diff --git a/phpBB/includes/message_parser.php b/phpBB/includes/message_parser.php
index 6e626eeee8..72c101f7a3 100644
--- a/phpBB/includes/message_parser.php
+++ b/phpBB/includes/message_parser.php
@@ -1317,7 +1317,7 @@ class parse_message extends bbcode_firstpass
 				}
 
 				// (assertion)
-				$match[] = '(?<=^|[\n .])' . preg_quote($row['code'], '#') . '(?![^<>]*>)';
+				$match[] = preg_quote($row['code'], '#');
 				$replace[] = '<!-- s' . $row['code'] . ' --><img src="{SMILIES_PATH}/' . $row['smiley_url'] . '" alt="' . $row['code'] . '" title="' . $row['emotion'] . '" /><!-- s' . $row['code'] . ' -->';
 			}
 			$db->sql_freeresult($result);
@@ -1327,7 +1327,7 @@ class parse_message extends bbcode_firstpass
 		{
 			if ($max_smilies)
 			{
-				$num_matches = preg_match_all('#' . implode('|', $match) . '#', $this->message, $matches);
+				$num_matches = preg_match_all('#(?<=^|[\n .])(?:' . implode('|', $match) . ')(?![^<>]*>)#', $this->message, $matches);
 				unset($matches);
 
 				if ($num_matches !== false && $num_matches > $max_smilies)
@@ -1338,7 +1338,7 @@ class parse_message extends bbcode_firstpass
 			}
 
 			// Make sure the delimiter # is added in front and at the end of every element within $match
-			$this->message = trim(preg_replace(explode(chr(0), '#' . implode('#' . chr(0) . '#', $match) . '#'), $replace, $this->message));
+			$this->message = trim(preg_replace(explode(chr(0), '#(?<=^|[\n .])' . implode('(?![^<>]*>)#' . chr(0) . '#(?<=^|[\n .])', $match) . '(?![^<>]*>)#'), $replace, $this->message));
 		}
 	}