diff --git a/ironic_python_agent/extensions/standby.py b/ironic_python_agent/extensions/standby.py
index 1add183df..3a496ab11 100644
--- a/ironic_python_agent/extensions/standby.py
+++ b/ironic_python_agent/extensions/standby.py
@@ -74,6 +74,19 @@ def _download_with_proxy(image_info, url, image_id):
     resp = None
     for attempt in range(CONF.image_download_connection_retries + 1):
         try:
+            # NOTE(TheJulia) The get request below does the following:
+            # * Performs dns lookups, if necessary
+            # * Opens the TCP socket to the remote host
+            # * Negotiates TLS, if applicable
+            # * Checks cert validity, if necessary, which may be
+            #   more tcp socket connections.
+            # * Issues the get request and then returns back to the caller the
+            #   handler which is used to stream the data into the agent.
+            # While this all may be at risk of transitory interrupts, most of
+            # these socket will have timeouts applied to them, although not
+            # exactly just as the timeout value exists. The risk in transitory
+            # failure is more so once we've started the download and we are
+            # processing the incoming data.
             resp = requests.get(url, stream=True, proxies=proxies,
                                 verify=verify, cert=cert,
                                 timeout=CONF.image_download_connection_timeout)
@@ -275,6 +288,7 @@ class ImageDownload(object):
                  any reason.
         """
         self._time = time_obj or time.time()
+        self._last_chunk_time = None
         self._image_info = image_info
         self._request = None
 
@@ -337,8 +351,25 @@ class ImageDownload(object):
                   which is a constant in this module.
         """
         for chunk in self._request.iter_content(IMAGE_CHUNK_SIZE):
-            self._hash_algo.update(chunk)
-            yield chunk
+            # Per requests forum posts/discussions, iter_content should
+            # periodically yield to the caller for the client to do things
+            # like stopwatch and potentially interrupt the download.
+            # While this seems weird and doesn't exactly seem to match the
+            # patterns in requests and urllib3, it does appear to be the
+            # case. Field testing in environments where TCP sockets were
+            # discovered in a read hanged state were navigated with
+            # this code.
+            if chunk:
+                self._last_chunk_time = time.time()
+                self._hash_algo.update(chunk)
+                yield chunk
+            elif (time.time() - self._last_chunk_time
+                  > CONF.image_download_connection_timeout):
+                LOG.error('Timeout reached waiting for a chunk of data from '
+                          'a remote server.')
+                raise errors.ImageDownloadError(
+                    self._image_info['id'],
+                    'Timed out reading next chunk from webserver')
 
     def verify_image(self, image_location):
         """Verifies the checksum of the local images matches expectations.
diff --git a/ironic_python_agent/tests/unit/extensions/test_standby.py b/ironic_python_agent/tests/unit/extensions/test_standby.py
index e9bd9c130..adb2e0838 100644
--- a/ironic_python_agent/tests/unit/extensions/test_standby.py
+++ b/ironic_python_agent/tests/unit/extensions/test_standby.py
@@ -14,6 +14,7 @@
 
 import os
 import tempfile
+import time
 
 import mock
 from oslo_concurrency import processutils
@@ -1111,6 +1112,61 @@ class TestStandbyExtension(base.IronicAgentTest):
                         '/dev/fake root_uuid=ROOT')
         self.assertEqual(expected_msg, result_msg)
 
+    @mock.patch('ironic_lib.disk_utils.fix_gpt_partition', autospec=True)
+    @mock.patch('hashlib.md5', autospec=True)
+    @mock.patch('six.moves.builtins.open', autospec=True)
+    @mock.patch('requests.get', autospec=True)
+    def test_stream_raw_image_onto_device_socket_read_timeout(
+            self, requests_mock, open_mock, md5_mock, fix_gpt_mock):
+
+        class create_timeout(object):
+            status_code = 200
+
+            def __init__(self, url, stream, proxies, verify, cert, timeout):
+                time.sleep(1)
+                self.count = 0
+
+            def __iter__(self):
+                return self
+
+            def __next__(self):
+                if self.count:
+                    time.sleep(0.1)
+                    return None
+                if self.count < 3:
+                    self.count += 1
+                    return "meow"
+                else:
+                    time.sleep(30)
+                    raise StopIteration
+
+            # Python 2
+            next = __next__
+
+            def iter_content(self, chunk_size):
+                return self
+
+        self.config(image_download_connection_timeout=1)
+        image_info = _build_fake_image_info()
+        file_mock = mock.Mock()
+        open_mock.return_value.__enter__.return_value = file_mock
+        file_mock.read.return_value = None
+        hexdigest_mock = md5_mock.return_value.hexdigest
+        hexdigest_mock.return_value = image_info['checksum']
+        requests_mock.side_effect = create_timeout
+        self.assertRaisesRegex(
+            errors.ImageDownloadError,
+            'Timed out reading next chunk',
+            self.agent_extension._stream_raw_image_onto_device,
+            image_info,
+            '/dev/foo')
+        requests_mock.assert_called_once_with(image_info['urls'][0],
+                                              cert=None, verify=True,
+                                              stream=True, proxies={},
+                                              timeout=1)
+        file_mock.write.assert_called_once_with('meow')
+        self.assertFalse(fix_gpt_mock.called)
+
     def test__message_format_partition_bios(self):
         image_info = _build_fake_partition_image_info()
         msg = ('image ({}) already present on device {} ')
diff --git a/releasenotes/notes/timeout_on_file_download-ed77918318316075.yaml b/releasenotes/notes/timeout_on_file_download-ed77918318316075.yaml
new file mode 100644
index 000000000..c90073e3a
--- /dev/null
+++ b/releasenotes/notes/timeout_on_file_download-ed77918318316075.yaml
@@ -0,0 +1,9 @@
+---
+fixes:
+  - |
+    Fixes failure to detect a hung file download connection in the
+    event that the kernel has not rapidly detected that the remote
+    server has hung up the socket. This can happen when there is
+    intermittent and transient connectivity issues such as those
+    that can occur due to LACP failure response hold-downs timers
+    in switching fabrics.