From 71d207ed9baddde8a9f38f565497d8c74ae300fd Mon Sep 17 00:00:00 2001
From: Rico Kritz <>
Date: Fri, 22 May 2026 14:34:13 +0200
Subject: [PATCH] added tests for sending encrypted emails and ensure mailer
 and mime assertions can handle Message objects as well

---
 composer.json                                 |  1 +
 config/routes.php                             |  4 ++
 .../SendEncryptedEmailController.php          | 25 +++++++++++++
 src/Utils/Crypto.php                          | 37 +++++++++++++++++++
 src/Utils/Mailer.php                          | 25 ++++++++++++-
 tests/Functional/IssuesCest.php               | 14 +++++++
 6 files changed, 104 insertions(+), 2 deletions(-)
 create mode 100644 src/Controller/SendEncryptedEmailController.php
 create mode 100644 src/Utils/Crypto.php

diff --git a/composer.json b/composer.json
index c2087fa..d1353f9 100644
--- a/composer.json
+++ b/composer.json
@@ -31,6 +31,7 @@
         "symfony/yaml": "5.4.*"
     },
     "require-dev": {
+        "ext-openssl": "*",
         "codeception/codeception": "^5.3",
         "codeception/module-asserts": "^3.2",
         "codeception/module-doctrine": "^3.3",
diff --git a/config/routes.php b/config/routes.php
index 0446a1a..3e4bd8a 100644
--- a/config/routes.php
+++ b/config/routes.php
@@ -88,4 +88,8 @@
     $routes->add('send_email', '/send-email')
         ->controller(App\Controller\SendEmailController::class)
         ->methods(['GET']);
+
+    $routes->add('send_encrypted_email', '/send-encrypted-email')
+        ->controller(App\Controller\SendEncryptedEmailController::class)
+        ->methods(['GET']);
 };
diff --git a/src/Controller/SendEncryptedEmailController.php b/src/Controller/SendEncryptedEmailController.php
new file mode 100644
index 0000000..032b912
--- /dev/null
+++ b/src/Controller/SendEncryptedEmailController.php
@@ -0,0 +1,25 @@
+<?php
+
+declare(strict_types=1);
+
+namespace App\Controller;
+
+use App\Entity\User;
+use App\Utils\Mailer;
+use Symfony\Bundle\FrameworkBundle\Controller\AbstractController;
+use Symfony\Component\HttpFoundation\Response;
+
+final class SendEncryptedEmailController extends AbstractController
+{
+    public function __construct(
+        private readonly Mailer $mailer,
+    ) {
+    }
+
+    public function __invoke(): Response
+    {
+        $this->mailer->sendEncryptedEmail((new User())->setEmail('jane_doe@example.com'));
+
+        return $this->json(['message' => 'Encrypted email sent successfully']);
+    }
+}
diff --git a/src/Utils/Crypto.php b/src/Utils/Crypto.php
new file mode 100644
index 0000000..1c7683d
--- /dev/null
+++ b/src/Utils/Crypto.php
@@ -0,0 +1,37 @@
+<?php
+
+declare(strict_types=1);
+
+namespace App\Utils;
+
+final readonly class Crypto
+{
+    public function generateSslCertificate(): string
+    {
+        if (!extension_loaded('openssl')) {
+            throw new \RuntimeException('OpenSSL extension is required.');
+        }
+
+        $privateKey = openssl_pkey_new();
+        $certSignRequest = openssl_csr_new([], $privateKey);
+        $certificate = openssl_csr_sign($certSignRequest, null, $privateKey, 1);
+
+        $tmpDir = sys_get_temp_dir();
+        $privateKeyPath = tempnam($tmpDir, 'pkey');
+        $certificatePath = tempnam($tmpDir, 'cert');
+
+        if (!openssl_pkey_export_to_file($privateKey, $privateKeyPath, 'powercloud')) {
+            throw new \RuntimeException('Private key generation failed: ' . openssl_error_string());
+        }
+        if (!openssl_x509_export_to_file($certificate, $certificatePath)) {
+            throw new \RuntimeException('OpenSSL certificate generation failed: ' . openssl_error_string());
+        }
+
+        register_shutdown_function(static function () use ($privateKeyPath, $certificatePath): void {
+            unlink($privateKeyPath);
+            unlink($certificatePath);
+        });
+
+        return $certificatePath;
+    }
+}
diff --git a/src/Utils/Mailer.php b/src/Utils/Mailer.php
index 5412990..ea2e242 100644
--- a/src/Utils/Mailer.php
+++ b/src/Utils/Mailer.php
@@ -8,11 +8,16 @@
 use Symfony\Bridge\Twig\Mime\TemplatedEmail;
 use Symfony\Component\Mailer\MailerInterface;
 use Symfony\Component\Mime\Address;
+use Symfony\Component\Mime\Crypto\SMimeEncrypter;
+use Symfony\Component\Mime\Email;
+use Symfony\Component\Mime\Message;
 
 final readonly class Mailer
 {
-    public function __construct(private MailerInterface $mailer)
-    {
+    public function __construct(
+        private MailerInterface $mailer,
+        private Crypto $crypto,
+    ) {
     }
 
     public function sendConfirmationEmail(User $user): TemplatedEmail
@@ -30,4 +35,20 @@ public function sendConfirmationEmail(User $user): TemplatedEmail
 
         return $email;
     }
+
+    public function sendEncryptedEmail(User $user): Message
+    {
+        $encrypter = new SMimeEncrypter($this->crypto->generateSslCertificate());
+
+        $email = (new Email())
+            ->from(new Address('jeison_doe@gmail.com', 'No Reply'))
+            ->to(new Address($user->getEmail()))
+            ->subject('Encrypted email')
+            ->text('Encrypted content');
+
+        $message = $encrypter->encrypt($email);
+        $this->mailer->send($message);
+
+        return $message;
+    }
 }
diff --git a/tests/Functional/IssuesCest.php b/tests/Functional/IssuesCest.php
index 433b991..97908cb 100644
--- a/tests/Functional/IssuesCest.php
+++ b/tests/Functional/IssuesCest.php
@@ -7,6 +7,7 @@
 use App\Entity\User;
 use App\Tests\Support\FunctionalTester;
 use Doctrine\DBAL\Connection;
+use Symfony\Component\Mime\Message;
 
 final class IssuesCest
 {
@@ -53,4 +54,17 @@ public function runSymfonyConsoleCommandIgnoresSpecificOptions(FunctionalTester
         $numRecords = $I->grabNumRecords(User::class);
         $I->assertSame(1, $numRecords);
     }
+
+    /**
+     * @see https://github.com/Codeception/module-symfony/pull/232
+     */
+    public function assertEncryptedEmailTests(FunctionalTester $I)
+    {
+        $I->amOnPage('/send-encrypted-email');
+        $I->seeEmailIsSent(1);
+        $I->assertEmailAddressContains('To', 'jane_doe@example.com');
+        $I->assertEmailHeaderSame('To', 'jane_doe@example.com');
+        $I->assertEmailHeaderSame('Subject', 'Encrypted email');
+        $I->assertInstanceOf(Message::class, $I->grabLastSentEmail());
+    }
 }