[Mime] Added SMimeSigner and Encryptor

src/Symfony/Component/Mime/Crypto/SMime.php

@@ -0,0 +1,111 @@
+<?php
+
+/*
+ * This file is part of the Symfony package.
+ *
+ * (c) Fabien Potencier <fabien@symfony.com>
+ *
+ * For the full copyright and license information, please view the LICENSE
+ * file that was distributed with this source code.
+ */
+
+namespace Symfony\Component\Mime\Crypto;
+
+use Symfony\Component\Mime\Exception\RuntimeException;
+use Symfony\Component\Mime\Part\SMimePart;
+
+/**
+ * @author Sebastiaan Stok <s.stok@rollerscapes.net>
+ *
+ * @internal
+ */
+abstract class SMime
+{
+    protected function normalizeFilePath(string $path): string
+    {
+        if (!file_exists($path)) {
+            throw new RuntimeException(sprintf('File does not exist: %s.', $path));
+        }
+
+        return 'file://'.str_replace('\\', '/', realpath($path));
+    }
+
+    protected function iteratorToFile(iterable $iterator, $stream): void
+    {
+        foreach ($iterator as $chunk) {
+            fwrite($stream, $chunk);
+        }
+    }
+
+    protected function convertMessageToSMimePart($stream, string $type, string $subtype): SMimePart
+    {
+        rewind($stream);
+
+        $headers = '';
+
+        while (!feof($stream)) {
+            $buffer = fread($stream, 78);
+            $headers .= $buffer;
+
+            // Detect ending of header list
+            if (preg_match('/(\r\n\r\n|\n\n)/', $headers, $match)) {
+                $headersPosEnd = strpos($headers, $headerBodySeparator = $match[0]);
+
+                break;
+            }
+        }
+
+        $headers = $this->getMessageHeaders(trim(substr($headers, 0, $headersPosEnd)));
+
+        fseek($stream, $headersPosEnd + \strlen($headerBodySeparator));
+
+        return new SMimePart($this->getStreamIterator($stream), $type, $subtype, $this->getParametersFromHeader($headers['content-type']));
+    }
+
+    protected function getStreamIterator($stream): iterable
+    {
+        while (!feof($stream)) {
+            yield fread($stream, 16372);
+        }
+    }
+
+    private function getMessageHeaders(string $headerData): array
+    {
+        $headers = [];
+        $headerLines = explode("\r\n", str_replace("\n", "\r\n", str_replace("\r\n", "\n", $headerData)));
+        $currentHeaderName = '';
+
+        // Transform header lines into an associative array
+        foreach ($headerLines as $headerLine) {
+            // Empty lines between headers indicate a new mime-entity
+            if ('' === $headerLine) {
+                break;
+            }
+
+            // Handle headers that span multiple lines
+            if (false === strpos($headerLine, ':')) {
+                $headers[$currentHeaderName] .= ' '.trim($headerLine);
+                continue;
+            }
+
+            $header = explode(':', $headerLine, 2);
+            $currentHeaderName = strtolower($header[0]);
+            $headers[$currentHeaderName] = trim($header[1]);
+        }
+
+        return $headers;
+    }
+
+    private function getParametersFromHeader(string $header): array
+    {
+        $params = [];
+
+        preg_match_all('/(?P<name>[a-z-0-9]+)=(?P<value>"[^"]+"|(?:[^\s;]+|$))(?:\s+;)?/i', $header, $matches);
+
+        foreach ($matches['value'] as $pos => $paramValue) {
+            $params[$matches['name'][$pos]] = trim($paramValue, '"');
+        }
+
+        return $params;
+    }
+}

