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Filename : SMimeSignerTest.php
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<?php

class Swift_Signers_SMimeSignerTest extends \PHPUnit_Framework_TestCase
{
    /**
     * @var Swift_StreamFilters_StringReplacementFilterFactory
     */
    protected $replacementFactory;

    protected $samplesDir;

    protected function setUp()
    {
        $this->replacementFactory = Swift_DependencyContainer::getInstance()
            ->lookup('transport.replacementfactory');

        $this->samplesDir = str_replace('\\', '/', realpath(__DIR__.'/../../../_samples/')).'/';
    }

    public function testUnSingedMessage()
    {
        $message = Swift_SignedMessage::newInstance('Wonderful Subject')
          ->setFrom(array('john@doe.com' => 'John Doe'))
          ->setTo(array('receiver@domain.org', 'other@domain.org' => 'A name'))
          ->setBody('Here is the message itself');

        $this->assertEquals('Here is the message itself', $message->getBody());
    }

    public function testSingedMessage()
    {
        $message = Swift_SignedMessage::newInstance('Wonderful Subject')
          ->setFrom(array('john@doe.com' => 'John Doe'))
          ->setTo(array('receiver@domain.org', 'other@domain.org' => 'A name'))
          ->setBody('Here is the message itself');

        $signer = new Swift_Signers_SMimeSigner();
        $signer->setSignCertificate($this->samplesDir.'smime/sign.crt', $this->samplesDir.'smime/sign.key');
        $message->attachSigner($signer);

        $messageStream = $this->newFilteredStream();
        $message->toByteStream($messageStream);
        $messageStream->commit();

        $entityString = $messageStream->getContent();
        $headers = self::getHeadersOfMessage($entityString);

        if (!($boundary = $this->getBoundary($headers['content-type']))) {
            return false;
        }

        $expectedBody = <<<OEL
This is an S/MIME signed message

--$boundary
Content-Type: text/plain; charset=utf-8
Content-Transfer-Encoding: quoted-printable

Here is the message itself
--$boundary
Content-Type: application/(x\-)?pkcs7-signature; name="smime\.p7s"
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename="smime\.p7s"

(?:^[a-zA-Z0-9\/\\r\\n+]*={0,2})

--$boundary--
OEL;
        $this->assertValidVerify($expectedBody, $messageStream);
        unset($messageStream);
    }

    public function testSingedMessageExtraCerts()
    {
        $message = Swift_SignedMessage::newInstance('Wonderful Subject')
          ->setFrom(array('john@doe.com' => 'John Doe'))
          ->setTo(array('receiver@domain.org', 'other@domain.org' => 'A name'))
          ->setBody('Here is the message itself');

        $signer = new Swift_Signers_SMimeSigner();
        $signer->setSignCertificate($this->samplesDir.'smime/sign2.crt', $this->samplesDir.'smime/sign2.key', PKCS7_DETACHED, $this->samplesDir.'smime/intermediate.crt');
        $message->attachSigner($signer);

        $messageStream = $this->newFilteredStream();
        $message->toByteStream($messageStream);
        $messageStream->commit();

        $entityString = $messageStream->getContent();
        $headers = self::getHeadersOfMessage($entityString);

        if (!($boundary = $this->getBoundary($headers['content-type']))) {
            return false;
        }

        $expectedBody = <<<OEL
This is an S/MIME signed message

--$boundary
Content-Type: text/plain; charset=utf-8
Content-Transfer-Encoding: quoted-printable

Here is the message itself
--$boundary
Content-Type: application/(x\-)?pkcs7-signature; name="smime\.p7s"
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename="smime\.p7s"

(?:^[a-zA-Z0-9\/\\r\\n+]*={0,2})

--$boundary--
OEL;
        $this->assertValidVerify($expectedBody, $messageStream);
        unset($messageStream);
    }

    public function testSingedMessageBinary()
    {
        $message = Swift_SignedMessage::newInstance('Wonderful Subject')
          ->setFrom(array('john@doe.com' => 'John Doe'))
          ->setTo(array('receiver@domain.org', 'other@domain.org' => 'A name'))
          ->setBody('Here is the message itself');

