diff --git a/app/Console/Commands/EmailDoToVTCommand.php b/app/Console/Commands/EmailDoToVTCommand.php
index cf5100a6..aa5c7cf0 100644
--- a/app/Console/Commands/EmailDoToVTCommand.php
+++ b/app/Console/Commands/EmailDoToVTCommand.php
@@ -72,7 +72,9 @@ class EmailDoToVTCommand extends Command
 
             foreach ($bookings as $booking) {
                 $file = $booking->documents()->where('document_type', DocumentType::SUPPLIER_DELIVER_ORDER)->first()->files()->first();
-                $zip->addFile(Storage::disk('documents')->path($file->file->file_info->original->file), $booking->created_at->format('d_m_Y').'_'.$booking->marking.'.pdf');
+                if(!$zip->addFile(Storage::disk('documents')->path($file->file->file_info->original->file), $booking->created_at->format('d_m_Y').'_'.$booking->marking.'.pdf')){
+                    echo 'Could not add file to ZIP: ' . $file;
+                }
             }
 dd($zip);
             $zip->close();