diff --git a/bundle/Controller/Resource/Upload.php b/bundle/Controller/Resource/Upload.php
index 38efe578..052dbb51 100644
--- a/bundle/Controller/Resource/Upload.php
+++ b/bundle/Controller/Resource/Upload.php
@@ -18,9 +18,23 @@
 use Symfony\Component\HttpFoundation\Response;
 use Symfony\Contracts\Translation\TranslatorInterface;
 
+use function fclose;
+use function filesize;
+use function fopen;
+use function fread;
+use function fseek;
 use function implode;
 use function in_array;
 use function is_array;
+use function is_file;
+use function is_readable;
+use function preg_match;
+use function strpos;
+use function strrpos;
+use function strtolower;
+use function substr;
+
+use const SEEK_END;
 
 final class Upload extends AbstractController
 {
@@ -88,9 +102,11 @@ public function __invoke(Request $request): Response
 
         $md5 = $this->fileHashFactory->createHash($file->getRealPath());
         $fileStruct = FileStruct::fromUploadedFile($file);
+
+        $resourceType = $this->isEncryptedPdf($file) ? 'raw' : 'auto';
         $resourceStruct = new ResourceStruct(
             $fileStruct,
-            'auto',
+            $resourceType,
             $folder,
             $visibility,
             $request->request->get('filename'),
@@ -113,4 +129,47 @@ public function __invoke(Request $request): Response
 
         return new JsonResponse($this->formatResource($resource), $httpCode);
     }
+
+    private function isEncryptedPdf(UploadedFile $file): bool
+    {
+        if (strtolower($file->getClientOriginalExtension()) !== 'pdf') {
+            return false;
+        }
+
+        $path = (string) $file->getRealPath();
+        if ($path === '' || !is_file($path) || !is_readable($path)) {
+            return false;
+        }
+
+        $fp = @fopen($path, 'r');
+        if ($fp === false) {
+            return false;
+        }
+
+        $fileSize = filesize($path);
+
+        if ($fileSize !== false && $fileSize <= 20480) {
+            $content = (string) fread($fp, $fileSize);
+        } else {
+            $head = (string) fread($fp, 4096);
+
+            @fseek($fp, -16384, SEEK_END);
+            $tail = (string) fread($fp, 16384);
+
+            $content = $head . $tail;
+        }
+
+        fclose($fp);
+
+        if (strpos($content, '%PDF-') !== 0) {
+            return false;
+        }
+
+        $eofPos = strrpos($content, '%%EOF');
+        if ($eofPos !== false) {
+            $content = substr($content, 0, $eofPos + 5);
+        }
+
+        return (bool) preg_match('/\/(?:Encrypt)\s+(\d+|<<)/m', $content);
+    }
 }
diff --git a/tests/bundle/Controller/Resource/UploadTest.php b/tests/bundle/Controller/Resource/UploadTest.php
index 50a2ed59..1d406cb5 100644
--- a/tests/bundle/Controller/Resource/UploadTest.php
+++ b/tests/bundle/Controller/Resource/UploadTest.php
@@ -27,7 +27,11 @@
 use Symfony\Component\HttpFoundation\Response;
 use Symfony\Contracts\Translation\TranslatorInterface;
 
+use function file_put_contents;
 use function json_encode;
+use function sys_get_temp_dir;
+use function tempnam;
+use function unlink;
 
 #[CoversClass(UploadController::class)]
 #[CoversClass(AbstractController::class)]
@@ -78,7 +82,7 @@ public function testUpload(): void
             ->willReturn('sample_image');
 
         $uploadedFileMock
-            ->expects(self::exactly(2))
+            ->expects(self::exactly(3))
             ->method('getClientOriginalExtension')
             ->willReturn('jpg');
 
