugin') */
     new ForkTsCheckerWebpackPlugin(
       {
+        async: false,
         typescript: {
           memoryLimit: 4096
         }
diff --git a/packages/webpack5/__tests__/configuration/__snapshots__/javascript.spec.ts.snap b/packages/webpack5/__tests__/configuration/__snapshots__/javascript.spec.ts.snap
index 4135f11db..c4fc4fcf6 100644
--- a/packages/webpack5/__tests__/configuration/__snapshots__/javascript.spec.ts.snap
+++ b/packages/webpack5/__tests__/configuration/__snapshots__/javascript.spec.ts.snap
@@ -240,6 +240,7 @@ exports[`javascript configuration for android 1`] = `
     /* config.plugin('ForkTsCheckerWebpackPlugin') */
     new ForkTsCheckerWebpackPlugin(
       {
+        async: false,
         typescript: {
           memoryLimit: 4096
         }
@@ -320,10 +321,10 @@ exports[`javascript configuration for android 1`] = `
   entry: {
     bundle: [
       '@nativescript/core/globals/index.js',
+      '__jest__/src/__@nativescript_webpack_virtual_entry_javascript__',
       '__jest__/src/app.js',
       '@nativescript/core/ui/frame',
-      '@nativescript/core/ui/frame/activity',
-      '__jest__/src/__@nativescript_webpack_virtual_entry_javascript__'
+      '@nativescript/core/ui/frame/activity'
     ]
   }
 }"
@@ -569,6 +570,7 @@ exports[`javascript configuration for ios 1`] = `
     /* config.plugin('ForkTsCheckerWebpackPlugin') */
     new ForkTsCheckerWebpackPlugin(
       {
+        async: false,
         typescript: {
           memoryLimit: 4096
         }
@@ -649,8 +651,8 @@ exports[`javascript configuration for ios 1`] = `
   entry: {
     bundle: [
       '@nativescript/core/globals/index.js',
-      '__jest__/src/app.js',
-      '__jest__/src/__@nativescript_webpack_virtual_entry_javascript__'
+      '__jest__/src/__@nativescript_webpack_virtual_entry_javascript__',
+      '__jest__/src/app.js'
     ],
     'tns_modules/inspector_modules': [
       '@nativescript/core/inspector_modules'
diff --git a/packages/webpack5/__tests__/configuration/__snapshots__/react.spec.ts.snap b/packages/webpack5/__tests__/configuration/__snapshots__/react.spec.ts.snap
index e1e15a5f2..2d35a4f8a 100644
--- a/packages/webpack5/__tests__/configuration/__snapshots__/react.spec.ts.snap
+++ b/packages/webpack5/__tests__/configuration/__snapshots__/react.spec.ts.snap
@@ -238,6 +238,7 @@ exports[`react configuration > android > adds ReactRefreshWebpackPlugin when HMR
     /* config.plugin('ForkTsCheckerWebpackPlugin') */
     new ForkTsCheckerWebpackPlugin(
       {
+        async: false,
         typescript: {
           memoryLimit: 4096
         }
@@ -556,6 +557,7 @@ exports[`react configuration > android > base config 1`] = `
     /* config.plugin('ForkTsCheckerWebpackPlugin') */
     new ForkTsCheckerWebpackPlugin(
       {
+        async: false,
         typescript: {
           memoryLimit: 4096
         }
@@ -874,6 +876,7 @@ exports[`react configuration > ios > adds ReactRefreshWebpackPlugin when HMR ena
     /* config.plugin('ForkTsCheckerWebpackPlugin') */
     new ForkTsCheckerWebpackPlugin(
       {
+        async: false,
         typescript: {
           memoryLimit: 4096
         }
@@ -1193,6 +1196,7 @@ exports[`react configuration > ios > base config 1`] = `
     /* config.plugin('ForkTsCheckerWebpackPlugin') */
     new ForkTsCheckerWebpackPlugin(
       {
+        async: false,
         typescript: {
           memoryLimit: 4096
         }
diff --git a/packages/webpack5/__tests__/configuration/__snapshots__/svelte.spec.ts.snap b/packages/webpack5/__tests__/configuration/__snapshots__/svelte.spec.ts.snap
index 2066d45fa..aeb3abb79 100644
--- a/packages/webpack5/__tests__/configuration/__snapshots__/svelte.spec.ts.snap
+++ b/packages/webpack5/__tests__/configuration/__snapshots__/svelte.spec.ts.snap
@@ -248,6 +248,7 @@ exports[`svelte configuration for android 1`] = `
     /* config.plugin('ForkTsCheckerWebpackPlugin') */
     new ForkTsCheckerWebpackPlugin(
       {
+        async: false,
         typescript: {
           memoryLimit: 4096
         }
@@ -574,6 +575,7 @@ exports[`svelte configuration for ios 1`] = `
     /* config.plugin('ForkTsCheckerWebpackPlugin') */
     new ForkTsCheckerWebpackPlugin(
       {
+        async: false,
         typescript: {
           memoryLimit: 4096
         }
