diff --git a/ibm-cos-java-sdk-s3/src/main/java/com/ibm/cloud/objectstorage/services/s3/transfer/TransferManager.java b/ibm-cos-java-sdk-s3/src/main/java/com/ibm/cloud/objectstorage/services/s3/transfer/TransferManager.java
index a860286431..7523777ab5 100644
--- a/ibm-cos-java-sdk-s3/src/main/java/com/ibm/cloud/objectstorage/services/s3/transfer/TransferManager.java
+++ b/ibm-cos-java-sdk-s3/src/main/java/com/ibm/cloud/objectstorage/services/s3/transfer/TransferManager.java
@@ -1512,7 +1512,7 @@ public MultipleFileDownload downloadDirectory(String bucketName, String keyPrefi
 
     private boolean leavesRoot(File localBaseDirectory, String key) {
         try {
-            return !new File(localBaseDirectory, key).getCanonicalPath().startsWith(localBaseDirectory.getCanonicalPath());
+            return !new File(localBaseDirectory, key).getCanonicalFile().toPath().startsWith(localBaseDirectory.getCanonicalFile().toPath());
         } catch (IOException e) {
             throw new RuntimeException("Unable to canonicalize paths",  e);
         }