diff --git a/app/Http/Controllers/SmtpController.php b/app/Http/Controllers/SmtpController.php
index edfc24c38689..629a92bc1b48 100644
--- a/app/Http/Controllers/SmtpController.php
+++ b/app/Http/Controllers/SmtpController.php
@@ -55,7 +55,17 @@ class SmtpController extends BaseController
         (new \Illuminate\Mail\MailServiceProvider(app()))->register();
 
         try {
-            Mail::mailer('smtp')->to($user->email, $user->present()->name())->send(new TestMailServer('Email Server Works!', strlen($company->settings->custom_sending_email) > 1 ? $company->settings->custom_sending_email : $user->email));
+
+            $sending_email = (isset($company->settings->custom_sending_email) && stripos($company->settings->custom_sending_email, "@")) ? $company->settings->custom_sending_email : $user->email;
+            $sending_user = (isset($company->settings->email_from_name) && strlen($company->settings->email_from_name) > 2) ? $company->settings->email_from_name : $user->name();
+
+            $mailable = new TestMailServer('Email Server Works!', $sending_email);
+            $mailable->from($sending_email,$sending_user);
+
+            Mail::mailer('smtp')
+                ->to($user->email, $user->present()->name())
+                ->send($mailable);
+
         } catch (\Exception $e) {
             app('mail.manager')->forgetMailers();
             return response()->json(['message' => $e->getMessage()], 400);        
diff --git a/app/Jobs/RecurringInvoice/SendRecurring.php b/app/Jobs/RecurringInvoice/SendRecurring.php
index def24172b528..5bed2111b564 100644
--- a/app/Jobs/RecurringInvoice/SendRecurring.php
+++ b/app/Jobs/RecurringInvoice/SendRecurring.php
@@ -76,12 +76,12 @@ class SendRecurring implements ShouldQueue
             $invoice = $invoice->service()
                                ->markSent()
                                ->applyNumber()
-                               ->fillDefaults()
+                               ->fillDefaults(true)
                                ->adjustInventory()
                                ->save();
         } else {
             $invoice = $invoice->service()
-                               ->fillDefaults()
+                               ->fillDefaults(true)
                                ->save();
         }
 
diff --git a/app/Services/Invoice/InvoiceService.php b/app/Services/Invoice/InvoiceService.php
index effe34daceba..dbe57e361b3c 100644
--- a/app/Services/Invoice/InvoiceService.php
+++ b/app/Services/Invoice/InvoiceService.php
@@ -544,7 +544,7 @@ class InvoiceService
         return $this;
     }
 
-    public function fillDefaults()
+    public function fillDefaults(bool $is_recurring = false)
     {
         $this->invoice->load('client.company');
 
@@ -571,7 +571,7 @@ class InvoiceService
             $this->invoice->exchange_rate = $this->invoice->client->setExchangeRate();
         }
 
-        if ($this->invoice->client->getSetting('auto_bill_standard_invoices')) {
+        if ($is_recurring && $this->invoice->client->getSetting('auto_bill_standard_invoices')) {
             $this->invoice->auto_bill_enabled = true;
         }