src/Symfony/Component/Mime/Crypto/SMimeEncrypter.php

@@ -0,0 +1,58 @@
+<?php
+
+/*
+ * This file is part of the Symfony package.
+ *
+ * (c) Fabien Potencier <fabien@symfony.com>
+ *
+ * For the full copyright and license information, please view the LICENSE
+ * file that was distributed with this source code.
+ */
+
+namespace Symfony\Component\Mime\Crypto;
+
+use Symfony\Component\Mime\Exception\RuntimeException;
+use Symfony\Component\Mime\Message;
+
+/**
+ * @author Sebastiaan Stok <s.stok@rollerscapes.net>
+ */
+final class SMimeEncrypter extends SMime
+{
+    private $certs;
+    private $cipher;
+
+    /**
+     * @param string|string[] $certificate Either a lone X.509 certificate, or an array of X.509 certificates
+     */
+    public function __construct($certificate, int $cipher = OPENSSL_CIPHER_AES_256_CBC)
+    {
+        if (\is_array($certificate)) {
+            $this->certs = array_map([$this, 'normalizeFilePath'], $certificate);
+        } else {
+            $this->certs = $this->normalizeFilePath($certificate);
+        }
+
+        $this->cipher = $cipher;
+    }
+
+    public function encrypt(Message $message): Message
+    {
+        $bufferFile = tmpfile();
+        $outputFile = tmpfile();
+
+        $this->iteratorToFile($message->toIterable(), $bufferFile);
+
+        if (!@openssl_pkcs7_encrypt(stream_get_meta_data($bufferFile)['uri'], stream_get_meta_data($outputFile)['uri'], $this->certs, [], 0, $this->cipher)) {
+            throw new RuntimeException(sprintf('Failed to encrypt S/Mime message. Error: "%s".', openssl_error_string()));
+        }
+
+        $mimePart = $this->convertMessageToSMimePart($outputFile, 'application', 'pkcs7-mime');
+        $mimePart->getHeaders()
+            ->addTextHeader('Content-Transfer-Encoding', 'base64')
+            ->addParameterizedHeader('Content-Disposition', 'attachment', ['name' => 'smime.p7m'])
+        ;
+
+        return new Message($message->getHeaders(), $mimePart);
+    }
+}

src/Symfony/Component/Mime/Crypto/SMimeSigner.php

@@ -0,0 +1,69 @@
+<?php
+
+/*
+ * This file is part of the Symfony package.
+ *
+ * (c) Fabien Potencier <fabien@symfony.com>
+ *
+ * For the full copyright and license information, please view the LICENSE
+ * file that was distributed with this source code.
+ */
+
+namespace Symfony\Component\Mime\Crypto;
+
+use Symfony\Component\Mime\Exception\RuntimeException;
+use Symfony\Component\Mime\Message;
+
+/**
+ * @author Sebastiaan Stok <s.stok@rollerscapes.net>
+ */
+final class SMimeSigner extends SMime
+{
+    private $signCertificate;
+    private $signPrivateKey;
+    private $signOptions;
+    private $extraCerts;
+
+    /**
+     * @var string|null
+     */
+    private $privateKeyPassphrase;
+
+    /**
+     * @see https://secure.php.net/manual/en/openssl.pkcs7.flags.php
+     *
+     * @param string      $certificate
+     * @param string      $privateKey           A file containing the private key (in PEM format)
+     * @param string|null $privateKeyPassphrase A passphrase of the private key (if any)
+     * @param string      $extraCerts           A file containing intermediate certificates (in PEM format) needed by the signing certificate
+     * @param int         $signOptions          Bitwise operator options for openssl_pkcs7_sign()
+     */
+    public function __construct(string $certificate, string $privateKey, ?string $privateKeyPassphrase = null, ?string $extraCerts = null, int $signOptions = PKCS7_DETACHED)
+    {
+        $this->signCertificate = $this->normalizeFilePath($certificate);
+
+        if (null !== $privateKeyPassphrase) {
+            $this->signPrivateKey = [$this->normalizeFilePath($privateKey), $privateKeyPassphrase];
+        } else {
+            $this->signPrivateKey = $this->normalizeFilePath($privateKey);
+        }
+
+        $this->signOptions = $signOptions;
+        $this->extraCerts = $extraCerts ? realpath($extraCerts) : null;
+        $this->privateKeyPassphrase = $privateKeyPassphrase;
+    }
+
+    public function sign(Message $message): Message
+    {
+        $bufferFile = tmpfile();
+        $outputFile = tmpfile();
+
+        $this->iteratorToFile($message->getBody()->toIterable(), $bufferFile);
+
+        if (!@openssl_pkcs7_sign(stream_get_meta_data($bufferFile)['uri'], stream_get_meta_data($outputFile)['uri'], $this->signCertificate, $this->signPrivateKey, [], $this->signOptions, $this->extraCerts)) {
+            throw new RuntimeException(sprintf('Failed to sign S/Mime message. Error: "%s".', openssl_error_string()));
+        }
+
+        return new Message($message->getHeaders(), $this->convertMessageToSMimePart($outputFile, 'multipart', 'signed'));
+    }
+}

