diff --git a/app/Ninja/Mailers/UserMailer.php b/app/Ninja/Mailers/UserMailer.php
index c509bd66afcb..8e44295cd726 100644
--- a/app/Ninja/Mailers/UserMailer.php
+++ b/app/Ninja/Mailers/UserMailer.php
@@ -58,12 +58,7 @@ class UserMailer extends Mailer
         $view = ($notificationType == 'approved' ? ENTITY_QUOTE : ENTITY_INVOICE) . "_{$notificationType}";
         $account = $user->account;
         $client = $invoice->client;
-
-        if ($account->hasMultipleAccounts()) {
-            $link = url(sprintf('/account/%s?redirect_to=%s', $account->account_key, $invoice->present()->path));
-        } else {
-            $link = $invoice->present()->url;
-        }
+        $link = $invoice->present()->multiAccountLink;
 
         $data = [
             'entityType' => $entityType,
@@ -116,6 +111,26 @@ class UserMailer extends Mailer
         $this->sendTo($user->email, CONTACT_EMAIL, CONTACT_NAME, $subject, $view, $data);
     }
 
+    /**
+     * @param Invitation $invitation
+     */
+    public function sendMessage($user, $subject, $message, $invoice)
+    {
+        if (! $user->email) {
+            return;
+        }
+
+        $view = 'user_message';
+        $data = [
+            'userName' => $user->getDisplayName(),
+            'primaryMessage' => $subject,
+            'secondaryMessage' => $message,
+            'invoiceLink' => $invoice->present()->multiAccountLink,
+        ];
+
+        $this->sendTo($user->email, CONTACT_EMAIL, CONTACT_NAME, $subject, $view, $data);
+    }
+
     public function sendSecurityCode($user, $code)
     {
         if (! $user->email) {
diff --git a/app/Ninja/Presenters/InvoicePresenter.php b/app/Ninja/Presenters/InvoicePresenter.php
index d49708e97b7d..f2a63df788de 100644
--- a/app/Ninja/Presenters/InvoicePresenter.php
+++ b/app/Ninja/Presenters/InvoicePresenter.php
@@ -279,4 +279,18 @@ class InvoicePresenter extends EntityPresenter
 
         return ' - ' . $fee . ' ' . $label;
     }
+
+    public function multiAccountLink()
+    {
+        $invoice = $this->entity;
+        $account = $invoice->account;
+
+        if ($account->hasMultipleAccounts()) {
+            $link = url(sprintf('/account/%s?redirect_to=%s', $account->account_key, $invoice->present()->path));
+        } else {
+            $link = $invoice->present()->url;
+        }
+
+        return $link;
+    }
 }
diff --git a/app/Services/PaymentService.php b/app/Services/PaymentService.php
index 1f1f54e713e6..c6e2829d298f 100644
--- a/app/Services/PaymentService.php
+++ b/app/Services/PaymentService.php
@@ -136,6 +136,13 @@ class PaymentService extends BaseService
         try {
             return $paymentDriver->completeOnsitePurchase(false, $paymentMethod);
         } catch (Exception $exception) {
+            if (! Auth::check()) {
+                $subject = trans('texts.auto_bill_failed', ['invoice_number' => $invoice->invoice_number]);
+                $message = sprintf('%s: %s', ucwords($paymentDriver->providerName()), $exception->getMessage());
+                $mailer = app('App\Ninja\Mailers\UserMailer');
+                $mailer->sendMessage($invoice->user, $subject, $message, $invoice);
+            }
+
             return false;
         }
     }
diff --git a/resources/lang/en/texts.php b/resources/lang/en/texts.php
index ad57af57901a..04ccc4789add 100644
--- a/resources/lang/en/texts.php
+++ b/resources/lang/en/texts.php
@@ -2433,6 +2433,7 @@ $LANG = array(
     'reset_counter' => 'Reset Counter',
     'next_reset' => 'Next Reset',
     'reset_counter_help' => 'Automatically reset the invoice and quote counters.',
+    'auto_bill_failed' => 'Auto-billing for invoice :invoice_number failed',
 
 );