        $signer = new Swift_Signers_SMimeSigner();
        $signer->setSignCertificate($this->samplesDir.'smime/sign.crt', $this->samplesDir.'smime/sign.key', PKCS7_BINARY);
        $message->attachSigner($signer);

        $messageStream = $this->newFilteredStream();
        $message->toByteStream($messageStream);
        $messageStream->commit();

        $entityString = $messageStream->getContent();
        $headers = self::getHeadersOfMessage($entityString);

        if (!preg_match('#^application/(x\-)?pkcs7-mime; smime-type=signed\-data;#', $headers['content-type'])) {
            $this->fail('Content-type does not match.');

            return false;
        }

        $this->assertEquals($headers['content-transfer-encoding'], 'base64');
        $this->assertEquals($headers['content-disposition'], 'attachment; filename="smime.p7m"');

        $expectedBody = '(?:^[a-zA-Z0-9\/\\r\\n+]*={0,2})';

        $messageStreamClean = $this->newFilteredStream();

        $this->assertValidVerify($expectedBody, $messageStream);
        unset($messageStreamClean, $messageStream);
    }

    public function testSingedMessageWithAttachments()
    {
        $message = Swift_SignedMessage::newInstance('Wonderful Subject')
          ->setFrom(array('john@doe.com' => 'John Doe'))
          ->setTo(array('receiver@domain.org', 'other@domain.org' => 'A name'))
          ->setBody('Here is the message itself');

        $message->attach(Swift_Attachment::fromPath($this->samplesDir.'/files/textfile.zip'));

        $signer = new Swift_Signers_SMimeSigner();
        $signer->setSignCertificate($this->samplesDir.'smime/sign.crt', $this->samplesDir.'smime/sign.key');
        $message->attachSigner($signer);

        $messageStream = $this->newFilteredStream();
        $message->toByteStream($messageStream);
        $messageStream->commit();

        $entityString = $messageStream->getContent();
        $headers = self::getHeadersOfMessage($entityString);

        if (!($boundary = $this->getBoundary($headers['content-type']))) {
            return false;
        }

        $expectedBody = <<<OEL
This is an S/MIME signed message

--$boundary
Content-Type: multipart/mixed;
 boundary="([a-z0-9\\'\\(\\)\\+_\\-,\\.\\/:=\\?\\ ]{0,69}[a-z0-9\\'\\(\\)\\+_\\-,\\.\\/:=\\?])"


--\\1
Content-Type: text/plain; charset=utf-8
Content-Transfer-Encoding: quoted-printable

Here is the message itself

--\\1
Content-Type: application/zip; name=textfile\\.zip
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename=textfile\\.zip

UEsDBAoAAgAAAMi6VjiOTiKwLgAAAC4AAAAMABUAdGV4dGZpbGUudHh0VVQJAAN3vr5Hd76\\+R1V4
BAD1AfUBVGhpcyBpcyBwYXJ0IG9mIGEgU3dpZnQgTWFpbGVyIHY0IHNtb2tlIHRlc3QuClBLAQIX
AwoAAgAAAMi6VjiOTiKwLgAAAC4AAAAMAA0AAAAAAAEAAACkgQAAAAB0ZXh0ZmlsZS50eHRVVAUA
A3e\\+vkdVeAAAUEsFBgAAAAABAAEARwAAAG0AAAAAAA==

--\\1--

--$boundary
Content-Type: application/(x\-)?pkcs7-signature; name="smime\\.p7s"
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename="smime\\.p7s"

(?:^[a-zA-Z0-9\/\\r\\n+]*={0,2})

--$boundary--
OEL;

        $this->assertValidVerify($expectedBody, $messageStream);
        unset($messageStream);
    }

    public function testEncryptedMessage()
    {
        $message = Swift_SignedMessage::newInstance('Wonderful Subject')
          ->setFrom(array('john@doe.com' => 'John Doe'))
          ->setTo(array('receiver@domain.org', 'other@domain.org' => 'A name'))
          ->setBody('Here is the message itself');

        $originalMessage = $this->cleanMessage($message->toString());

        $signer = new Swift_Signers_SMimeSigner();
        $signer->setEncryptCertificate($this->samplesDir.'smime/encrypt.crt');
        $message->attachSigner($signer);

