diff --git a/lib/Cake/Network/CakeRequest.php b/lib/Cake/Network/CakeRequest.php
index 59b2ee2a9..e5574c0e0 100644
--- a/lib/Cake/Network/CakeRequest.php
+++ b/lib/Cake/Network/CakeRequest.php
@@ -305,7 +305,7 @@ class CakeRequest implements ArrayAccess {
 		$this->webroot = $base . '/';
 
 		$docRoot = env('DOCUMENT_ROOT');
-		$docRootContainsWebroot = strpos($docRoot, $dir . '/' . $webroot);
+		$docRootContainsWebroot = strpos($docRoot, $dir . DS . $webroot);
 
 		if (!empty($base) || !$docRootContainsWebroot) {
 			if (strpos($this->webroot, '/' . $dir . '/') === false) {