src/Symfony/Component/Mime/Part/SMimePart.php

@@ -0,0 +1,118 @@
+<?php
+
+/*
+ * This file is part of the Symfony package.
+ *
+ * (c) Fabien Potencier <fabien@symfony.com>
+ *
+ * For the full copyright and license information, please view the LICENSE
+ * file that was distributed with this source code.
+ */
+
+namespace Symfony\Component\Mime\Part;
+
+use Symfony\Component\Mime\Header\Headers;
+
+/**
+ * @author Sebastiaan Stok <s.stok@rollerscapes.net>
+ *
+ * @experimental in 4.4
+ */
+class SMimePart extends AbstractPart
+{
+    private $body;
+    private $type;
+    private $subtype;
+    private $parameters;
+
+    /**
+     * @param iterable|string $body
+     */
+    public function __construct($body, string $type, string $subtype, array $parameters)
+    {
+        parent::__construct();
+
+        if (!\is_string($body) && !is_iterable($body)) {
+            throw new \TypeError(sprintf('The body of "%s" must be a string or a iterable (got "%s").', self::class, \is_object($body) ? \get_class($body) : \gettype($body)));
+        }
+
+        $this->body = $body;
+        $this->type = $type;
+        $this->subtype = $subtype;
+        $this->parameters = $parameters;
+    }
+
+    public function getMediaType(): string
+    {
+        return $this->type;
+    }
+
+    public function getMediaSubtype(): string
+    {
+        return $this->subtype;
+    }
+
+    public function bodyToString(): string
+    {
+        if (\is_string($this->body)) {
+            return $this->body;
+        }
+
+        $body = '';
+        foreach ($this->body as $chunk) {
+            $body .= $chunk;
+        }
+        $this->body = $body;
+
+        return $body;
+    }
+
+    public function bodyToIterable(): iterable
+    {
+        if (\is_string($this->body)) {
+            yield $this->body;
+
+            return;
+        }
+
+        $body = '';
+        foreach ($this->body as $chunk) {
+            $body .= $chunk;
+            yield $chunk;
+        }
+        $this->body = $body;
+    }
+
+    public function getPreparedHeaders(): Headers
+    {
+        $headers = clone parent::getHeaders();
+
+        $headers->setHeaderBody('Parameterized', 'Content-Type', $this->getMediaType().'/'.$this->getMediaSubtype());
+
+        foreach ($this->parameters as $name => $value) {
+            $headers->setHeaderParameter('Content-Type', $name, $value);
+        }
+
+        return $headers;
+    }
+
+    public function __sleep(): array
+    {
+        // convert iterables to strings for serialization
+        if (is_iterable($this->body)) {
+            $this->body = $this->bodyToString();
+        }
+
+        $this->_headers = $this->getHeaders();
+
+        return ['_headers', 'body', 'type', 'subtype', 'parameters'];
+    }
+
+    public function __wakeup(): void
+    {
+        $r = new \ReflectionProperty(AbstractPart::class, 'headers');
+        $r->setAccessible(true);
+        $r->setValue($this, $this->_headers);
+        unset($this->_headers);
+    }
+}

