diff --git a/resources/server/router.php b/resources/server/router.php
index a4c043218..9660daec0 100644
--- a/resources/server/router.php
+++ b/resources/server/router.php
@@ -144,26 +144,19 @@
 $headersFile = $_SERVER['DOCUMENT_ROOT'] . '/../' . SERVER_TMP_DIR . '/headers.ini';
 if (file_exists($headersFile)) {
     $headersArray = parse_ini_file($headersFile, true);
-    // joker path tree
-    $pathParts = explode('/', pathinfo($path, PATHINFO_DIRNAME));
-    $previous = '';
-    for ($i = 0; $i < \count($pathParts); $i++) {
-        $headersSectionKey = $previous . \sprintf('/%s/*', trim($pathParts[$i], '\\'));
-        $previous .= '/' . $pathParts[$i];
-        $headersSectionKey = '/' . trim($headersSectionKey, '/');
-        if (\array_key_exists($headersSectionKey, $headersArray)) {
-            foreach ($headersArray[$headersSectionKey] as $key => $value) {
-                header("$key: " . $value);
+    // path with wildcard
+    foreach ($headersArray as $source => $headers) {
+        list($match) = sscanf($path, str_replace('*', '%s', $source));
+        if ($match !== null) {
+            foreach ($headers as $key => $value) {
+                header("$key: $value");
             }
         }
-        if (empty($pathParts[1])) {
-            break;
-        }
     }
     // exact file path
     if (\array_key_exists($path, $headersArray)) {
         foreach ($headersArray[$path] as $key => $value) {
-            header("$key: " . $value);
+            header("$key: $value");
         }
     }
 }
diff --git a/src/Command/Serve.php b/src/Command/Serve.php
index e25564572..55fa3892b 100644
--- a/src/Command/Serve.php
+++ b/src/Command/Serve.php
@@ -248,6 +248,7 @@ private function buildSuccess(OutputInterface $output): void
         // writes `headers.ini` file
         if (null !== $headers = $this->getBuilder()->getConfig()->get('headers')) {
             $output->writeln('Writing headers file...');
+            Util\File::getFS()->remove(Util::joinFile($this->getPath(), self::TMP_DIR, 'headers.ini'));
             foreach ($headers as $header) {
                 Util\File::getFS()->appendToFile(Util::joinFile($this->getPath(), self::TMP_DIR, 'headers.ini'), "[{$header['source']}]\n");
                 foreach ($header['headers'] as $h) {