diff --git a/app/Jobs/RecurringInvoice/SendRecurring.php b/app/Jobs/RecurringInvoice/SendRecurring.php
index 63ce5c2e030f..d19ebd3847f3 100644
--- a/app/Jobs/RecurringInvoice/SendRecurring.php
+++ b/app/Jobs/RecurringInvoice/SendRecurring.php
@@ -116,7 +116,7 @@ class SendRecurring implements ShouldQueue
         nlog("Invoice {$invoice->number} created");
 
         $invoice->invitations->each(function ($invitation) use ($invoice) {
-            if ($invitation->contact && strlen($invitation->contact->email) >=1 && $invoice->client->getSetting('auto_email_invoice')) {
+            if ($invitation->contact && !$invitation->contact->trashed() && strlen($invitation->contact->email) >=1 && $invoice->client->getSetting('auto_email_invoice')) {
 
                 try{
                     EmailEntity::dispatch($invitation, $invoice->company);
diff --git a/app/Jobs/Util/SendFailedEmails.php b/app/Jobs/Util/SendFailedEmails.php
index bffe66caa6eb..ae8f11be1d37 100644
--- a/app/Jobs/Util/SendFailedEmails.php
+++ b/app/Jobs/Util/SendFailedEmails.php
@@ -63,7 +63,7 @@ class SendFailedEmails implements ShouldQueue
             $invitation = $job_meta_array['entity_name']::where('key', $job_meta_array['invitation_key'])->with('contact')->first();
 
             if ($invitation->invoice) {
-                if ($invitation->contact->send_email && $invitation->contact->email) {
+                if (!$invitation->contact->trashed() && $invitation->contact->send_email && $invitation->contact->email) {
                     EmailEntity::dispatch($invitation, $invitation->company, $job_meta_array['reminder_template']);
                 }
             }
diff --git a/app/PaymentDrivers/BaseDriver.php b/app/PaymentDrivers/BaseDriver.php
index 65705fc19c9d..c715a9d46424 100644
--- a/app/PaymentDrivers/BaseDriver.php
+++ b/app/PaymentDrivers/BaseDriver.php
@@ -394,7 +394,7 @@ class BaseDriver extends AbstractPaymentDriver
 
         $invoices->first()->invitations->each(function ($invitation) use ($nmo){
 
-            if ($invitation->contact->send_email && $invitation->contact->email) {
+            if (!$invitation->contact->trashed() && $invitation->contact->send_email && $invitation->contact->email) {
 
                 $nmo->to_user = $invitation->contact;
                 NinjaMailerJob::dispatch($nmo);
@@ -456,7 +456,7 @@ class BaseDriver extends AbstractPaymentDriver
 
         $invoices->first()->invitations->each(function ($invitation) use ($nmo){
 
-            if ($invitation->contact->send_email && $invitation->contact->email) {
+            if (!$invitation->contact->trashed() && $invitation->contact->send_email && $invitation->contact->email) {
 
                 $nmo->to_user = $invitation->contact;
                 NinjaMailerJob::dispatch($nmo);
diff --git a/app/Services/Credit/SendEmail.php b/app/Services/Credit/SendEmail.php
index 3915b7503502..55599323f139 100644
--- a/app/Services/Credit/SendEmail.php
+++ b/app/Services/Credit/SendEmail.php
@@ -44,7 +44,7 @@ class SendEmail
         }
 
         $this->credit->invitations->each(function ($invitation) {
-            if ($invitation->contact->send_email && $invitation->contact->email) {
+            if (!$invitation->contact->trashed() && $invitation->contact->send_email && $invitation->contact->email) {
                 $email_builder = (new CreditEmail())->build($invitation, $this->reminder_template);
 
                 // EmailCredit::dispatchNow($email_builder, $invitation, $invitation->company);
diff --git a/app/Services/Invoice/SendEmail.php b/app/Services/Invoice/SendEmail.php
index 54cd0f326623..f96b95cbaabc 100644
--- a/app/Services/Invoice/SendEmail.php
+++ b/app/Services/Invoice/SendEmail.php
@@ -44,7 +44,7 @@ class SendEmail extends AbstractService
         }
 
         $this->invoice->invitations->each(function ($invitation) {
-            if ($invitation->contact->send_email && $invitation->contact->email) {
+            if (!$invitation->contact->trashed() && $invitation->contact->send_email && $invitation->contact->email) {
                 EmailEntity::dispatchNow($invitation, $invitation->company, $this->reminder_template);
             }
         });
diff --git a/app/Services/Quote/SendEmail.php b/app/Services/Quote/SendEmail.php
index 91ff69586505..8fb1c30024a0 100644
--- a/app/Services/Quote/SendEmail.php
+++ b/app/Services/Quote/SendEmail.php
@@ -42,7 +42,7 @@ class SendEmail
         }
 
         $this->quote->invitations->each(function ($invitation) {
-            if ($invitation->contact->send_email && $invitation->contact->email) {
+            if (!$invitation->contact->trashed() && $invitation->contact->send_email && $invitation->contact->email) {
                 EmailEntity::dispatchNow($invitation, $invitation->company, $this->reminder_template);
             }
         });
diff --git a/tests/Feature/CancelInvoiceTest.php b/tests/Feature/CancelInvoiceTest.php
index a4d5a8104cf7..5bdaf24e6b2b 100644
--- a/tests/Feature/CancelInvoiceTest.php
+++ b/tests/Feature/CancelInvoiceTest.php
@@ -54,11 +54,11 @@ class CancelInvoiceTest extends TestCase
 
