diff --git a/app/Events/Document/DocumentSending.php b/app/Events/Document/DocumentSending.php
new file mode 100644
index 000000000..97db6503e
--- /dev/null
+++ b/app/Events/Document/DocumentSending.php
@@ -0,0 +1,20 @@
+<?php
+
+namespace App\Events\Document;
+
+use App\Abstracts\Event;
+
+class DocumentSending extends Event
+{
+    public $document;
+
+    /**
+     * Create a new event instance.
+     *
+     * @param $document
+     */
+    public function __construct($document)
+    {
+        $this->document = $document;
+    }
+}
diff --git a/app/Http/Controllers/Sales/Invoices.php b/app/Http/Controllers/Sales/Invoices.php
index be3f68250..04502c8ea 100644
--- a/app/Http/Controllers/Sales/Invoices.php
+++ b/app/Http/Controllers/Sales/Invoices.php
@@ -10,6 +10,7 @@ use App\Imports\Sales\Invoices as Import;
 use App\Jobs\Document\CreateDocument;
 use App\Jobs\Document\DeleteDocument;
 use App\Jobs\Document\DuplicateDocument;
+use App\Jobs\Document\SendDocument;
 use App\Jobs\Document\UpdateDocument;
 use App\Models\Document\Document;
 use App\Notifications\Sale\Invoice as Notification;
@@ -260,12 +261,17 @@ class Invoices extends Controller
             return redirect()->back();
         }
 
-        // Notify the customer
-        $invoice->contact->notify(new Notification($invoice, 'invoice_new_customer', true));
+        $response = $this->ajaxDispatch(new SendDocument($invoice));
 
-        event(new \App\Events\Document\DocumentSent($invoice));
+        if ($response['success']) {
+            $message = trans('documents.messages.email_sent', ['type' => trans_choice('general.invoices', 1)]);
 
-        flash(trans('documents.messages.email_sent', ['type' => trans_choice('general.invoices', 1)]))->success();
+            flash($message)->success();
+        } else {
+            $message = $response['message'];
+
+            flash($message)->error()->important();
+        }
 
         return redirect()->back();
     }
diff --git a/app/Jobs/Document/SendDocument.php b/app/Jobs/Document/SendDocument.php
new file mode 100644
index 000000000..62e271a68
--- /dev/null
+++ b/app/Jobs/Document/SendDocument.php
@@ -0,0 +1,26 @@
+<?php
+
+namespace App\Jobs\Document;
+
+use App\Abstracts\Job;
+use App\Events\Document\DocumentSending;
+use App\Events\Document\DocumentSent;
+use App\Models\Document\Document;
+
+class SendDocument extends Job
+{
+    public function __construct(Document $document)
+    {
+        $this->document = $document;
+    }
+
+    public function handle(): void
+    {
+        event(new DocumentSending($document));
+
+        // Notify the customer
+        $invoice->contact->notify(new Notification($invoice, 'invoice_new_customer', true));
+
+        event(new DocumentSent($document));
+    }
+}
diff --git a/app/Jobs/Document/SendDocumentAsCustomMail.php b/app/Jobs/Document/SendDocumentAsCustomMail.php
index cbc44d313..db8540437 100644
--- a/app/Jobs/Document/SendDocumentAsCustomMail.php
+++ b/app/Jobs/Document/SendDocumentAsCustomMail.php
@@ -3,6 +3,7 @@
 namespace App\Jobs\Document;
 
 use App\Abstracts\Job;
+use App\Events\Document\DocumentSending;
 use App\Events\Document\DocumentSent;
 use App\Models\Document\Document;
 
@@ -18,6 +19,8 @@ class SendDocumentAsCustomMail extends Job
     {
         $document = Document::find($this->request->get('document_id'));
 
+        event(new DocumentSending($document));
+
         $custom_mail = $this->request->only(['to', 'subject', 'body']);
 
         if ($this->request->get('user_email', false)) {