diff --git a/.env.example b/.env.example
index a0a1b72e6..4dee3b334 100644
--- a/.env.example
+++ b/.env.example
@@ -37,8 +37,10 @@ MAIL_FROM=bookstack@example.com
 # SMTP mail options
 # These settings can be checked using the "Send a Test Email"
 # feature found in the "Settings > Maintenance" area of the system.
+# For more detailed documentation on mail options, refer to:
+# https://www.bookstackapp.com/docs/admin/email-webhooks/#email-configuration
 MAIL_HOST=localhost
-MAIL_PORT=1025
+MAIL_PORT=587
 MAIL_USERNAME=null
 MAIL_PASSWORD=null
 MAIL_ENCRYPTION=null
diff --git a/.env.example.complete b/.env.example.complete
index 7071846a3..96a3b448f 100644
--- a/.env.example.complete
+++ b/.env.example.complete
@@ -69,23 +69,19 @@ DB_PASSWORD=database_user_password
 # certificate itself (Common Name or Subject Alternative Name).
 MYSQL_ATTR_SSL_CA="/path/to/ca.pem"
 
-# Mail system to use
-# Can be 'smtp' or 'sendmail'
+# Mail configuration
+# Refer to https://www.bookstackapp.com/docs/admin/email-webhooks/#email-configuration
 MAIL_DRIVER=smtp
-
-# Mail sending options
 MAIL_FROM=mail@bookstackapp.com
 MAIL_FROM_NAME=BookStack
 
-# SMTP mail options
 MAIL_HOST=localhost
-MAIL_PORT=1025
+MAIL_PORT=587
 MAIL_USERNAME=null
 MAIL_PASSWORD=null
 MAIL_ENCRYPTION=null
 MAIL_VERIFY_SSL=true
 
-# Command to use when email is sent via sendmail
 MAIL_SENDMAIL_COMMAND="/usr/sbin/sendmail -bs"
 
 # Cache & Session driver to use
diff --git a/app/Config/mail.php b/app/Config/mail.php
index 87514aa40..e8ec9cc15 100644
--- a/app/Config/mail.php
+++ b/app/Config/mail.php
@@ -8,6 +8,10 @@
  * Do not edit this file unless you're happy to maintain any changes yourself.
  */
 
+// Configured mail encryption method.
+// STARTTLS should still be attempted, but tls/ssl forces TLS usage.
+$mailEncryption = env('MAIL_ENCRYPTION', null);
+
 return [
 
     // Mail driver to use.
@@ -27,9 +31,9 @@ return [
     'mailers' => [
         'smtp' => [
             'transport' => 'smtp',
+            'scheme' => ($mailEncryption === 'tls' || $mailEncryption === 'ssl') ? 'smtps' : null,
             'host' => env('MAIL_HOST', 'smtp.mailgun.org'),
             'port' => env('MAIL_PORT', 587),
-            'encryption' => env('MAIL_ENCRYPTION', 'tls'),
             'username' => env('MAIL_USERNAME'),
             'password' => env('MAIL_PASSWORD'),
             'verify_peer' => env('MAIL_VERIFY_SSL', true),
diff --git a/tests/Unit/ConfigTest.php b/tests/Unit/ConfigTest.php
index 103767516..bfd35c6b1 100644
--- a/tests/Unit/ConfigTest.php
+++ b/tests/Unit/ConfigTest.php
@@ -5,6 +5,7 @@ namespace Tests\Unit;
 use Illuminate\Support\Facades\Log;
 use Illuminate\Support\Facades\Mail;
 use Symfony\Component\Mailer\Transport\Smtp\EsmtpTransport;
+use Symfony\Component\Mailer\Transport\Smtp\Stream\SocketStream;
 use Tests\TestCase;
 
 /**
@@ -122,6 +123,45 @@ class ConfigTest extends TestCase
         });
     }
 
+    public function test_non_null_mail_encryption_options_enforce_smtp_scheme()
+    {
+        $this->checkEnvConfigResult('MAIL_ENCRYPTION', 'tls', 'mail.mailers.smtp.scheme', 'smtps');
+        $this->checkEnvConfigResult('MAIL_ENCRYPTION', 'ssl', 'mail.mailers.smtp.scheme', 'smtps');
+        $this->checkEnvConfigResult('MAIL_ENCRYPTION', 'null', 'mail.mailers.smtp.scheme', null);
+    }
+
+    public function test_smtp_scheme_and_certain_port_forces_tls_usage()
+    {
+        $isMailTlsForcedEnabled = function () {
+            $transport = Mail::mailer('smtp')->getSymfonyTransport();
+            /** @var SocketStream $stream */
+            $stream = $transport->getStream();
+            Mail::purge('smtp');
+            return $stream->isTLS();
+        };
+
+        config()->set([
+            'mail.mailers.smtp.scheme' => null,
+            'mail.mailers.smtp.port' => 587,
+        ]);
+
+        $this->assertFalse($isMailTlsForcedEnabled());
+
+        config()->set([
+            'mail.mailers.smtp.scheme' => 'smtps',
+            'mail.mailers.smtp.port' => 587,
+        ]);
+
+        $this->assertTrue($isMailTlsForcedEnabled());
+
+        config()->set([
+            'mail.mailers.smtp.scheme' => '',
+            'mail.mailers.smtp.port' => 465,
+        ]);
+
+        $this->assertTrue($isMailTlsForcedEnabled());
+    }
+
     /**
      * Set an environment variable of the given name and value
      * then check the given config key to see if it matches the given result.