src/Symfony/Component/Mime/Tests/Crypto/SMimeEncryptorTest.php

@@ -0,0 +1,103 @@
+<?php
+
+/*
+ * This file is part of the Symfony package.
+ *
+ * (c) Fabien Potencier <fabien@symfony.com>
+ *
+ * For the full copyright and license information, please view the LICENSE
+ * file that was distributed with this source code.
+ */
+
+namespace Symfony\Component\Mime\Tests\Crypto;
+
+use Symfony\Component\Mime\Crypto\SMimeEncrypter;
+use Symfony\Component\Mime\Crypto\SMimeSigner;
+use Symfony\Component\Mime\Email;
+use Symfony\Component\Mime\Message;
+
+class SMimeEncryptorTest extends SMimeTestCase
+{
+    public function testEncryptMessage()
+    {
+        $message = (new Email())
+            ->date(new \DateTime('2019-04-07 10:36:30', new \DateTimeZone('Europe/Paris')))
+            ->to('fabien@symfony.com')
+            ->subject('Testing')
+            ->from('noreply@example.com')
+            ->text('El Barto was not here');
+
+        $message->getHeaders()->addIdHeader('Message-ID', 'some@id');
+
+        $encrypter = new SMimeEncrypter($this->samplesDir.'encrypt.crt');
+        $encryptedMessage = $encrypter->encrypt($message);
+
+        $this->assertMessageIsEncryptedProperly($encryptedMessage, $message);
+    }
+
+    public function testEncryptSignedMessage()
+    {
+        $message = (new Email())
+            ->date(new \DateTime('2019-04-07 10:36:30', new \DateTimeZone('Europe/Paris')))
+            ->to('fabien@symfony.com')
+            ->bcc('luna@symfony.com')
+            ->subject('Testing')
+            ->from('noreply@example.com')
+            ->text('El Barto was not here');
+
+        $message->getHeaders()->addIdHeader('Message-ID', 'some@id');
+
+        $signer = new SMimeSigner($this->samplesDir.'sign.crt', $this->samplesDir.'sign.key');
+        $signedMessage = $signer->sign($message);
+
+        $encrypter = new SMimeEncrypter($this->samplesDir.'encrypt.crt');
+        $encryptedMessage = $encrypter->encrypt($signedMessage);
+
+        $this->assertMessageIsEncryptedProperly($encryptedMessage, $signedMessage);
+    }
+
+    public function testEncryptMessageWithMultipleCerts()
+    {
+        $message = (new Email())
+            ->date(new \DateTime('2019-04-07 10:36:30', new \DateTimeZone('Europe/Paris')))
+            ->to('fabien@symfony.com')
+            ->subject('Testing')
+            ->from('noreply@example.com')
+            ->text('El Barto was not here');
+
+        $message2 = (new Email())
+            ->date(new \DateTime('2019-04-07 10:36:30', new \DateTimeZone('Europe/Paris')))
+            ->to('luna@symfony.com')
+            ->subject('Testing')
+            ->from('noreply@example.com')
+            ->text('El Barto was not here');
+
+        $message->getHeaders()->addIdHeader('Message-ID', 'some@id');
+        $message2->getHeaders()->addIdHeader('Message-ID', 'some@id2');
+
+        $encrypter = new SMimeEncrypter(['fabien@symfony.com' => $this->samplesDir.'encrypt.crt', 'luna@symfony.com' => $this->samplesDir.'encrypt2.crt']);
+
+        $this->assertMessageIsEncryptedProperly($encrypter->encrypt($message), $message);
+        $this->assertMessageIsEncryptedProperly($encrypter->encrypt($message2), $message2);
+    }
+
+    private function assertMessageIsEncryptedProperly(Message $message, Message $originalMessage): void
+    {
+        $messageFile = $this->generateTmpFilename();
+        file_put_contents($messageFile, $message->toString());
+
+        $outputFile = $this->generateTmpFilename();
+
+        $this->assertMessageHeaders($message, $originalMessage);
+        $this->assertTrue(
+            openssl_pkcs7_decrypt(
+                $messageFile,
+                $outputFile,
+                'file://'.$this->samplesDir.'encrypt.crt',
+                'file://'.$this->samplesDir.'encrypt.key'
+            ),
+            sprintf('Decryption of the message failed. Internal error "%s".', openssl_error_string())
+        );
+        $this->assertEquals(str_replace("\r", '', $originalMessage->toString()), str_replace("\r", '', file_get_contents($outputFile)));
+    }
+}

