From 1f6c6140bafd499f4af42b8d77ae16ae58a1ab88 Mon Sep 17 00:00:00 2001
From: peaklabs-dev <122374094+peaklabs-dev@users.noreply.github.com>
Date: Mon, 23 Dec 2024 15:28:35 +0100
Subject: [PATCH] fix: smtp encryption

---
 app/Notifications/Channels/EmailChannel.php | 11 +++++++++--
 bootstrap/helpers/notifications.php         | 11 ++++++++++-
 2 files changed, 19 insertions(+), 3 deletions(-)

diff --git a/app/Notifications/Channels/EmailChannel.php b/app/Notifications/Channels/EmailChannel.php
index 0985f43933..6ffe5c4d79 100644
--- a/app/Notifications/Channels/EmailChannel.php
+++ b/app/Notifications/Channels/EmailChannel.php
@@ -66,17 +66,24 @@ private function bootConfigs($notifiable): void
         }
 
         if ($emailSettings->smtp_enabled) {
+            $encryption = match (strtolower($emailSettings->smtp_encryption)) {
+                'starttls' => null,
+                'tls' => 'tls',
+                'none' => null,
+                default => null,
+            };
+
             config()->set('mail.default', 'smtp');
             config()->set('mail.mailers.smtp', [
                 'transport' => 'smtp',
                 'host' => $emailSettings->smtp_host,
                 'port' => $emailSettings->smtp_port,
-                'encryption' => $emailSettings->smtp_encryption === 'none' ? null : $emailSettings->smtp_encryption,
+                'encryption' => $encryption,
                 'username' => $emailSettings->smtp_username,
                 'password' => $emailSettings->smtp_password,
                 'timeout' => $emailSettings->smtp_timeout,
                 'local_domain' => null,
-                'auto_tls' => $emailSettings->smtp_encryption === 'none' ? '0' : '',
+                'auto_tls' => $emailSettings->smtp_encryption === 'none' ? '0' : '', // If encryption is "none", it will not try to upgrade to TLS via StartTLS to make sure it is unencrypted.
             ]);
         }
     }
diff --git a/bootstrap/helpers/notifications.php b/bootstrap/helpers/notifications.php
index 3b1eb758b8..46f0ebca76 100644
--- a/bootstrap/helpers/notifications.php
+++ b/bootstrap/helpers/notifications.php
@@ -67,17 +67,26 @@ function set_transanctional_email_settings(?InstanceSettings $settings = null):
 
         return 'resend';
     }
+
+    $encryption = match (strtolower(data_get($settings, 'smtp_encryption'))) {
+        'starttls' => null,
+        'tls' => 'tls',
+        'none' => null,
+        default => null,
+    };
+
     if (data_get($settings, 'smtp_enabled')) {
         config()->set('mail.default', 'smtp');
         config()->set('mail.mailers.smtp', [
             'transport' => 'smtp',
             'host' => data_get($settings, 'smtp_host'),
             'port' => data_get($settings, 'smtp_port'),
-            'encryption' => data_get($settings, 'smtp_encryption'),
+            'encryption' => $encryption,
             'username' => data_get($settings, 'smtp_username'),
             'password' => data_get($settings, 'smtp_password'),
             'timeout' => data_get($settings, 'smtp_timeout'),
             'local_domain' => null,
+            'auto_tls' => data_get($settings, 'smtp_encryption') === 'none' ? '0' : '', // If encryption is "none", it will not try to upgrade to TLS via StartTLS to make sure it is unencrypted.
         ]);
 
         return 'smtp';