diff --git a/app/Services/Credit/TriggeredActions.php b/app/Services/Credit/TriggeredActions.php
index 28134972a..cfc10e2d2 100644
--- a/app/Services/Credit/TriggeredActions.php
+++ b/app/Services/Credit/TriggeredActions.php
@@ -38,6 +38,7 @@ class TriggeredActions extends AbstractService
     {
 
         if ($this->request->has('send_email') && $this->request->input('send_email') == 'true') {
+            $this->credit = $this->credit->service()->markSent()->save();
             $this->sendEmail();
         }
 
diff --git a/app/Services/Invoice/TriggeredActions.php b/app/Services/Invoice/TriggeredActions.php
index f9b19f4b1..2636a5376 100644
--- a/app/Services/Invoice/TriggeredActions.php
+++ b/app/Services/Invoice/TriggeredActions.php
@@ -49,7 +49,7 @@ class TriggeredActions extends AbstractService
         }
 
         if ($this->request->has('send_email') && $this->request->input('send_email') == 'true') {
-            $this->invoice->service()->touchPdf()->save();
+            $this->invoice->service()->markSent()->touchPdf()->save();
             $this->sendEmail();
         }
 
diff --git a/app/Services/Quote/TriggeredActions.php b/app/Services/Quote/TriggeredActions.php
index fa630d753..ea38a696c 100644
--- a/app/Services/Quote/TriggeredActions.php
+++ b/app/Services/Quote/TriggeredActions.php
@@ -38,6 +38,7 @@ class TriggeredActions extends AbstractService
     {
 
         if ($this->request->has('send_email') && $this->request->input('send_email') == 'true') {
+            $this->quote = $this->quote->service()->markSent()->save();
             $this->sendEmail();
         }