diff --git a/phpBB/docs/CHANGELOG.html b/phpBB/docs/CHANGELOG.html
index 1c1821fc8b..453d4c1c6d 100644
--- a/phpBB/docs/CHANGELOG.html
+++ b/phpBB/docs/CHANGELOG.html
@@ -115,6 +115,7 @@
 		<li>[Change] Allow years in future be selected for date custom profile field (Bug#14519)</li>
 		<li>[Fix] Don't display &quot;Avatars Disabled&quot; message on edit groups in UCP (Bug #14636)</li>
 		<li>[Change] Require confirm for deleting inactive users. (Bug #14641)</li>
+		<li>[Fix] Match custom BBCodes in the same way during first and second pass - patch provided by IBBoard (Bug #14268)</li>
 	</ul>
 
 	<a name="v30rc4"></a><h3>1.ii. Changes since 3.0.RC4</h3>
diff --git a/phpBB/includes/acp/acp_bbcodes.php b/phpBB/includes/acp/acp_bbcodes.php
index 1b5de909c3..21370036ee 100644
--- a/phpBB/includes/acp/acp_bbcodes.php
+++ b/phpBB/includes/acp/acp_bbcodes.php
@@ -331,6 +331,17 @@ class acp_bbcodes
 			)
 		);
 
+		$sp_tokens = array(
+			'URL'	 => '(?i)((?:' . str_replace(array('!', '\#'), array('\!', '#'), get_preg_expression('url')) . ')|(?:' . str_replace(array('!', '\#'), array('\!', '#'), get_preg_expression('www_url')) . '))(?-i)',
+			'LOCAL_URL'	 => '(?i)(' . str_replace(array('!', '\#'), array('\!', '#'), get_preg_expression('relative_url')) . ')(?-i)',
+			'EMAIL' => '([a-zA-Z0-9]+[a-zA-Z0-9\-\._]*@(?:(?:[0-9]{1,3}\.){3,5}[0-9]{1,3}|[a-zA-Z0-9]+[a-zA-Z0-9\-\._]*\.[a-zA-Z]+))',
+			'TEXT' => '(.*?)',
+			'SIMPLETEXT' => '([a-zA-Z0-9-+.,_ ]+)',
+			'IDENTIFIER' => '([a-zA-Z0-9-_]+)',
+			'COLOR' => '([a-zA-Z]+|#[0-9abcdefABCDEF]+)',
+			'NUMBER' => '([0-9]+)',
+		);
+
 		$pad = 0;
 		$modifiers = 'i';
 
@@ -376,7 +387,7 @@ class acp_bbcodes
 				$fp_match = str_replace(preg_quote($token, '!'), $regex, $fp_match);
 				$fp_replace = str_replace($token, $replace, $fp_replace);
 
-				$sp_match = str_replace(preg_quote($token, '!'), '(.*?)', $sp_match);
+				$sp_match = str_replace(preg_quote($token, '!'), $sp_tokens[$token_type], $sp_match);
 				$sp_replace = str_replace($token, '${' . ($n + 1) . '}', $sp_replace);
 			}
 
diff --git a/phpBB/includes/bbcode.php b/phpBB/includes/bbcode.php
index 6610a5c441..ef73762582 100644
--- a/phpBB/includes/bbcode.php
+++ b/phpBB/includes/bbcode.php
@@ -80,6 +80,7 @@ class bbcode
 		$bitfield = new bitfield($this->bbcode_bitfield);
 		$bbcodes_set = $bitfield->get_all_set();
 
+		$undid_bbcode_specialchars = false;
 		foreach ($bbcodes_set as $bbcode_id)
 		{
 			if (!empty($this->bbcode_cache[$bbcode_id]))
@@ -100,6 +101,14 @@ class bbcode
 
 					if (sizeof($preg['search']))
 					{
+						// we need to turn the entities back into their original form to allow the
+						// search patterns to work properly
+						if (!$undid_bbcode_specialchars)
+						{
+							$message = str_replace(array('&#58;', '&#46;'), array(':', '.'), $message);
+							$undid_bbcode_specialchars = true;
+						}
+
 						$message = preg_replace($preg['search'], $preg['replace'], $message);
 						$preg = array('search' => array(), 'replace' => array());
 					}