From 4a92e525c57a743510b035ebf3a0bad067542c2a Mon Sep 17 00:00:00 2001
From: =?utf8?q?Tim=20D=C3=BCsterhus?= <duesterhus@woltlab.com>
Date: Mon, 14 Apr 2014 18:00:32 +0200
Subject: [PATCH] Add STARTTLS support to SMTPMailSender

---
 .../files/lib/system/io/RemoteFile.class.php  | 22 +++++++++++++
 .../lib/system/mail/SMTPMailSender.class.php  | 32 +++++++++++++++++--
 2 files changed, 52 insertions(+), 2 deletions(-)

diff --git a/wcfsetup/install/files/lib/system/io/RemoteFile.class.php b/wcfsetup/install/files/lib/system/io/RemoteFile.class.php
index 415cc8d325..4ff441d42c 100644
--- a/wcfsetup/install/files/lib/system/io/RemoteFile.class.php
+++ b/wcfsetup/install/files/lib/system/io/RemoteFile.class.php
@@ -72,4 +72,26 @@ class RemoteFile extends File {
 	public function getErrorDesc() {
 		return $this->errorDesc;
 	}
+	
+	/**
+	 * Switches TLS support for this connection.
+	 * Usually used in combination with 'STARTTLS'
+	 * 
+	 * @param	boolean	$enable		Whether TLS support should be enabled
+	 * @return	boolean			True on success, false otherwise
+	 */
+	public function setTLS($enable) {
+		if (!$this->hasTLSSupport()) return false;
+		
+		return stream_socket_enable_crypto($this->resource, $enable, STREAM_CRYPTO_METHOD_TLS_CLIENT);
+	}
+	
+	/**
+	 * Returns whether TLS support is available.
+	 * 
+	 * @return	boolean
+	 */
+	public function hasTLSSupport() {
+		return function_exists('stream_socket_enable_crypto');
+	}
 }
diff --git a/wcfsetup/install/files/lib/system/mail/SMTPMailSender.class.php b/wcfsetup/install/files/lib/system/mail/SMTPMailSender.class.php
index 772903b191..52b7ed03a9 100644
--- a/wcfsetup/install/files/lib/system/mail/SMTPMailSender.class.php
+++ b/wcfsetup/install/files/lib/system/mail/SMTPMailSender.class.php
@@ -7,7 +7,7 @@ use wcf\util\StringUtil;
 /**
  * Sends a Mail with a connection to a smtp server.
  * 
- * @author	Alexander Ebert
+ * @author	Tim Duesterhus, Alexander Ebert
  * @copyright	2001-2014 WoltLab GmbH
  * @license	GNU Lesser General Public License <http://opensource.org/licenses/lgpl-license.php>
  * @package	com.woltlab.wcf
@@ -74,8 +74,35 @@ class SMTPMailSender extends MailSender {
 		
 		// send ehlo
 		$this->write('EHLO '.$host);
-		$this->getSMTPStatus();
+		$extensions = explode(Mail::$lineEnding, $this->read());
+		$this->getSMTPStatus(array_shift($extensions));
 		if ($this->statusCode == 250) {
+			$extensions = array_map(function($element) {
+				return strtolower(substr($element, 4));
+			}, $extensions);
+			
+			if ($this->connection->hasTLSSupport() && in_array('starttls', $extensions)) {
+				$this->write('STARTTLS');
+				$this->getSMTPStatus();
+				
+				if ($this->statusCode != 220) {
+					throw new SystemException($this->formatError("cannot enable STARTTLS, though '".MAIL_SMTP_HOST.":".MAIL_SMTP_PORT."' advertised it"));
+				}
+				
+				if (!$this->connection->setTLS(true)) {
+					throw new SystemException('enabling TLS failed');
+				}
+				
+				// repeat EHLO
+				$this->write('EHLO '.$host);
+				$extensions = explode(Mail::$lineEnding, $this->read());
+				$this->getSMTPStatus(array_shift($extensions));
+				
+				if ($this->statusCode != 250) {
+					throw new SystemException($this->formatError("could not EHLO after enabling STARTTLS at '".MAIL_SMTP_HOST.":".MAIL_SMTP_PORT."'"));
+				}
+			}
+			
 			// do authentication
 			if (MAIL_SMTP_USER != '' || MAIL_SMTP_PASSWORD != '') {
 				$this->auth();
@@ -237,6 +264,7 @@ class SMTPMailSender extends MailSender {
 			$result .= $read;
 			if (substr($read, 3, 1) == " ") break;
 		}
+		
 		return $result;
 	}
 	
-- 
2.20.1