diff --git a/packages/nextjs/src/config/webpack.ts b/packages/nextjs/src/config/webpack.ts
index 4484b1194bd2..df32c31f392e 100644
--- a/packages/nextjs/src/config/webpack.ts
+++ b/packages/nextjs/src/config/webpack.ts
@@ -276,7 +276,8 @@ export function constructWebpackConfigFunction({
       });
 
       // Wrap middleware
-      if (userSentryOptions.autoInstrumentMiddleware ?? true) {
+      const canWrapStandaloneMiddleware = userNextConfig.output !== 'standalone' || !major || major < 16;
+      if ((userSentryOptions.autoInstrumentMiddleware ?? true) && canWrapStandaloneMiddleware) {
         newConfig.module.rules.unshift({
           test: isMiddlewareResource,
           use: [