diff --git a/src/dev/builder.ts b/src/dev/builder.ts
index 0934b1dfdcb..fbfd4b9b176 100644
--- a/src/dev/builder.ts
+++ b/src/dev/builder.ts
@@ -199,6 +199,7 @@ export class Builder implements FreshBuilder {
       buildCache.islands.set(island.name, `/${chunk}`);
     }
 
+    console.trace("FLUSH");
     await buildCache.flush();
 
     if (!dev) {
diff --git a/src/dev/builder_test.ts b/src/dev/builder_test.ts
index 8deb12ed302..0b10d4d9926 100644
--- a/src/dev/builder_test.ts
+++ b/src/dev/builder_test.ts
@@ -11,18 +11,21 @@ Deno.test({
     builder.onTransformStaticFile(
       { pluginName: "A", filter: /\.css$/ },
       () => {
+        console.trace();
         logs.push("A");
       },
     );
     builder.onTransformStaticFile(
       { pluginName: "B", filter: /\.css$/ },
       () => {
+        console.trace();
         logs.push("B");
       },
     );
     builder.onTransformStaticFile(
       { pluginName: "C", filter: /\.css$/ },
       () => {
+        console.trace();
         logs.push("C");
       },
     );
diff --git a/src/dev/dev_build_cache.ts b/src/dev/dev_build_cache.ts
index 5f200683848..5259475c3c3 100644
--- a/src/dev/dev_build_cache.ts
+++ b/src/dev/dev_build_cache.ts
@@ -143,6 +143,7 @@ export class MemoryBuildCache implements DevBuildCache {
 
   // deno-lint-ignore require-await
   async flush(): Promise<void> {
+    console.log("FLUSH MEMORY CACHE");
     this.#ready.resolve();
   }
 }
@@ -201,6 +202,7 @@ export class DiskBuildCache implements DevBuildCache {
 
   async flush(): Promise<void> {
     const staticDir = this.config.staticDir;
+    const outDir = this.config.build.outDir;
 
     if (await fsAdapter.isDirectory(staticDir)) {
       const entries = fsAdapter.walk(staticDir, {
@@ -212,6 +214,11 @@ export class DiskBuildCache implements DevBuildCache {
       });
 
       for await (const entry of entries) {
+        // OutDir might be inside static dir
+        if (!path.relative(outDir, entry.path).startsWith("..")) {
+          continue;
+        }
+
         const result = await this.#transformer.process(
           entry.path,
           "production",