src/Symfony/Component/Mime/Tests/Crypto/SMimeSignerTest.php

@@ -0,0 +1,163 @@
+<?php
+
+/*
+ * This file is part of the Symfony package.
+ *
+ * (c) Fabien Potencier <fabien@symfony.com>
+ *
+ * For the full copyright and license information, please view the LICENSE
+ * file that was distributed with this source code.
+ */
+
+namespace Symfony\Component\Mime\Tests\Crypto;
+
+use Symfony\Component\Mime\Crypto\SMimeEncrypter;
+use Symfony\Component\Mime\Crypto\SMimeSigner;
+use Symfony\Component\Mime\Email;
+use Symfony\Component\Mime\Header\Headers;
+use Symfony\Component\Mime\Message;
+use Symfony\Component\Mime\Part\TextPart;
+
+class SMimeSignerTest extends SMimeTestCase
+{
+    public function testSignedMessage()
+    {
+        $message = new Message(
+            (new Headers())
+                ->addDateHeader('Date', new \DateTime('2019-04-07 10:36:30', new \DateTimeZone('Europe/Paris')))
+                ->addMailboxListHeader('From', ['fabien@symfony.com']),
+            new TextPart('content')
+        );
+
+        $signer = new SMimeSigner($this->samplesDir.'sign.crt', $this->samplesDir.'sign.key');
+        $signedMessage = $signer->sign($message);
+
+        $this->assertMessageSignatureIsValid($signedMessage, $message);
+    }
+
+    public function testSignEncryptedMessage()
+    {
+        $message = (new Email())
+            ->date(new \DateTime('2019-04-07 10:36:30', new \DateTimeZone('Europe/Paris')))
+            ->to('fabien@symfony.com')
+            ->subject('Testing')
+            ->from('noreply@example.com')
+            ->text('El Barto was not here');
+
+        $message->getHeaders()->addIdHeader('Message-ID', 'some@id');
+
+        $encrypter = new SMimeEncrypter($this->samplesDir.'encrypt.crt');
+        $encryptedMessage = $encrypter->encrypt($message);
+
+        $signer = new SMimeSigner($this->samplesDir.'sign.crt', $this->samplesDir.'sign.key');
+        $signedMessage = $signer->sign($encryptedMessage);
+
+        $this->assertMessageSignatureIsValid($signedMessage, $message);
+    }
+
+    public function testSignedMessageWithPassphrase()
+    {
+        $message = new Message(
+            (new Headers())
+                ->addDateHeader('Date', new \DateTime('2019-04-07 10:36:30', new \DateTimeZone('Europe/Paris')))
+                ->addMailboxListHeader('From', ['fabien@symfony.com']),
+            new TextPart('content')
+        );
+
+        $signer = new SMimeSigner($this->samplesDir.'sign3.crt', $this->samplesDir.'sign3.key', 'symfony-rocks');
+        $signedMessage = $signer->sign($message);
+
+        $this->assertMessageSignatureIsValid($signedMessage, $message);
+    }
+
+    public function testProperSerialiable()
+    {
+        $message = (new Email())
+            ->date(new \DateTime('2019-04-07 10:36:30', new \DateTimeZone('Europe/Paris')))
+            ->to('fabien@symfony.com')
+            ->subject('Testing')
+            ->from('noreply@example.com')
+            ->text('El Barto was not here');
+
+        $message->getHeaders()->addIdHeader('Message-ID', 'some@id');
+
+        $signer = new SMimeSigner($this->samplesDir.'sign.crt', $this->samplesDir.'sign.key');
+        $signedMessage = $signer->sign($message);
+
+        $restoredMessage = unserialize(serialize($signedMessage));
+
+        self::assertSame($this->iterableToString($signedMessage->toIterable()), $this->iterableToString($restoredMessage->toIterable()));
+        self::assertSame($signedMessage->toString(), $restoredMessage->toString());
+
+        $this->assertMessageSignatureIsValid($restoredMessage, $message);
+    }
+
+    public function testSignedMessageWithBcc()
+    {
+        $message = (new Email())
+            ->date(new \DateTime('2019-04-07 10:36:30', new \DateTimeZone('Europe/Paris')))
+            ->addBcc('fabien@symfony.com', 's.stok@rollerscapes.net')
+            ->subject('I am your sign of fear')
+            ->from('noreply@example.com')
+            ->text('El Barto was not here');
+
+        $signer = new SMimeSigner($this->samplesDir.'sign.crt', $this->samplesDir.'sign.key');
+        $signedMessage = $signer->sign($message);
+
+        $this->assertMessageSignatureIsValid($signedMessage, $message);
+    }
+
+    public function testSignedMessageWithAttachments()
+    {
+        $message = new Email((new Headers())
+            ->addDateHeader('Date', new \DateTime('2019-04-07 10:36:30', new \DateTimeZone('Europe/Paris')))
+            ->addMailboxListHeader('From', ['fabien@symfony.com'])
+        );
+        $message->html($content = 'html content <img src="cid:test.gif">');
+        $message->text('text content');
+        $message->attach(fopen(__DIR__.'/../Fixtures/mimetypes/test', 'r'));
+        $message->attach(fopen(__DIR__.'/../Fixtures/mimetypes/test.gif', 'r'), 'test.gif');
+
+        $signer = new SMimeSigner($this->samplesDir.'sign.crt', $this->samplesDir.'sign.key');
+
+        $signedMessage = $signer->sign($message);
+        $this->assertMessageSignatureIsValid($signedMessage, $message);
+    }
+
+    public function testSignedMessageExtraCerts()
+    {
+        $message = new Message(
+            (new Headers())
+                ->addDateHeader('Date', new \DateTime('2019-04-07 10:36:30', new \DateTimeZone('Europe/Paris')))
+                ->addMailboxListHeader('From', ['fabien@symfony.com']),
+            new TextPart('content')
+        );
+
+        $signer = new SMimeSigner(
+            $this->samplesDir.'sign.crt',
+            $this->samplesDir.'sign.key',
+            null,
+            $this->samplesDir.'intermediate.crt',
+            PKCS7_DETACHED
+        );
+        $signedMessage = $signer->sign($message);
+
+        $this->assertMessageSignatureIsValid($signedMessage, $message);
+    }
+
+    private function assertMessageSignatureIsValid(Message $message, Message $originalMessage): void
+    {
+        $messageFile = $this->generateTmpFilename();
+        $messageString = $message->toString();
+        file_put_contents($messageFile, $messageString);
+
+        $this->assertMessageHeaders($message, $originalMessage);
+        $this->assertTrue(openssl_pkcs7_verify($messageFile, 0, $this->generateTmpFilename(), [$this->samplesDir.'ca.crt']), sprintf('Verification of the message %s failed. Internal error "%s".', $messageFile, openssl_error_string()));
+
+        if (false === strpos($messageString, 'enveloped-data')) {
+            // Tamper to ensure it actually verified
+            file_put_contents($messageFile, str_replace('Content-Transfer-Encoding: ', 'Content-Transfer-Encoding:  ', $messageString));
+            $this->assertFalse(openssl_pkcs7_verify($messageFile, 0, $this->generateTmpFilename(), [$this->samplesDir.'ca.crt']), sprintf('Verification of the message failed. Internal error "%s".', openssl_error_string()));
+        }
+    }
+}