        $messageStream = new Swift_ByteStream_TemporaryFileByteStream();
        $message->toByteStream($messageStream);
        $messageStream->commit();

        $entityString = $messageStream->getContent();
        $headers = self::getHeadersOfMessage($entityString);

        if (!preg_match('#^application/(x\-)?pkcs7-mime; smime-type=enveloped\-data;#', $headers['content-type'])) {
            $this->fail('Content-type does not match.');

            return false;
        }

        $expectedBody = '(?:^[a-zA-Z0-9\/\\r\\n+]*={0,2})';

        $decryptedMessageStream = new Swift_ByteStream_TemporaryFileByteStream();

        if (!openssl_pkcs7_decrypt($messageStream->getPath(), $decryptedMessageStream->getPath(), 'file://'.$this->samplesDir.'smime/encrypt.crt', array('file://'.$this->samplesDir.'smime/encrypt.key', 'swift'))) {
            $this->fail(sprintf('Decrypt of the message failed. Internal error "%s".', openssl_error_string()));
        }

        $this->assertEquals($originalMessage, $decryptedMessageStream->getContent());
        unset($decryptedMessageStream, $messageStream);
    }

    public function testEncryptedMessageWithMultipleCerts()
    {
        $message = Swift_SignedMessage::newInstance('Wonderful Subject')
          ->setFrom(array('john@doe.com' => 'John Doe'))
          ->setTo(array('receiver@domain.org', 'other@domain.org' => 'A name'))
          ->setBody('Here is the message itself');

        $originalMessage = $this->cleanMessage($message->toString());

        $signer = new Swift_Signers_SMimeSigner();
        $signer->setEncryptCertificate(array($this->samplesDir.'smime/encrypt.crt', $this->samplesDir.'smime/encrypt2.crt'));
        $message->attachSigner($signer);

        $messageStream = new Swift_ByteStream_TemporaryFileByteStream();
        $message->toByteStream($messageStream);
        $messageStream->commit();

        $entityString = $messageStream->getContent();
        $headers = self::getHeadersOfMessage($entityString);

        if (!preg_match('#^application/(x\-)?pkcs7-mime; smime-type=enveloped\-data;#', $headers['content-type'])) {
            $this->fail('Content-type does not match.');

            return false;
        }

        $expectedBody = '(?:^[a-zA-Z0-9\/\\r\\n+]*={0,2})';

        $decryptedMessageStream = new Swift_ByteStream_TemporaryFileByteStream();

        if (!openssl_pkcs7_decrypt($messageStream->getPath(), $decryptedMessageStream->getPath(), 'file://'.$this->samplesDir.'smime/encrypt.crt', array('file://'.$this->samplesDir.'smime/encrypt.key', 'swift'))) {
            $this->fail(sprintf('Decrypt of the message failed. Internal error "%s".', openssl_error_string()));
        }

        $this->assertEquals($originalMessage, $decryptedMessageStream->getContent());
        unset($decryptedMessageStream);

        $decryptedMessageStream = new Swift_ByteStream_TemporaryFileByteStream();

        if (!openssl_pkcs7_decrypt($messageStream->getPath(), $decryptedMessageStream->getPath(), 'file://'.$this->samplesDir.'smime/encrypt2.crt', array('file://'.$this->samplesDir.'smime/encrypt2.key', 'swift'))) {
            $this->fail(sprintf('Decrypt of the message failed. Internal error "%s".', openssl_error_string()));
        }

        $this->assertEquals($originalMessage, $decryptedMessageStream->getContent());
        unset($decryptedMessageStream, $messageStream);
    }

    public function testSignThenEncryptedMessage()
    {
        $message = Swift_SignedMessage::newInstance('Wonderful Subject')
          ->setFrom(array('john@doe.com' => 'John Doe'))
          ->setTo(array('receiver@domain.org', 'other@domain.org' => 'A name'))
          ->setBody('Here is the message itself');

        $signer = new Swift_Signers_SMimeSigner();
        $signer->setSignCertificate($this->samplesDir.'smime/sign.crt', $this->samplesDir.'smime/sign.key');
        $signer->setEncryptCertificate($this->samplesDir.'smime/encrypt.crt');
        $message->attachSigner($signer);

