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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 testUnSignedMessage()
{
$message = (new Swift_Message('Wonderful Subject'))
->setFrom(['john@doe.com' => 'John Doe'])
->setTo(['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 testSignedMessage()
{
$message = (new Swift_Message('Wonderful Subject'))
->setFrom(['john@doe.com' => 'John Doe'])
->setTo(['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 testSignedMessageWithFullyWrappedMessage()
{
$message = (new Swift_Message('Middle-out compression secrets'))
->setFrom(['richard@piedpiper.com' => 'Richard Hendricks'])
->setTo(['jared@piedpiper.com' => 'Jared Dunn'])
->setBody('Here goes the entire algorithm...');
$signer = new Swift_Signers_SMimeSigner();
$signer->setSignCertificate($this->samplesDir.'smime/sign.crt', $this->samplesDir.'smime/sign.key');
// Tell the signer to wrap the full MIME message
$signer->setWrapFullMessage(true);
$message->attachSigner($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: message/rfc822; charset=utf-8
Content-Transfer-Encoding: 7bit
Message-ID: <[a-f0-9]+@swift.generated>
Date: .*
Subject: Middle-out compression secrets
From: Richard Hendricks <richard@piedpiper.com>
To: Jared Dunn <jared@piedpiper.com>
MIME-Version: 1.0
Content-Type: text/plain; charset=utf-8
Content-Transfer-Encoding: quoted-printable
Here goes the entire algorithm...
--$boundary
Content-Type: application/(x\-)?pkcs7-signature; name="smime\.p7s"
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename="smime\.p7s"
(?:^[a-zA-Z0-9\/\\r\\n+]*={0,2})
--$boundary--
OEL;
$this->assertValidVerify($expectedBody, $messageStream);
unset($messageStream);
}
public function testSignedMessageExtraCerts()
{
$message = (new Swift_Message('Wonderful Subject'))
->setFrom(['john@doe.com' => 'John Doe'])
->setTo(['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 testSignedMessageBinary()
{
$message = (new Swift_Message('Wonderful Subject'))
->setFrom(['john@doe.com' => 'John Doe'])
->setTo(['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 testSignedMessageWithAttachments()
{
$message = (new Swift_Message('Wonderful Subject'))
->setFrom(['john@doe.com' => 'John Doe'])
->setTo(['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 = (new Swift_Message('Wonderful Subject'))
->setFrom(['john@doe.com' => 'John Doe'])
->setTo(['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', ['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 testEncryptedMessageWithFullyWrappedMessage()
{
$message = (new Swift_Message('Middle-out compression secrets'))
->setFrom(['richard@piedpiper.com' => 'Richard Hendricks'])
->setTo(['jared@piedpiper.com' => 'Jared Dunn'])
->setBody('Here goes the entire algorithm...');
$originalMessage = $message->toString();
$signer = new Swift_Signers_SMimeSigner();
$signer->setEncryptCertificate($this->samplesDir.'smime/encrypt.crt');
$signer->setWrapFullMessage(true);
$message->attachSigner($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', ['file://'.$this->samplesDir.'smime/encrypt.key', 'swift'])) {
$this->fail(sprintf('Decrypt of the message failed. Internal error "%s".', openssl_error_string()));
}
$decryptedMessage = $decryptedMessageStream->getContent();
$decryptedHeaders = self::getHeadersOfMessage($decryptedMessage);
$this->assertEquals('message/rfc822; charset=utf-8', $decryptedHeaders['content-type']);
$this->assertEquals('7bit', $decryptedHeaders['content-transfer-encoding']);
$decryptedMessageBody = self::getBodyOfMessage($decryptedMessage);
$this->assertEquals($originalMessage, $decryptedMessageBody);
unset($decryptedMessageStream, $messageStream);
}
public function testEncryptedMessageWithMultipleCerts()
{
$message = (new Swift_Message('Wonderful Subject'))
->setFrom(['john@doe.com' => 'John Doe'])
->setTo(['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', $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', ['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', ['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 = (new Swift_Message('Wonderful Subject'))
->setFrom(['john@doe.com' => 'John Doe'])
->setTo(['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', ['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 = (new Swift_Message('Wonderful Subject'))
->setFrom(['john@doe.com' => 'John Doe'])
->setTo(['receiver@domain.org', 'other@domain.org' => 'A name'])
->setBody('Here is the message itself');
$originalMessage = $message->toString();
$signer = new Swift_Signers_SMimeSigner();
$signer->setSignCertificate($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>Content-Type: application/(x\-)?pkcs7-mime; smime-type=enveloped-data;
name="smime\.p7m"; charset=utf-8
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename="smime\.p7m"
(?:^[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', ['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);
$actual = self::getBodyOfMessage($actual);
if (!$this->assertRegExp('%^'.$expected.'$\s*%m', $actual)) {
return false;
}
$opensslOutput = new Swift_ByteStream_TemporaryFileByteStream();
$verify = openssl_pkcs7_verify($messageStream->getPath(), null, $opensslOutput->getPath(), [$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 trim(substr($message, strpos($message, "\r\n\r\n")));
}
/**
* Strips of the sender headers and Mime-Version.
*/
protected function cleanMessage($content)
{
$newContent = '';
$headers = self::getHeadersOfMessage($content);
foreach ($headers as $headerName => $value) {
if (!in_array($headerName, ['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 $newContent."\r\n".self::getBodyOfMessage($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");
$headerData = trim(substr($message, 0, $headersPosEnd));
$headerLines = explode("\r\n", $headerData);
$headers = [];
if (false === $headerLines) {
return $headers;
}
// Transform header lines into an associative array
$currentHeaderName = '';
foreach ($headerLines as $headerLine) {
// Handle headers that span multiple lines
if (false === strpos($headerLine, ':')) {
$headers[$currentHeaderName] .= ' '.trim($headerLine);
continue;
}
$header = explode(':', $headerLine, 2);
$currentHeaderName = strtolower($header[0]);
$headers[$currentHeaderName] = trim($header[1]);
}
return $headers;
}
}