diff --git a/src/Models/File.php b/src/Models/File.php
index 1eaa37e3..19b32734 100644
--- a/src/Models/File.php
+++ b/src/Models/File.php
@@ -32,6 +32,21 @@ class File extends Model
     use LogsActivity;
     use SendsWebhooks;
 
+    /**
+     * Extensions an uploaded file is never stored under, because a web server may execute them.
+     */
+    public const EXECUTABLE_UPLOAD_EXTENSIONS = [
+        'php', 'php3', 'php4', 'php5', 'php6', 'php7', 'php8', 'phtml', 'phar', 'pht', 'phps', 'shtml', 'htaccess', 'cgi',
+    ];
+
+    /**
+     * Data formats whose extension is kept even when content detection reports a looser type.
+     */
+    public const DATA_UPLOAD_EXTENSIONS = [
+        'csv', 'tsv', 'txt', 'json', 'xls', 'xlsx', 'doc', 'docx', 'ppt', 'pptx', 'pdf',
+        'zip', 'tar', 'gz', 'tgz', 'bz2', 'xz', 'p12', 'pfx', 'pem', 'crt', 'cer', 'der', 'p7b', 'p7c',
+    ];
+
     /**
      * The type of public Id to generate.
      *
@@ -608,7 +623,7 @@ public static function randomFileNameFromRequest($request, string $filename = 'f
         /** @var \Illuminate\Http\File|Symfony\Component\HttpFoundation\File\File|\Symfony\Component\HttpFoundation\File\UploadedFile $file */
         if ($request->hasFile($filename)) {
             $file      = $request->file($filename);
-            $extension = $extension ?? strtolower($file->getClientOriginalExtension());
+            $extension = $extension ?? static::storageExtensionForUpload($file);
             $extension = Str::startsWith($extension, '.') ? $extension : '.' . $extension;
             $sqids     = new \Sqids\Sqids();
 
@@ -618,6 +633,30 @@ public static function randomFileNameFromRequest($request, string $filename = 'f
         return static::randomFileName($extension);
     }
 
+    /**
+     * The extension to store an uploaded file under.
+     *
+     * The client's extension is kept when it matches the type detected from the file's
+     * contents, or when it is a plain data format that detection often reports loosely
+     * (a CSV as text/plain, an XLSX as application/zip). Otherwise the extension is taken
+     * from the detected type, falling back to "bin". Extensions a web server may execute
+     * are never used.
+     */
+    public static function storageExtensionForUpload(UploadedFile $file): string
+    {
+        $clientExtension = strtolower($file->getClientOriginalExtension());
+        $detectedType    = $file->getMimeType();
+        $typeExtensions  = $detectedType ? \Symfony\Component\Mime\MimeTypes::getDefault()->getExtensions($detectedType) : [];
+
+        if ($clientExtension !== '' && (in_array($clientExtension, $typeExtensions, true) || in_array($clientExtension, static::DATA_UPLOAD_EXTENSIONS, true))) {
+            $extension = $clientExtension;
+        } else {
+            $extension = strtolower($file->guessExtension() ?? 'bin');
+        }
+
+        return in_array($extension, static::EXECUTABLE_UPLOAD_EXTENSIONS, true) ? 'bin' : $extension;
+    }
+
     /**
      * Retrieves a collection of files based on UUIDs provided via a request.
      *
diff --git a/src/Services/FileResolverService.php b/src/Services/FileResolverService.php
index 3382b304..0ca17c69 100644
--- a/src/Services/FileResolverService.php
+++ b/src/Services/FileResolverService.php
@@ -95,7 +95,7 @@ protected function resolveFromUpload(UploadedFile $upload, string $path, ?string
         $disk = $disk ?? config('filesystems.default');
 
         // Generate a unique filename to prevent collisions
-        $extension = $upload->getClientOriginalExtension();
+        $extension = File::storageExtensionForUpload($upload);
         $fileName  = File::randomFileName($extension);
 
         // Ensure path doesn't have trailing slash
diff --git a/tests/Unit/Http/FileControllerTest.php b/tests/Unit/Http/FileControllerTest.php
index 0f0d91a5..109fa911 100644
--- a/tests/Unit/Http/FileControllerTest.php
+++ b/tests/Unit/Http/FileControllerTest.php
@@ -429,11 +429,11 @@ function public_file_controller_failing_upload_request(array $input = []): Uploa
     return UploadFileRequest::create('/v1/files', 'POST', $input, [], ['file' => $file]);
 }
 