src/Symfony/Component/Mime/Tests/Crypto/SMimeTestCase.php

@@ -0,0 +1,73 @@
+<?php
+
+/*
+ * This file is part of the Symfony package.
+ *
+ * (c) Fabien Potencier <fabien@symfony.com>
+ *
+ * For the full copyright and license information, please view the LICENSE
+ * file that was distributed with this source code.
+ */
+
+namespace Symfony\Component\Mime\Tests\Crypto;
+
+use PHPUnit\Framework\TestCase;
+use Symfony\Component\Mime\Exception\RuntimeException;
+use Symfony\Component\Mime\Message;
+use Symfony\Component\Mime\RawMessage;
+
+abstract class SMimeTestCase extends TestCase
+{
+    protected $samplesDir;
+
+    protected function setUp(): void
+    {
+        $this->samplesDir = str_replace('\\', '/', realpath(__DIR__.'/../').'/_data/');
+    }
+
+    protected function generateTmpFilename(): string
+    {
+        return stream_get_meta_data(tmpfile())['uri'];
+    }
+
+    protected function normalizeFilePath(string $path): string
+    {
+        if (!file_exists($path)) {
+            throw new RuntimeException(sprintf('File does not exist: %s', $path));
+        }
+
+        return str_replace('\\', '/', realpath($path));
+    }
+
+    protected function iterableToString(iterable $iterable): string
+    {
+        $string = '';
+
+        // Can't use iterator_to_array as the generators are merged internally,
+        // leading to overwritten keys
+        foreach ($iterable as $chunk) {
+            $string .= $chunk;
+        }
+
+        return $string;
+    }
+
+    protected function assertMessageHeaders(Message $message, RawMessage $originalMessage): void
+    {
+        $messageString = $message->toString();
+        self::assertNotContains('Bcc: ', $messageString, '', true);
+
+        if (!$originalMessage instanceof Message) {
+            return;
+        }
+
+        if ($originalMessage->getHeaders()->has('Bcc')) {
+            self::assertEquals($originalMessage->getHeaders()->get('Bcc'), $message->getHeaders()->get('Bcc'));
+        }
+
+        if ($originalMessage->getHeaders()->has('Subject')) {
+            self::assertEquals($originalMessage->getHeaders()->get('Subject'), $message->getPreparedHeaders()->get('Subject'));
+            self::assertContains('Subject:', $messageString, '', true);
+        }
+    }
+}

src/Symfony/Component/Mime/Tests/_data/ca.crt

@@ -0,0 +1,19 @@
+-----BEGIN CERTIFICATE-----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+4C5LZtdWzhons4jOmtmxaMSy08oPPYv1wXATjjfHvqqYa/7axLY1mqbxLYC437Fv
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+NFxckxTgT4ylmivmHZWym4xS1bkAAAsd
+-----END CERTIFICATE-----

