diff --git a/gcloud/storage/blob.py b/gcloud/storage/blob.py
index fe73a9b1a9a0..92c11e412320 100644
--- a/gcloud/storage/blob.py
+++ b/gcloud/storage/blob.py
@@ -21,12 +21,14 @@
 import os
 import time
 
+import httplib2
 import six
 from six.moves.urllib.parse import quote
 
 from gcloud._helpers import _rfc3339_to_datetime
 from gcloud.credentials import generate_signed_url
 from gcloud.exceptions import NotFound
+from gcloud.exceptions import make_exception
 from gcloud.storage._helpers import _PropertyMixin
 from gcloud.storage._helpers import _scalar_property
 from gcloud.storage.acl import ObjectACL
@@ -346,6 +348,16 @@ def download_as_string(self, client=None):
         self.download_to_file(string_buffer, client=client)
         return string_buffer.getvalue()
 
+    @staticmethod
+    def _check_response_error(request, http_response):
+        """Helper for :meth:`upload_from_file`."""
+        info = http_response.info
+        status = int(info['status'])
+        if not 200 <= status < 300:
+            faux_response = httplib2.Response({'status': status})
+            raise make_exception(faux_response, http_response.content,
+                                 error_info=request.url)
+
     def upload_from_file(self, file_obj, rewind=False, size=None,
                          content_type=None, num_retries=6, client=None):
         """Upload the contents of this blob from a file-like object.
@@ -390,7 +402,8 @@ def upload_from_file(self, file_obj, rewind=False, size=None,
                        to the ``client`` stored on the blob's bucket.
 
         :raises: :class:`ValueError` if size is not passed in and can not be
-                 determined
+                 determined; :class:`gcloud.exceptions.GCloudError` if the
+                 upload response returns an error status.
         """
         client = self._require_client(client)
         # Use the private ``_connection`` rather than the public
@@ -452,7 +465,10 @@ def upload_from_file(self, file_obj, rewind=False, size=None,
         else:
             http_response = make_api_request(connection.http, request,
                                              retries=num_retries)
+
+        self._check_response_error(request, http_response)
         response_content = http_response.content
+
         if not isinstance(response_content,
                           six.string_types):  # pragma: NO COVER  Python3
             response_content = response_content.decode('utf-8')
diff --git a/gcloud/storage/test_blob.py b/gcloud/storage/test_blob.py
index 2d7778357a22..a116114843ed 100644
--- a/gcloud/storage/test_blob.py
+++ b/gcloud/storage/test_blob.py
@@ -418,7 +418,8 @@ def test_upload_from_file_size_failure(self):
     def _upload_from_file_simple_test_helper(self, properties=None,
                                              content_type_arg=None,
                                              expected_content_type=None,
-                                             chunk_size=5):
+                                             chunk_size=5,
+                                             status=None):
         from six.moves.http_client import OK
         from six.moves.urllib.parse import parse_qsl
         from six.moves.urllib.parse import urlsplit
@@ -426,7 +427,9 @@ def _upload_from_file_simple_test_helper(self, properties=None,
 
         BLOB_NAME = 'blob-name'
         DATA = b'ABCDEF'
-        response = {'status': OK}
+        if status is None:
+            status = OK
+        response = {'status': status}
         connection = _Connection(
             (response, b'{}'),
         )
@@ -463,6 +466,12 @@ def test_upload_from_file_simple(self):
         self._upload_from_file_simple_test_helper(
             expected_content_type='application/octet-stream')
 
+    def test_upload_from_file_simple_not_found(self):
+        from six.moves.http_client import NOT_FOUND
+        from gcloud.exceptions import NotFound
+        with self.assertRaises(NotFound):
+            self._upload_from_file_simple_test_helper(status=NOT_FOUND)
+
     def test_upload_from_file_simple_w_chunk_size_None(self):
         self._upload_from_file_simple_test_helper(
             expected_content_type='application/octet-stream',
@@ -572,6 +581,60 @@ def test_upload_from_file_resumable(self):
             'redirections': 5,
         })
 
+    def test_upload_from_file_resumable_w_error(self):
+        from six.moves.http_client import NOT_FOUND
+        from six.moves.urllib.parse import parse_qsl
+        from six.moves.urllib.parse import urlsplit
+        from gcloud._testing import _Monkey
+        from gcloud._testing import _NamedTemporaryFile
+        from gcloud.streaming import transfer
+        from gcloud.streaming.exceptions import HttpError
+
+        BLOB_NAME = 'blob-name'
+        DATA = b'ABCDEF'
+        loc_response = {'status': NOT_FOUND}
+        connection = _Connection(
+            (loc_response, b'{"error": "no such bucket"}'),
+        )
+        client = _Client(connection)
+        bucket = _Bucket(client)
+        blob = self._makeOne(BLOB_NAME, bucket=bucket)
+        blob._CHUNK_SIZE_MULTIPLE = 1
+        blob.chunk_size = 5
+
+        # Set the threshhold low enough that we force a resumable uploada.
+        with _Monkey(transfer, RESUMABLE_UPLOAD_THRESHOLD=5):
+            with _NamedTemporaryFile() as temp:
+                with open(temp.name, 'wb') as file_obj:
+                    file_obj.write(DATA)
+                with open(temp.name, 'rb') as file_obj:
+                    with self.assertRaises(HttpError):
+                        blob.upload_from_file(file_obj, rewind=True)
+
+        rq = connection.http._requested
+        self.assertEqual(len(rq), 1)
+
+        # Requested[0]
+        headers = dict(
+            [(x.title(), str(y)) for x, y in rq[0].pop('headers').items()])
+        self.assertEqual(headers['X-Upload-Content-Length'], '6')
+        self.assertEqual(headers['X-Upload-Content-Type'],
+                         'application/octet-stream')
+
+        uri = rq[0].pop('uri')
+        scheme, netloc, path, qs, _ = urlsplit(uri)
+        self.assertEqual(scheme, 'http')
+        self.assertEqual(netloc, 'example.com')
+        self.assertEqual(path, '/b/name/o')
+        self.assertEqual(dict(parse_qsl(qs)),
+                         {'uploadType': 'resumable', 'name': BLOB_NAME})
+        self.assertEqual(rq[0], {
+            'method': 'POST',
+            'body': '',
+            'connection_type': None,
+            'redirections': 5,
+        })
+
     def test_upload_from_file_w_slash_in_name(self):
         from six.moves.http_client import OK
         from six.moves.urllib.parse import parse_qsl