diff --git a/packages/webpack5/__tests__/configuration/__snapshots__/typescript.spec.ts.snap b/packages/webpack5/__tests__/configuration/__snapshots__/typescript.spec.ts.snap
index b63248635..1b820ec3c 100644
--- a/packages/webpack5/__tests__/configuration/__snapshots__/typescript.spec.ts.snap
+++ b/packages/webpack5/__tests__/configuration/__snapshots__/typescript.spec.ts.snap
@@ -240,6 +240,7 @@ exports[`typescript configuration for android 1`] = `
     /* config.plugin('ForkTsCheckerWebpackPlugin') */
     new ForkTsCheckerWebpackPlugin(
       {
+        async: false,
         typescript: {
           memoryLimit: 4096
         }
@@ -320,10 +321,10 @@ exports[`typescript configuration for android 1`] = `
   entry: {
     bundle: [
       '@nativescript/core/globals/index.js',
+      '__jest__/src/__@nativescript_webpack_virtual_entry_typescript__',
       '__jest__/src/app.js',
       '@nativescript/core/ui/frame',
-      '@nativescript/core/ui/frame/activity',
-      '__jest__/src/__@nativescript_webpack_virtual_entry_typescript__'
+      '@nativescript/core/ui/frame/activity'
     ]
   }
 }"
@@ -569,6 +570,7 @@ exports[`typescript configuration for ios 1`] = `
     /* config.plugin('ForkTsCheckerWebpackPlugin') */
     new ForkTsCheckerWebpackPlugin(
       {
+        async: false,
         typescript: {
           memoryLimit: 4096
         }
@@ -649,8 +651,8 @@ exports[`typescript configuration for ios 1`] = `
   entry: {
     bundle: [
       '@nativescript/core/globals/index.js',
-      '__jest__/src/app.js',
-      '__jest__/src/__@nativescript_webpack_virtual_entry_typescript__'
+      '__jest__/src/__@nativescript_webpack_virtual_entry_typescript__',
+      '__jest__/src/app.js'
     ],
     'tns_modules/inspector_modules': [
       '@nativescript/core/inspector_modules'
diff --git a/packages/webpack5/__tests__/configuration/__snapshots__/vue.spec.ts.snap b/packages/webpack5/__tests__/configuration/__snapshots__/vue.spec.ts.snap
index 650a40dee..97e6dd9de 100644
--- a/packages/webpack5/__tests__/configuration/__snapshots__/vue.spec.ts.snap
+++ b/packages/webpack5/__tests__/configuration/__snapshots__/vue.spec.ts.snap
@@ -257,6 +257,7 @@ exports[`vue configuration for android 1`] = `
     /* config.plugin('ForkTsCheckerWebpackPlugin') */
     new ForkTsCheckerWebpackPlugin(
       {
+        async: false,
         typescript: {
           memoryLimit: 4096,
           extensions: {
@@ -598,6 +599,7 @@ exports[`vue configuration for ios 1`] = `
     /* config.plugin('ForkTsCheckerWebpackPlugin') */
     new ForkTsCheckerWebpackPlugin(
       {
+        async: false,
         typescript: {
           memoryLimit: 4096,
           extensions: {
diff --git a/packages/webpack5/src/bin/index.ts b/packages/webpack5/src/bin/index.ts
index 45697829c..7b63ef183 100644
--- a/packages/webpack5/src/bin/index.ts
+++ b/packages/webpack5/src/bin/index.ts
@@ -56,6 +56,8 @@ program
 			env['env'] = options.env;
 		}
 
+		env['watch'] = options.watch;
+
 		const configPath = (() => {
 			if (options.config) {
 				return path.resolve(options.config);
diff --git a/packages/webpack5/src/configuration/angular.ts b/packages/webpack5/src/configuration/angular.ts
index 2cdafcae2..ab91d163a 100644
--- a/packages/webpack5/src/configuration/angular.ts
+++ b/packages/webpack5/src/configuration/angular.ts
@@ -186,7 +186,7 @@ export default function (config: Config, env: IWebpackEnv = _env): Config {
 				paths.indexOf('@nativescript/core/globals/index.js')
 			] = polyfillsPath;
 
-			// replace paths with the update paths
+			// replace paths with the updated paths
 			config.entry('bundle').clear().merge(paths);
 		}
 	}
diff --git a/packages/webpack5/src/configuration/base.ts b/packages/webpack5/src/configuration/base.ts
index 3eea33103..90c7f0a6a 100644
--- a/packages/webpack5/src/configuration/base.ts
+++ b/packages/webpack5/src/configuration/base.ts
@@ -233,11 +233,7 @@ export default function (config: Config, env: IWebpackEnv = _env): Config {
 			.plugin('ForkTsCheckerWebpackPlugin')
 			.use(ForkTsCheckerWebpackPlugin, [
 				{
-					// If we use "async" errors compiling typescript will be ignored by
-					// WebPack (we will send the "compilation" message back to the CLI,
-					// and the process exit code will be zero), therefore we will end
-					// up with a broken build
-					async: false,
+					async: !!env.watch,
 					typescript: {
 						memoryLimit: 4096,
 					},