src/Symfony/Component/Mime/Tests/_data/ca.key

@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----
+MIIEowIBAAKCAQEAnvxOWE8qOVkuYbTu6u4Oao2n91FPF6umrcF8mq0uD2G0dtOJ
+uFaR7FeElmJnHfWvqvesCigXyA7kpdVBFGhEo83SGYTbPSGzehWDc7Kvc321UPvN
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+MxHrYi2bgkhxVoAY03ZQRbb95rEE1cfyGZ0x6VSBrVC2nnEUT2vopwny/vy+QSn3
+oga+ucMkxJdoD8MA13Zh5I4Uiozl82xoWH/zmVrqrrO2lNBv7WYOnwbv6MSr5kCE
+3Kcqzs8qAGv62GYyS4exIMEZsbbPv3cvp9hgYQIDAQABAoIBAD/Y1WGzkSJsxSqp
+7dTc+18hOlYhCiFYZtyaun6nk7rLoxyhQUqNQZbnYrC+HekzNHP1eNqvVTWbfYl3
+heY7JW2fB4QGDcGUGi6qGxtIpBs+XaWDKfJyahyO6F9gLnGoR5wphKnh6thj+ggA
+Vciq76w7yDfzWqoK+++d2ao/JkDg7YrpOQonfceYgjTtiXXFDV4cm4GgKr7gWolt
+AqZbHcbH6pmbwRduT+g5QjsYmYPven/ji6Mr2eTFwE0qjlwj4LHlEWuKgpwAnLc/
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+S0zUeh/qA600bxraqi6WUkuwS/5IeUwkSPwZUpuYzWZU/mVD+XNjTu2XJFr+Cuch
+I6tAb6nfM/ESO6Oj4oqyCxECgYBsXr4iF1UPQ3OOmoKtMnZJVVejjcJxbSNkK4LS
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+2yYN83Sr8oeZv81X0ReoHsyTgN4PYSI70HJf/YEKsBA8JyjJ25QFEAI27bZyQzc7
+m72/RQKBgEtyibh8X7DC9B3oVMZAX1BJJDzDSH1RyRaoa+7nARSl90qJD877NZ8o
+jteoRFNJJzruADouffK+lTlMtwdfQJQW4wGYGiyr1S5dKXNsPmcnKCj7HbvBphVA
+oCzZi3txFcOmH4IZ5HA0VxvGViQwV7fyl5ch7XVqSFOeFaa6lIF5
+-----END RSA PRIVATE KEY-----

src/Symfony/Component/Mime/Tests/_data/ca.srl

@@ -0,0 +1 @@
+C51E36445BB0C79B

src/Symfony/Component/Mime/Tests/_data/create-cert.sh

@@ -0,0 +1,52 @@
+#!/bin/sh
+
+openssl genrsa -out ca.key 2048
+openssl req -x509 -new -nodes -key ca.key -days 1460 -subj '/CN=SymfonyMime CA/O=SymfonyMime/L=Paris/C=FR' -out ca.crt
+openssl x509 -in ca.crt -clrtrust -out ca.crt
+
+## Sign
+
+openssl genrsa -out sign.key 2048
+openssl req -new -key sign.key -subj '/CN=fabien@symfony.com/O=SymfonyMime/L=Paris/C=FR/emailAddress=fabien@symfony.com' -out sign.csr
+openssl x509 -req -in sign.csr -CA ca.crt -CAkey ca.key -out sign.crt -days 1460 -addtrust emailProtection
+openssl x509 -in sign.crt -clrtrust -out sign.crt
+
+rm sign.csr
+
+openssl genrsa -out intermediate.key 2048
+openssl req -new -key intermediate.key -subj '/CN=SymfonyMime Intermediate/O=SymfonyMime/L=Paris/C=FR' -out intermediate.csr
+openssl x509 -req -in intermediate.csr -CA ca.crt -CAkey ca.key -set_serial 01 -out intermediate.crt -days 1460
+openssl x509 -in intermediate.crt -clrtrust -out intermediate.crt
+
+rm intermediate.csr
+
+openssl genrsa -out sign2.key 2048
+openssl req -new -key sign2.key -subj '/CN=SymfonyMime-User2/O=SymfonyMime/L=Paris/C=FR' -out sign2.csr
+openssl x509 -req -in sign2.csr -CA intermediate.crt -CAkey intermediate.key -set_serial 01 -out sign2.crt -days 1460 -addtrust emailProtection
+openssl x509 -in sign2.crt -clrtrust -out sign2.crt
+
+rm sign2.csr
+
+### Sign with passphrase
+openssl genrsa -aes256 -passout pass:symfony-rocks -out sign3.key 2048
+openssl req -new -key sign3.key -passin pass:symfony-rocks -subj '/CN=SymfonyMime-User3/O=SymfonyMime/L=Paris/C=FR' -out sign3.csr
+openssl x509 -req -in sign3.csr -CA ca.crt -CAkey ca.key -out sign3.crt -days 1460 -addtrust emailProtection
+openssl x509 -in sign3.crt -clrtrust -out sign3.crt
+
+rm sign3.csr
+
+## Encrypt
+
+openssl genrsa -out encrypt.key 2048
+openssl req -new -key encrypt.key -subj '/CN=SymfonyMime-User/O=SymfonyMime/L=Paris/C=FR' -out encrypt.csr
+openssl x509 -req -in encrypt.csr -CA ca.crt -CAkey ca.key -CAcreateserial -out encrypt.crt -days 1460 -addtrust emailProtection
+openssl x509 -in encrypt.crt -clrtrust -out encrypt.crt
+
+rm encrypt.csr
+
+openssl genrsa -out encrypt2.key 2048
+openssl req -new -key encrypt2.key -subj '/CN=SymfonyMime-User2/O=SymfonyMime/L=Paris/C=FR' -out encrypt2.csr
+openssl x509 -req -in encrypt2.csr -CA ca.crt -CAkey ca.key -CAcreateserial -out encrypt2.crt -days 1460 -addtrust emailProtection
+openssl x509 -in encrypt2.crt -clrtrust -out encrypt2.crt
+
+rm encrypt2.csr