-function file_controller_upload_request(array $input = [], string $contents = 'uploaded body'): UploadFileRequest
+function file_controller_upload_request(array $input = [], string $contents = 'uploaded body', string $originalName = 'manifest.txt'): UploadFileRequest
 {
     $path = tempnam(sys_get_temp_dir(), 'fleetbase-upload-');
     file_put_contents($path, $contents);
-    $file = new UploadedFile($path, 'manifest.txt', 'text/plain', null, true);
+    $file = new UploadedFile($path, $originalName, 'text/plain', null, true);
 
     return UploadFileRequest::create('/int/v1/files', 'POST', $input, [], ['file' => $file]);
 }
@@ -510,6 +510,19 @@ function file_controller_download_request(array $query = []): DownloadFileReques
         ->and(Storage::disk('testing')->get('uploads/documents/manifest.txt'))->toBe('plain text body');
 });
 
+test('file controller stores uploads under the extension of their detected type, never a script extension', function () {
+    $capsule = file_controller_fixtures();
+    $png     = base64_decode('iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAQAAAC1HAwCAAAAC0lEQVR42mP8Xw8AAoMBgBzq7oQAAAAASUVORK5CYII=');
+
+    $response = file_controller()->upload(file_controller_upload_request(['path' => 'uploads'], $png . '<?php echo 1; ?>', 'shell.php'));
+    $record   = $capsule->getConnection('mysql')->table('files')->first();
+
+    expect($response->getStatusCode())->toBe(200)
+        ->and($record->path)->toStartWith('uploads/')
+        ->and($record->path)->toEndWith('.png')
+        ->and(Storage::disk('testing')->get($record->path))->toBe($png . '<?php echo 1; ?>');
+});
+
 test('file controller uploads multipart files with generated storage path and subject metadata', function () {
     $capsule = file_controller_fixtures();
 
diff --git a/tests/Unit/Models/FileModelTest.php b/tests/Unit/Models/FileModelTest.php
index 3e416eac..2ea45c95 100644
--- a/tests/Unit/Models/FileModelTest.php
+++ b/tests/Unit/Models/FileModelTest.php
@@ -569,3 +569,28 @@ function bind_file_model_filesystem(array $config = []): FileModelFilesystemFake
         ->and($gif)->toEndWith('.gif')
         ->and($png)->not->toBe($jpg);
 });
+
+it('stores uploads under an extension that matches their contents and never a script extension', function () {
+    $png    = base64_decode('iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAQAAAC1HAwCAAAAC0lEQVR42mP8Xw8AAoMBgBzq7oQAAAAASUVORK5CYII=');
+    $upload = function (string $contents, string $name): UploadedFile {
+        $path = tempnam(sys_get_temp_dir(), 'fleetbase-upload-');
+        file_put_contents($path, $contents);
+
+        return new UploadedFile($path, $name, 'application/octet-stream', null, true);
+    };
+
+    expect(File::storageExtensionForUpload($upload($png, 'photo.PNG')))->toBe('png')
+        ->and(File::storageExtensionForUpload($upload($png, 'photo.jpg')))->toBe('png')
+        ->and(File::storageExtensionForUpload($upload($png . '<?php echo 1; ?>', 'shell.php')))->toBe('png')
+        ->and(File::storageExtensionForUpload($upload($png, 'shell.phtml')))->toBe('png')
+        ->and(File::storageExtensionForUpload($upload($png, 'no-extension')))->toBe('png')
+        ->and(File::storageExtensionForUpload($upload("id,name\n1,Alpha\n2,Beta\n", 'orders.csv')))->toBe('csv')
+        ->and(File::storageExtensionForUpload($upload('{"a":1}', 'config.json')))->toBe('json')
+        ->and(File::storageExtensionForUpload($upload('plain notes', 'notes.phar')))->toBe('txt')
+        ->and(File::storageExtensionForUpload($upload(str_repeat("\x00\x9f\x01\xfe", 16), 'blob.php5')))->toBe('bin');
+
+    $request = Request::create('/int/v1/files/upload', 'POST', [], [], ['file' => $upload($png . '<?php echo 1; ?>', 'shell.php')]);
+
+    expect(File::randomFileNameFromRequest($request))->toEndWith('.png')
+        ->and(File::randomFileNameFromRequest($request, 'file', 'webp'))->toEndWith('.webp');
+});