diff --git a/lhc_web/lib/core/lhcore/class.phpmailer.php b/lhc_web/lib/core/lhcore/class.phpmailer.php
index 3edac2e07f..55e0a4f941 100644
--- a/lhc_web/lib/core/lhcore/class.phpmailer.php
+++ b/lhc_web/lib/core/lhcore/class.phpmailer.php
@@ -31,7 +31,7 @@ class PHPMailer
      * The PHPMailer Version number.
      * @var string
      */
-    public $Version = '5.2.19';
+    public $Version = '5.2.21';
 
     /**
      * Email priority.
@@ -1364,20 +1364,24 @@ public function postSend()
      */
     protected function sendmailSend($header, $body)
     {
-        // CVE-2016-10033, CVE-2016-10045: Don't pass -f if characters will be escaped by escapeshellcmd when popen is called due to safe mode.
-        if (!empty($this->Sender) || ini_get('safe_mode')) {
+        // CVE-2016-10033, CVE-2016-10045: Don't pass -f if characters will be escaped.
+        if (!empty($this->Sender) and self::isShellSafe($this->Sender)) {
             if ($this->Mailer == 'qmail') {
-                $sendmail = sprintf('%s -f%s', escapeshellcmd($this->Sendmail), escapeshellarg($this->Sender));
+                $sendmailFmt = '%s -f%s';
             } else {
-                $sendmail = sprintf('%s -oi -f%s -t', escapeshellcmd($this->Sendmail), escapeshellarg($this->Sender));
+                $sendmailFmt = '%s -oi -f%s -t';
             }
         } else {
             if ($this->Mailer == 'qmail') {
-                $sendmail = sprintf('%s', escapeshellcmd($this->Sendmail));
+                $sendmailFmt = '%s';
             } else {
-                $sendmail = sprintf('%s -oi -t', escapeshellcmd($this->Sendmail));
+                $sendmailFmt = '%s -oi -t';
             }
         }
+
+        // TODO: If possible, this should be changed to escapeshellarg.  Needs thorough testing.
+        $sendmail = sprintf($sendmailFmt, escapeshellcmd($this->Sendmail), $this->Sender);
+
         if ($this->SingleTo) {
             foreach ($this->SingleToArray as $toAddr) {
                 if (!@$mail = popen($sendmail, 'w')) {
@@ -1423,6 +1427,40 @@ protected function sendmailSend($header, $body)
         return true;
     }
 
+    /**
+     * Fix CVE-2016-10033 and CVE-2016-10045 by disallowing potentially unsafe shell characters.
+     *
+     * Note that escapeshellarg and escapeshellcmd are inadequate for our purposes, especially on Windows.
+     * @param string $string The string to be validated
+     * @see https://github.com/PHPMailer/PHPMailer/issues/924 CVE-2016-10045 bug report
+     * @access protected
+     * @return boolean
+     */
+    protected static function isShellSafe($string)
+    {
+        // Future-proof
+        if (escapeshellcmd($string) !== $string
+            or !in_array(escapeshellarg($string), array("'$string'", "\"$string\""))
+        ) {
+            return false;
+        }
+
+        $length = strlen($string);
+
+        for ($i = 0; $i < $length; $i++) {
+            $c = $string[$i];
+
+            // All other characters have a special meaning in at least one common shell, including = and +.
+            // Full stop (.) has a special meaning in cmd.exe, but its impact should be negligible here.
+            // Note that this does permit non-Latin alphanumeric characters based on the current locale.
+            if (!ctype_alnum($c) && strpos('@_-.', $c) === false) {
+                return false;
+            }
+        }
+
+        return true;
+    }
+
     /**
      * Send mail using the PHP mail() function.
      * @param string $header The message headers
@@ -1444,8 +1482,8 @@ protected function mailSend($header, $body)
         //This sets the SMTP envelope sender which gets turned into a return-path header by the receiver
         if (!empty($this->Sender) and $this->validateAddress($this->Sender)) {
             // CVE-2016-10033, CVE-2016-10045: Don't pass -f if characters will be escaped.
-            if (escapeshellcmd($this->Sender) === $this->Sender && in_array(escapeshellarg($this->Sender), array("'$this->Sender'", "\"$this->Sender\""))) {
-                $params = sprintf('-f%s', escapeshellarg($this->Sender));
+            if (self::isShellSafe($this->Sender)) {
+                $params = sprintf('-f%s', $this->Sender);
             }
         }
         if (!empty($this->Sender) and !ini_get('safe_mode') and $this->validateAddress($this->Sender)) {
diff --git a/lhc_web/lib/core/lhcore/class.smtp.php b/lhc_web/lib/core/lhcore/class.smtp.php
index 6751879e73..4561389434 100644
--- a/lhc_web/lib/core/lhcore/class.smtp.php
+++ b/lhc_web/lib/core/lhcore/class.smtp.php
@@ -30,7 +30,7 @@ class SMTP
      * The PHPMailer SMTP version number.
      * @var string
      */
-    const VERSION = '5.2.19';
+    const VERSION = '5.2.21';
 
     /**
      * SMTP line break constant.
@@ -81,7 +81,7 @@ class SMTP
      * @deprecated Use the `VERSION` constant instead
      * @see SMTP::VERSION
      */
-    public $Version = '5.2.19';
+    public $Version = '5.2.21';
 
     /**
      * SMTP server port number.