src/Symfony/Component/Mime/Tests/_data/encrypt.crt

@@ -0,0 +1,19 @@
+-----BEGIN CERTIFICATE-----
+MIIDFjCCAf4CCQDFHjZEW7DHmjANBgkqhkiG9w0BAQUFADBMMRcwFQYDVQQDDA5T
+eW1mb255TWltZSBDQTEUMBIGA1UECgwLU3ltZm9ueU1pbWUxDjAMBgNVBAcMBVBh
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+KpZ7PMSJTC+bJYl3KVoIjBJ9/Bf1yjygb38=
+-----END CERTIFICATE-----

src/Symfony/Component/Mime/Tests/_data/encrypt.key

@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----
+MIIEowIBAAKCAQEAsZzE9UxploQaeCuiCs7YqZSlbHaGL4vCbH5U6QR4sP7Swd4p
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+-----END RSA PRIVATE KEY-----

src/Symfony/Component/Mime/Tests/_data/encrypt2.crt

@@ -0,0 +1,19 @@
+-----BEGIN CERTIFICATE-----
+MIIDFzCCAf8CCQDFHjZEW7DHmzANBgkqhkiG9w0BAQUFADBMMRcwFQYDVQQDDA5T
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+oFHODRxroV7eu+L2fQMmHtcbXKCTWg7lfvgW
+-----END CERTIFICATE-----

src/Symfony/Component/Mime/Tests/_data/encrypt2.key

@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----
+MIIEowIBAAKCAQEAvGX70bC9IIjPKIGN3FKR3wNHD5UdXhgEWpMDuQeAgZ01LRc+
+tTactRMsuI3lTXCGOmU+kXpT03GcUEB4sP4ykSw04umDn8UbZ0o9WfzW8c2Es3iY
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+hPaPjrm2jSDBdaHlO/wFUq2Oo8hSlWrqHiUCTLg/TfkGegYL+RUc
+-----END RSA PRIVATE KEY-----

src/Symfony/Component/Mime/Tests/_data/intermediate.crt

@@ -0,0 +1,19 @@
+-----BEGIN CERTIFICATE-----
+MIIDFjCCAf4CAQEwDQYJKoZIhvcNAQEFBQAwTDEXMBUGA1UEAwwOU3ltZm9ueU1p
+bWUgQ0ExFDASBgNVBAoMC1N5bWZvbnlNaW1lMQ4wDAYDVQQHDAVQYXJpczELMAkG
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+-----END CERTIFICATE-----

src/Symfony/Component/Mime/Tests/_data/intermediate.key

@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----
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+-----END RSA PRIVATE KEY-----

src/Symfony/Component/Mime/Tests/_data/sign.crt

@@ -0,0 +1,20 @@
+-----BEGIN CERTIFICATE-----
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src/Symfony/Component/Mime/Tests/_data/sign.key

@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----
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+-----END RSA PRIVATE KEY-----

src/Symfony/Component/Mime/Tests/_data/sign2.crt

@@ -0,0 +1,19 @@
+-----BEGIN CERTIFICATE-----
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src/Symfony/Component/Mime/Tests/_data/sign2.key

@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----
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+-----END RSA PRIVATE KEY-----

src/Symfony/Component/Mime/Tests/_data/sign3.crt

@@ -0,0 +1,19 @@
+-----BEGIN CERTIFICATE-----
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src/Symfony/Component/Mime/Tests/_data/sign3.key

@@ -0,0 +1,30 @@
+-----BEGIN RSA PRIVATE KEY-----
+Proc-Type: 4,ENCRYPTED
+DEK-Info: AES-256-CBC,5485FF78699F76CB93A05FF9CE7FB4FD
+
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+-----END RSA PRIVATE KEY-----