         $this->assertEquals(Invoice::STATUS_SENT, $this->invoice->status_id);
 
-        $this->invoice->service()->handleCancellation()->save();
+        $this->invoice->fresh()->service()->handleCancellation()->save();
 
         $this->assertEquals(0, $this->invoice->fresh()->balance);
         $this->assertEquals($this->client->fresh()->balance, ($client_balance - $invoice_balance));
         $this->assertNotEquals($client_balance, $this->client->fresh()->balance);
-        $this->assertEquals(Invoice::STATUS_CANCELLED, $this->invoice->status_id);
+        $this->assertEquals(Invoice::STATUS_CANCELLED, $this->invoice->fresh()->status_id);
     }
 }
diff --git a/tests/Feature/RefundTest.php b/tests/Feature/RefundTest.php
index 1e4af1b635f4..8c33246569bf 100644
--- a/tests/Feature/RefundTest.php
+++ b/tests/Feature/RefundTest.php
@@ -14,6 +14,7 @@ use App\Factory\ClientFactory;
 use App\Factory\CreditFactory;
 use App\Factory\InvoiceFactory;
 use App\Helpers\Invoice\InvoiceSum;
+use App\Models\ClientContact;
 use App\Models\Invoice;
 use App\Models\Payment;
 use App\Utils\Traits\MakesHash;
@@ -63,6 +64,14 @@ class RefundTest extends TestCase
         $client = ClientFactory::create($this->company->id, $this->user->id);
         $client->save();
 
+        $contact = ClientContact::factory()->create([
+                'user_id' => $this->user->id,
+                'client_id' => $client->id,
+                'company_id' => $this->company->id,
+                'is_primary' => 1,
+                'send_email' => true,
+        ]);
+
         $this->invoice = InvoiceFactory::create($this->company->id, $this->user->id); //stub the company and user_id
         $this->invoice->client_id = $client->id;
         $this->invoice->status_id = Invoice::STATUS_SENT;
@@ -138,6 +147,15 @@ class RefundTest extends TestCase
         $client = ClientFactory::create($this->company->id, $this->user->id);
         $client->save();
 
+        $contact = ClientContact::factory()->create([
+                'user_id' => $this->user->id,
+                'client_id' => $client->id,
+                'company_id' => $this->company->id,
+                'is_primary' => 1,
+                'send_email' => true,
+        ]);
+
+
         $this->invoice = InvoiceFactory::create($this->company->id, $this->user->id); //stub the company and user_id
         $this->invoice->client_id = $client->id;
         $this->invoice->status_id = Invoice::STATUS_SENT;
@@ -227,6 +245,14 @@ class RefundTest extends TestCase
         $client = ClientFactory::create($this->company->id, $this->user->id);
         $client->save();
 
+        $contact = ClientContact::factory()->create([
+                'user_id' => $this->user->id,
+                'client_id' => $client->id,
+                'company_id' => $this->company->id,
+                'is_primary' => 1,
+                'send_email' => true,
+        ]);
+
         $this->invoice = InvoiceFactory::create($this->company->id, $this->user->id); //stub the company and user_id
         $this->invoice->client_id = $client->id;
         $this->invoice->status_id = Invoice::STATUS_SENT;
@@ -303,6 +329,15 @@ class RefundTest extends TestCase
         $client = ClientFactory::create($this->company->id, $this->user->id);
         $client->save();
 
+        $contact = ClientContact::factory()->create([
+                'user_id' => $this->user->id,
+                'client_id' => $client->id,
+                'company_id' => $this->company->id,
+                'is_primary' => 1,
+                'send_email' => true,
+        ]);
+
+
         $this->invoice = InvoiceFactory::create($this->company->id, $this->user->id); //stub the company and user_id
         $this->invoice->client_id = $client->id;
         $this->invoice->status_id = Invoice::STATUS_SENT;
@@ -388,6 +423,15 @@ class RefundTest extends TestCase
         $client = ClientFactory::create($this->company->id, $this->user->id);
         $client->save();
 
+        $contact = ClientContact::factory()->create([
+                'user_id' => $this->user->id,
+                'client_id' => $client->id,
+                'company_id' => $this->company->id,
+                'is_primary' => 1,
+                'send_email' => true,
+        ]);
+
+
         $this->invoice = InvoiceFactory::create($this->company->id, $this->user->id); //stub the company and user_id
         $this->invoice->client_id = $client->id;
         $this->invoice->status_id = Invoice::STATUS_SENT;
@@ -497,6 +541,15 @@ class RefundTest extends TestCase
         $client = ClientFactory::create($this->company->id, $this->user->id);
         $client->save();
 
+        $contact = ClientContact::factory()->create([
+                'user_id' => $this->user->id,
+                'client_id' => $client->id,
+                'company_id' => $this->company->id,
+                'is_primary' => 1,
+                'send_email' => true,
+        ]);
+
+
         $this->invoice = InvoiceFactory::create($this->company->id, $this->user->id); //stub the company and user_id
         $this->invoice->client_id = $client->id;
         $this->invoice->status_id = Invoice::STATUS_SENT;