diff --git a/src/sagemaker/local/utils.py b/src/sagemaker/local/utils.py
index a9729ddebb..e7d701ae8e 100644
--- a/src/sagemaker/local/utils.py
+++ b/src/sagemaker/local/utils.py
@@ -62,7 +62,7 @@ def move_to_destination(source, destination, job_name, sagemaker_session):
         final_uri = destination
     elif parsed_uri.scheme == "s3":
         bucket = parsed_uri.netloc
-        path = "%s%s" % (parsed_uri.path.lstrip("/"), job_name)
+        path = _create_s3_prefix(parsed_uri.path, job_name)
         final_uri = "s3://%s/%s" % (bucket, path)
         sagemaker_session.upload_data(source, bucket, path)
     else:
@@ -72,6 +72,22 @@ def move_to_destination(source, destination, job_name, sagemaker_session):
     return final_uri
 
 
+def _create_s3_prefix(path, job_name):
+    """Constructs a path out of the given path and job name to be
+    used as an S3 prefix.
+
+    Args:
+        path (str): the original path. If the path is only ``"/"``,
+            then it is ignored.
+        job_name (str): the job name to be appended to the path.
+
+    Returns:
+        str: an S3 prefix of the form ``"path/job_name"``
+    """
+    path = path.strip("/")
+    return job_name if path == "" else "/".join((path, job_name))
+
+
 def recursive_copy(source, destination):
     """A wrapper around distutils.dir_util.copy_tree but won't throw any
     exception when the source directory does not exist.
diff --git a/tests/integ/test_chainer_train.py b/tests/integ/test_chainer_train.py
index 56673de77b..add2efce1a 100644
--- a/tests/integ/test_chainer_train.py
+++ b/tests/integ/test_chainer_train.py
@@ -137,6 +137,8 @@ def _run_mnist_training_job(
         train_instance_type=instance_type,
         sagemaker_session=sagemaker_session,
         hyperparameters={"epochs": 1},
+        # test output_path without trailing slash
+        output_path="s3://{}".format(sagemaker_session.default_bucket()),
     )
 
     train_input = "file://" + os.path.join(data_path, "train")
diff --git a/tests/unit/test_local_utils.py b/tests/unit/test_local_utils.py
index 349a920237..6b2a0b0266 100644
--- a/tests/unit/test_local_utils.py
+++ b/tests/unit/test_local_utils.py
@@ -20,15 +20,33 @@
 
 @patch("shutil.rmtree", Mock())
 @patch("sagemaker.local.utils.recursive_copy")
-def test_move_to_destination(recursive_copy):
+def test_move_to_destination_local(recursive_copy):
     # local files will just be recursively copied
     sagemaker.local.utils.move_to_destination("/tmp/data", "file:///target/dir/", "job", None)
     recursive_copy.assert_called_with("/tmp/data", "/target/dir/")
 
-    # s3 destination will upload to S3
+
+@patch("shutil.rmtree", Mock())
+@patch("sagemaker.local.utils.recursive_copy")
+def test_move_to_destination_s3(recursive_copy):
     sms = Mock()
+
+    # without trailing slash in prefix
     sagemaker.local.utils.move_to_destination("/tmp/data", "s3://bucket/path", "job", sms)
-    sms.upload_data.assert_called()
+    sms.upload_data.assert_called_with("/tmp/data", "bucket", "path/job")
+    recursive_copy.assert_not_called()
+
+    # with trailing slash in prefix
+    sagemaker.local.utils.move_to_destination("/tmp/data", "s3://bucket/path/", "job", sms)
+    sms.upload_data.assert_called_with("/tmp/data", "bucket", "path/job")
+
+    # without path, with trailing slash
+    sagemaker.local.utils.move_to_destination("/tmp/data", "s3://bucket/", "job", sms)
+    sms.upload_data.assert_called_with("/tmp/data", "bucket", "job")
+
+    # without path, without trailing slash
+    sagemaker.local.utils.move_to_destination("/tmp/data", "s3://bucket", "job", sms)
+    sms.upload_data.assert_called_with("/tmp/data", "bucket", "job")
 
 
 def test_move_to_destination_illegal_destination():