@@ -179,6 +183,265 @@ public function testUpload(): void
         );
     }
 
+    public function testUploadEncryptedPdfIsRaw(): void
+    {
+        $tmpPdfPath = (string) tempnam(sys_get_temp_dir(), 'ngrm_encrypted_pdf_');
+        file_put_contents($tmpPdfPath, "%PDF-1.7\n1 0 obj\n<< /Encrypt 2 0 R >>\nendobj\n");
+
+        $request = new Request();
+        $request->request->add([
+            'folder' => 'media/document',
+        ]);
+
+        $uploadedFileMock = $this->createMock(UploadedFile::class);
+
+        $uploadedFileMock
+            ->expects(self::once())
+            ->method('isFile')
+            ->willReturn(true);
+
+        // getRealPath is used for md5 hash + FileStruct + encryption detector
+        $uploadedFileMock
+            ->expects(self::exactly(4))
+            ->method('getRealPath')
+            ->willReturn($tmpPdfPath);
+
+        $uploadedFileMock
+            ->expects(self::exactly(2))
+            ->method('getClientOriginalName')
+            ->willReturn('protected.pdf');
+
+        // getClientOriginalExtension is used for FileStruct + encryption detector
+        $uploadedFileMock
+            ->expects(self::exactly(3))
+            ->method('getClientOriginalExtension')
+            ->willReturn('pdf');
+
+        $request->files->add([
+            'file' => $uploadedFileMock,
+        ]);
+
+        $this->fileHashFactoryMock
+            ->expects(self::once())
+            ->method('createHash')
+            ->with($tmpPdfPath)
+            ->willReturn('md5hash');
+
+        $fileStruct = FileStruct::fromUploadedFile($uploadedFileMock);
+
+        $resourceStruct = new ResourceStruct(
+            $fileStruct,
+            'raw',
+            Folder::fromPath('media/document'),
+            'public',
+            $request->request->get('filename'),
+        );
+
+        $resource = new RemoteResource(
+            remoteId: 'upload|raw|media/document/protected.pdf',
+            type: 'raw',
+            url: 'https://cloudinary.com/test/upload/raw/media/document/protected.pdf',
+            md5: 'md5hash',
+            name: 'protected.pdf',
+            folder: Folder::fromPath('media/document'),
+            size: 123,
+        );
+
+        $this->providerMock
+            ->expects(self::once())
+            ->method('upload')
+            ->with($resourceStruct)
+            ->willReturn($resource);
+
+        $this->providerMock
+            ->expects(self::exactly(0))
+            ->method('buildVariation')
+            ->willReturnCallback(
+                static fn () => new RemoteResourceVariation(
+                    $resource,
+                    'https://cloudinary.com/test/variation/url',
+                ),
+            );
+
+        $response = $this->controller->__invoke($request);
+
+        self::assertInstanceOf(JsonResponse::class, $response);
+
+        unlink($tmpPdfPath);
+    }
+
+    public function testUploadPdfWithEncryptInMetadataIsAuto(): void
+    {
+        $tmpPdfPath = (string) tempnam(sys_get_temp_dir(), 'ngrm_unencrypted_pdf_metadata_');
+        file_put_contents(
+            $tmpPdfPath,
+            "%PDF-1.7\n1 0 obj\n<< /Type /Catalog >>\nendobj\n"
+            . "/Title (/Encrypt)\n"
+            . "%%EOF\n",
+        );
+
+        $request = new Request();
+        $request->request->add([
+            'folder' => 'media/document',
+        ]);
+
+        $uploadedFileMock = $this->createMock(UploadedFile::class);
+
+        $uploadedFileMock
+            ->expects(self::once())
+            ->method('isFile')
+            ->willReturn(true);
+
+        // getRealPath is used for md5 hash + FileStruct + encryption detector
+        $uploadedFileMock
+            ->expects(self::exactly(4))
+            ->method('getRealPath')
+            ->willReturn($tmpPdfPath);
+
+        $uploadedFileMock
+            ->expects(self::exactly(2))
+            ->method('getClientOriginalName')
+            ->willReturn('unencrypted.pdf');
+
+        // getClientOriginalExtension is used for FileStruct + encryption detector
+        $uploadedFileMock
+            ->expects(self::exactly(3))
+            ->method('getClientOriginalExtension')
+            ->willReturn('pdf');
+
+        $request->files->add([
+            'file' => $uploadedFileMock,
+        ]);
+
+        $this->fileHashFactoryMock
+            ->expects(self::once())
+            ->method('createHash')
+            ->with($tmpPdfPath)
+            ->willReturn('md5hash');
+
+        $fileStruct = FileStruct::fromUploadedFile($uploadedFileMock);
+
+        $resourceStruct = new ResourceStruct(
+            $fileStruct,
+            'auto',
+            Folder::fromPath('media/document'),
