diff --git a/lib/Cake/Network/CakeRequest.php b/lib/Cake/Network/CakeRequest.php
index 75689fa87..c2c498d7b 100644
--- a/lib/Cake/Network/CakeRequest.php
+++ b/lib/Cake/Network/CakeRequest.php
@@ -278,10 +278,10 @@ class CakeRequest implements ArrayAccess {
 		$docRootContainsWebroot = strpos($docRoot, $dir . '/' . $webroot);
 
 		if (!empty($base) || !$docRootContainsWebroot) {
-			if (strpos($this->webroot, $dir) === false) {
+			if (strpos($this->webroot, '/' . $dir . '/') === false) {
 				$this->webroot .= $dir . '/' ;
 			}
-			if (strpos($this->webroot, $webroot) === false) {
+			if (strpos($this->webroot, '/' . $webroot . '/') === false) {
 				$this->webroot .= $webroot . '/';
 			}
 		}
diff --git a/lib/Cake/Test/Case/Network/CakeRequestTest.php b/lib/Cake/Test/Case/Network/CakeRequestTest.php
index 95bf2177f..1ccd441b2 100644
--- a/lib/Cake/Test/Case/Network/CakeRequestTest.php
+++ b/lib/Cake/Test/Case/Network/CakeRequestTest.php
@@ -1041,6 +1041,29 @@ class CakeRequestTest extends CakeTestCase {
 		$this->assertEquals('/app/webroot/', $request->webroot);
 	}
 
+/**
+ * Check that a sub-directory containing app|webroot doesn't get mishandled when re-writing is off.
+ *
+ * @return void
+ */
+	public function testBaseUrlWithAppAndWebrootInDirname() {
+		Configure::write('App.baseUrl', '/approval/index.php');
+		$_SERVER['DOCUMENT_ROOT'] = '/Users/markstory/Sites/';
+		$_SERVER['SCRIPT_FILENAME'] = '/Users/markstory/Sites/approval/index.php';
+
+		$request = new CakeRequest();
+		$this->assertEquals('/approval/index.php', $request->base);
+		$this->assertEquals('/approval/app/webroot/', $request->webroot);
+
+		Configure::write('App.baseUrl', '/webrootable/index.php');
+		$_SERVER['DOCUMENT_ROOT'] = '/Users/markstory/Sites/';
+		$_SERVER['SCRIPT_FILENAME'] = '/Users/markstory/Sites/webrootable/index.php';
+
+		$request = new CakeRequest();
+		$this->assertEquals('/webrootable/index.php', $request->base);
+		$this->assertEquals('/webrootable/app/webroot/', $request->webroot);
+	}
+
 /**
  * test baseUrl with no rewrite, and using the app/webroot/index.php file as is normal with virtual hosts.
  *