        $messageStream = new Swift_ByteStream_TemporaryFileByteStream();
        $message->toByteStream($messageStream);
        $messageStream->commit();

        $entityString = $messageStream->getContent();
        $headers = self::getHeadersOfMessage($entityString);

        if (!preg_match('#^application/(x\-)?pkcs7-mime; smime-type=enveloped\-data;#', $headers['content-type'])) {
            $this->fail('Content-type does not match.');

            return false;
        }

        $expectedBody = '(?:^[a-zA-Z0-9\/\\r\\n+]*={0,2})';

        $decryptedMessageStream = new Swift_ByteStream_TemporaryFileByteStream();

        if (!openssl_pkcs7_decrypt($messageStream->getPath(), $decryptedMessageStream->getPath(), 'file://'.$this->samplesDir.'smime/encrypt.crt', array('file://'.$this->samplesDir.'smime/encrypt.key', 'swift'))) {
            $this->fail(sprintf('Decrypt of the message failed. Internal error "%s".', openssl_error_string()));
        }

        $entityString = $decryptedMessageStream->getContent();
        $headers = self::getHeadersOfMessage($entityString);

        if (!($boundary = $this->getBoundary($headers['content-type']))) {
            return false;
        }

        $expectedBody = <<<OEL
This is an S/MIME signed message

--$boundary
Content-Type: text/plain; charset=utf-8
Content-Transfer-Encoding: quoted-printable

Here is the message itself
--$boundary
Content-Type: application/(x\-)?pkcs7-signature; name="smime\.p7s"
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename="smime\.p7s"

(?:^[a-zA-Z0-9\/\\r\\n+]*={0,2})

--$boundary--
OEL;

        if (!$this->assertValidVerify($expectedBody, $decryptedMessageStream)) {
            return false;
        }

        unset($decryptedMessageStream, $messageStream);
    }

    public function testEncryptThenSignMessage()
    {
        $message = Swift_SignedMessage::newInstance('Wonderful Subject')
          ->setFrom(array('john@doe.com' => 'John Doe'))
          ->setTo(array('receiver@domain.org', 'other@domain.org' => 'A name'))
          ->setBody('Here is the message itself');

        $originalMessage = $this->cleanMessage($message->toString());

        $signer = Swift_Signers_SMimeSigner::newInstance();
        $signer->setSignCertificate($this->samplesDir.'smime/sign.crt', $this->samplesDir.'smime/sign.key');
        $signer->setEncryptCertificate($this->samplesDir.'smime/encrypt.crt');
        $signer->setSignThenEncrypt(false);
        $message->attachSigner($signer);

        $messageStream = $this->newFilteredStream();
        $message->toByteStream($messageStream);
        $messageStream->commit();

        $entityString = $messageStream->getContent();
        $headers = self::getHeadersOfMessage($entityString);

        if (!($boundary = $this->getBoundary($headers['content-type']))) {
            return false;
        }

        $expectedBody = <<<OEL
This is an S/MIME signed message

--$boundary
(?P<encrypted_message>MIME-Version: 1\.0
Content-Disposition: attachment; filename="smime\.p7m"
Content-Type: application/(x\-)?pkcs7-mime; smime-type=enveloped-data; name="smime\.p7m"
Content-Transfer-Encoding: base64

(?:^[a-zA-Z0-9\/\\r\\n+]*={0,2})


)--$boundary
Content-Type: application/(x\-)?pkcs7-signature; name="smime\.p7s"
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename="smime\.p7s"

(?:^[a-zA-Z0-9\/\\r\\n+]*={0,2})

--$boundary--
OEL;

        if (!$this->assertValidVerify($expectedBody, $messageStream)) {
            return false;
        }

        $expectedBody = str_replace("\n", "\r\n", $expectedBody);
        if (!preg_match('%'.$expectedBody.'*%m', $entityString, $entities)) {
            $this->fail('Failed regex match.');

            return false;
        }

        $messageStreamClean = new Swift_ByteStream_TemporaryFileByteStream();
        $messageStreamClean->write($entities['encrypted_message']);

