diff --git a/packages/@ngtools/webpack/src/plugin.ts b/packages/@ngtools/webpack/src/plugin.ts
index bff8a01e15ef..0ef52434a4b8 100644
--- a/packages/@ngtools/webpack/src/plugin.ts
+++ b/packages/@ngtools/webpack/src/plugin.ts
@@ -388,6 +388,11 @@ export class AotPlugin implements Tapable {
           return;
         }
 
+        // Create a new Program before compiling to get the latest source file contents,
+        // otherwise when using webpack-dev-server the files will be outdated at this point
+        this._program = ts.createProgram(
+          this._rootFilePath, this._compilerOptions, this._compilerHost, this._program);
+
         // Create the Code Generator.
         return __NGTOOLS_PRIVATE_API_2.codeGen({
           basePath: this._basePath,