+            'public',
+            $request->request->get('filename'),
+        );
+
+        $resource = new RemoteResource(
+            remoteId: 'upload|auto|media/document/unencrypted.pdf',
+            type: 'auto',
+            url: 'https://cloudinary.com/test/upload/auto/media/document/unencrypted.pdf',
+            md5: 'md5hash',
+            name: 'unencrypted.pdf',
+            folder: Folder::fromPath('media/document'),
+            size: 123,
+        );
+
+        $this->providerMock
+            ->expects(self::once())
+            ->method('upload')
+            ->with($resourceStruct)
+            ->willReturn($resource);
+
+        $this->providerMock
+            ->expects(self::exactly(0))
+            ->method('buildVariation');
+
+        $response = $this->controller->__invoke($request);
+
+        self::assertInstanceOf(JsonResponse::class, $response);
+
+        unlink($tmpPdfPath);
+    }
+
+    public function testUploadPdfWithEncryptInTrailingCommentAfterEofIsAuto(): void
+    {
+        $tmpPdfPath = (string) tempnam(sys_get_temp_dir(), 'ngrm_unencrypted_pdf_comment_');
+        file_put_contents(
+            $tmpPdfPath,
+            "%PDF-1.7\n1 0 obj\n<< /Type /Catalog >>\nendobj\n"
+            . "%%EOF\n"
+            . "% /Encrypt 2 0 R\n",
+        );
+
+        $request = new Request();
+        $request->request->add([
+            'folder' => 'media/document',
+        ]);
+
+        $uploadedFileMock = $this->createMock(UploadedFile::class);
+
+        $uploadedFileMock
+            ->expects(self::once())
+            ->method('isFile')
+            ->willReturn(true);
+
+        // getRealPath is used for md5 hash + FileStruct + encryption detector
+        $uploadedFileMock
+            ->expects(self::exactly(4))
+            ->method('getRealPath')
+            ->willReturn($tmpPdfPath);
+
+        $uploadedFileMock
+            ->expects(self::exactly(2))
+            ->method('getClientOriginalName')
+            ->willReturn('unencrypted.pdf');
+
+        // getClientOriginalExtension is used for FileStruct + encryption detector
+        $uploadedFileMock
+            ->expects(self::exactly(3))
+            ->method('getClientOriginalExtension')
+            ->willReturn('pdf');
+
+        $request->files->add([
+            'file' => $uploadedFileMock,
+        ]);
+
+        $this->fileHashFactoryMock
+            ->expects(self::once())
+            ->method('createHash')
+            ->with($tmpPdfPath)
+            ->willReturn('md5hash');
+
+        $fileStruct = FileStruct::fromUploadedFile($uploadedFileMock);
+
+        $resourceStruct = new ResourceStruct(
+            $fileStruct,
+            'auto',
+            Folder::fromPath('media/document'),
+            'public',
+            $request->request->get('filename'),
+        );
+
+        $resource = new RemoteResource(
+            remoteId: 'upload|auto|media/document/unencrypted.pdf',
+            type: 'auto',
+            url: 'https://cloudinary.com/test/upload/auto/media/document/unencrypted.pdf',
+            md5: 'md5hash',
+            name: 'unencrypted.pdf',
+            folder: Folder::fromPath('media/document'),
+            size: 123,
+        );
+
+        $this->providerMock
+            ->expects(self::once())
+            ->method('upload')
+            ->with($resourceStruct)
+            ->willReturn($resource);
+
+        $this->providerMock
+            ->expects(self::exactly(0))
+            ->method('buildVariation');
+
+        $response = $this->controller->__invoke($request);
+
+        self::assertInstanceOf(JsonResponse::class, $response);
+
+        unlink($tmpPdfPath);
+    }
+
     public function testUploadProtectedWithContext(): void
     {
         $uploadContext = [
@@ -211,7 +474,7 @@ public function testUploadProtectedWithContext(): void
             ->willReturn('sample_image');
 
         $uploadedFileMock
-            ->expects(self::exactly(2))
+            ->expects(self::exactly(3))
             ->method('getClientOriginalExtension')
             ->willReturn('jpg');
 
@@ -396,7 +659,7 @@ public function testUploadExistingFile(): void
             ->willReturn('sample_image');
 
         $uploadedFileMock
-            ->expects(self::exactly(2))
+            ->expects(self::exactly(3))
             ->method('getClientOriginalExtension')
             ->willReturn('jpg');
 
@@ -555,7 +818,7 @@ public function testUploadExistingFileName(): void
             ->willReturn('sample_image');
 
         $uploadedFileMock
-            ->expects(self::exactly(2))
+            ->expects(self::exactly(3))
             ->method('getClientOriginalExtension')
             ->willReturn('jpg');