diff --git a/server/src/main/java/com/metamx/druid/loading/SingleSegmentLoader.java b/server/src/main/java/com/metamx/druid/loading/SingleSegmentLoader.java
index 6ff5eda85cc..ed9f206f665 100644
--- a/server/src/main/java/com/metamx/druid/loading/SingleSegmentLoader.java
+++ b/server/src/main/java/com/metamx/druid/loading/SingleSegmentLoader.java
@@ -82,8 +82,15 @@ public class SingleSegmentLoader implements SegmentLoader
             throw new SegmentLoadingException(e, "Error deleting localDir[%s]", localStorageDir);
           }
         }
+        final File parentDir = localStorageDir.getParentFile();
+        if (!parentDir.exists()) {
+          log.info("Parent[%s] didn't exist, creating.");
+          parentDir.mkdirs();
+        }
 
-        legacyStorageDir.renameTo(localStorageDir);
+        if (!legacyStorageDir.renameTo(localStorageDir)) {
+          log.info("Failed moving [%s] to [%s]", legacyStorageDir, localStorageDir);
+        }
       }
     }