diff --git a/app/Http/Controllers/CreditController.php b/app/Http/Controllers/CreditController.php
index 41a035074f7c..7a7dcc6cb104 100644
--- a/app/Http/Controllers/CreditController.php
+++ b/app/Http/Controllers/CreditController.php
@@ -376,6 +376,8 @@ class CreditController extends BaseController
 
         $credit = $this->credit_repository->save($request->all(), $credit);
 
+        $credit->service()->deletePdf();
+        
         event(new CreditWasUpdated($credit, $credit->company, Ninja::eventVars()));
 
         return $this->itemResponse($credit);
diff --git a/app/Http/Controllers/QuoteController.php b/app/Http/Controllers/QuoteController.php
index ae2c8a750dde..e4cb852c767b 100644
--- a/app/Http/Controllers/QuoteController.php
+++ b/app/Http/Controllers/QuoteController.php
@@ -387,6 +387,8 @@ class QuoteController extends BaseController
 
         $quote = $this->quote_repo->save($request->all(), $quote);
 
+        $quote->service()->deletePdf();
+        
         event(new QuoteWasUpdated($quote, $quote->company, Ninja::eventVars()));
 
         return $this->itemResponse($quote);
diff --git a/app/Http/Controllers/RecurringInvoiceController.php b/app/Http/Controllers/RecurringInvoiceController.php
index e36a8f624924..5acf54ac66f6 100644
--- a/app/Http/Controllers/RecurringInvoiceController.php
+++ b/app/Http/Controllers/RecurringInvoiceController.php
@@ -374,6 +374,8 @@ class RecurringInvoiceController extends BaseController
 
         $recurring_invoice = $this->recurring_invoice_repo->save($request->all(), $recurring_invoice);
 
+        $recurring_invoice->service()->deletePdf()->save();
+
         return $this->itemResponse($recurring_invoice);
     }
 
diff --git a/app/Services/Credit/CreditService.php b/app/Services/Credit/CreditService.php
index 8912c41e3561..4af43a348363 100644
--- a/app/Services/Credit/CreditService.php
+++ b/app/Services/Credit/CreditService.php
@@ -88,6 +88,8 @@ class CreditService
     {
         $this->credit = (new ApplyPayment($this->credit, $invoice, $amount, $payment))->run();
 
+        $this->deletePdf();
+        
         return $this;
     }
 
diff --git a/app/Services/Credit/MarkSent.php b/app/Services/Credit/MarkSent.php
index 8b0ffbf223a1..5b9418e02416 100644
--- a/app/Services/Credit/MarkSent.php
+++ b/app/Services/Credit/MarkSent.php
@@ -44,6 +44,7 @@ class MarkSent
              ->setStatus(Credit::STATUS_SENT)
              ->applyNumber()
              ->adjustBalance($this->credit->amount)
+             ->deletePdf()
              ->save();
 
 
diff --git a/app/Services/Quote/MarkSent.php b/app/Services/Quote/MarkSent.php
index a80747b34c93..aebe2d4b35a2 100644
--- a/app/Services/Quote/MarkSent.php
+++ b/app/Services/Quote/MarkSent.php
@@ -43,6 +43,7 @@ class MarkSent
              ->service()
              ->setStatus(Quote::STATUS_SENT)
              ->applyNumber()
+             ->deletePdf()
              ->save();
 
         return $this->quote;
diff --git a/app/Services/Quote/QuoteService.php b/app/Services/Quote/QuoteService.php
index 01488348d12c..642b9c594992 100644
--- a/app/Services/Quote/QuoteService.php
+++ b/app/Services/Quote/QuoteService.php
@@ -39,21 +39,6 @@ class QuoteService
         return $this;
     }
 
-    // public function markApproved()
-    // {
-    //     $mark_approved = new MarkApproved($this->quote->client);
-    //     $this->quote = $mark_approved->run($this->quote);
-
-    //     if ($this->quote->client->getSetting('auto_convert_quote') == true) {
-    //         $this->convert();
-    //     }
-
-    //     $this->markSent()
-    //          ->createInvitations();
-
-    //     return $this;
-    // }
-
     public function convert() :self
     {
         if ($this->quote->invoice_id) {
@@ -127,6 +112,7 @@ class QuoteService
                  ->service()
                  ->markSent()
                  ->createInvitations()
+                 ->deletePdf()
                  ->save();
 
         }