diff --git a/lib/Cake/Log/Engine/FileLog.php b/lib/Cake/Log/Engine/FileLog.php
index 071f12f8d..22c1a9992 100644
--- a/lib/Cake/Log/Engine/FileLog.php
+++ b/lib/Cake/Log/Engine/FileLog.php
@@ -206,7 +206,7 @@ class FileLog extends BaseLog {
 
 		if ($this->_config['rotate']) {
 			$files = glob($filepath . '.*');
-			if (count($files) === $this->_config['rotate']) {
+			while (count($files) >= $this->_config['rotate']) {
 				unlink(array_shift($files));
 			}
 		}
diff --git a/lib/Cake/Test/Case/Log/Engine/FileLogTest.php b/lib/Cake/Test/Case/Log/Engine/FileLogTest.php
index 825adb9f0..4eba6cfad 100644
--- a/lib/Cake/Test/Case/Log/Engine/FileLogTest.php
+++ b/lib/Cake/Test/Case/Log/Engine/FileLogTest.php
@@ -117,6 +117,8 @@ class FileLogTest extends CakeTestCase {
 		$result = file_get_contents($files[1]);
 		$this->assertRegExp('/Warning: Test warning second/', $result);
 
+		file_put_contents($path . 'error.log.0000000000', "The oldest log file with over 35 bytes.\n");
+
 		sleep(1);
 		clearstatcache();
 		$log->write('warning', 'Test warning fourth');