        $decryptedMessageStream = new Swift_ByteStream_TemporaryFileByteStream();

        if (!openssl_pkcs7_decrypt($messageStreamClean->getPath(), $decryptedMessageStream->getPath(), 'file://'.$this->samplesDir.'smime/encrypt.crt', array('file://'.$this->samplesDir.'smime/encrypt.key', 'swift'))) {
            $this->fail(sprintf('Decrypt of the message failed. Internal error "%s".', openssl_error_string()));
        }

        $this->assertEquals($originalMessage, $decryptedMessageStream->getContent());
        unset($messageStreamClean, $messageStream, $decryptedMessageStream);
    }

    protected function assertValidVerify($expected, Swift_ByteStream_TemporaryFileByteStream $messageStream)
    {
        $actual = $messageStream->getContent();

        // File is UNIX encoded so convert them to correct line ending
        $expected = str_replace("\n", "\r\n", $expected);

        $actual = trim(self::getBodyOfMessage($actual));
        if (!$this->assertRegExp('%^'.$expected.'$\s*%m', $actual)) {
            return false;
        }

        $opensslOutput = new Swift_ByteStream_TemporaryFileByteStream();
        $verify = openssl_pkcs7_verify($messageStream->getPath(), null, $opensslOutput->getPath(), array($this->samplesDir.'smime/ca.crt'));

        if (false === $verify) {
            $this->fail('Verification of the message failed.');

            return false;
        } elseif (-1 === $verify) {
            $this->fail(sprintf('Verification of the message failed. Internal error "%s".', openssl_error_string()));

            return false;
        }

        return true;
    }

    protected function getBoundary($contentType)
    {
        if (!preg_match('/boundary=("[^"]+"|(?:[^\s]+|$))/is', $contentType, $contentTypeData)) {
            $this->fail('Failed to find Boundary parameter');

            return false;
        }

        return trim($contentTypeData[1], '"');
    }

    protected function newFilteredStream()
    {
        $messageStream = new Swift_ByteStream_TemporaryFileByteStream();
        $messageStream->addFilter($this->replacementFactory->createFilter("\r\n", "\n"), 'CRLF to LF');
        $messageStream->addFilter($this->replacementFactory->createFilter("\n", "\r\n"), 'LF to CRLF');

        return $messageStream;
    }

    protected static function getBodyOfMessage($message)
    {
        return substr($message, strpos($message, "\r\n\r\n"));
    }

    /**
     * Strips of the sender headers and Mime-Version.
     *
     * @param Swift_ByteStream_TemporaryFileByteStream $messageStream
     * @param Swift_ByteStream_TemporaryFileByteStream $inputStream
     */
    protected function cleanMessage($content)
    {
        $newContent = '';

        $headers = self::getHeadersOfMessage($content);
        foreach ($headers as $headerName => $value) {
            if (!in_array($headerName, array('content-type', 'content-transfer-encoding', 'content-disposition'))) {
                continue;
            }

            $headerName = explode('-', $headerName);
            $headerName = array_map('ucfirst', $headerName);
            $headerName = implode('-', $headerName);

            if (strlen($value) > 62) {
                $value = wordwrap($value, 62, "\n ");
            }

            $newContent .= "$headerName: $value\r\n";
        }

        return $newContent."\r\n".ltrim(self::getBodyOfMessage($content));
    }

    /**
     * Returns the headers of the message.
     *
     * Header-names are lowercase.
     *
     * @param string $message
     *
     * @return array
     */
    protected static function getHeadersOfMessage($message)
    {
        $headersPosEnd = strpos($message, "\r\n\r\n");
        $headerData = substr($message, 0, $headersPosEnd);
        $headerLines = explode("\r\n", $headerData);

        if (empty($headerLines)) {
            return array();
        }

        $headers = array();

        foreach ($headerLines as $headerLine) {
            if (ctype_space($headerLines[0]) || false === strpos($headerLine, ':')) {
                $headers[$currentHeaderName] .= ' '.trim($headerLine);
                continue;
            }

            $header = explode(':', $headerLine, 2);
            $currentHeaderName = strtolower($header[0]);
            $headers[$currentHeaderName] = trim($header[1]);
        }

        return $headers;
    }
}