diff --git a/src/App.php b/src/App.php
index f882b74..5224c55 100644
--- a/src/App.php
+++ b/src/App.php
@@ -2014,7 +2014,7 @@ final class App
         $fileName = $date . '-' . substr($hash, 0, 16) . '.' . $targetExtension;
         $target = $directory . '/' . $fileName;
 
-        if (is_file($target)) {
+        if (is_file($target) && $targetExtension !== 'webp') {
             return $fileName;
         }
 
@@ -2052,6 +2052,8 @@ final class App
             return false;
         }
 
+        $source = $this->applyImageOrientation($source, $sourcePath, $mime);
+
         $width = imagesx($source);
         $height = imagesy($source);
         if ($width <= 0 || $height <= 0) {
@@ -2080,6 +2082,30 @@ final class App
         return $written && is_file($target);
     }
 
+    private function applyImageOrientation(GdImage $source, string $sourcePath, string $mime): GdImage
+    {
+        if ($mime !== 'image/jpeg' || !function_exists('exif_read_data')) {
+            return $source;
+        }
+
+        $exif = @exif_read_data($sourcePath);
+        $orientation = is_array($exif) ? (int) ($exif['Orientation'] ?? 1) : 1;
+        $oriented = match ($orientation) {
+            3 => imagerotate($source, 180, 0),
+            6 => imagerotate($source, -90, 0),
+            8 => imagerotate($source, 90, 0),
+            default => $source,
+        };
+
+        if ($oriented instanceof GdImage && $oriented !== $source) {
+            imagedestroy($source);
+
+            return $oriented;
+        }
+
+        return $source;
+    }
+
     private function deleteDashboardImage(string $username, string $fileName): void
     {
         $fileName = basename(trim($fileName));