diff --git a/ironic_python_agent/extensions/standby.py b/ironic_python_agent/extensions/standby.py
index dd7aaa889..909aded2c 100644
--- a/ironic_python_agent/extensions/standby.py
+++ b/ironic_python_agent/extensions/standby.py
@@ -408,16 +408,30 @@ def _download_image(image_info):
     """
     starttime = time.time()
     image_location = _image_location(image_info)
-    image_download = ImageDownload(image_info, time_obj=starttime)
-
-    with open(image_location, 'wb') as f:
+    for attempt in range(CONF.image_download_connection_retries + 1):
         try:
-            for chunk in image_download:
-                f.write(chunk)
-        except Exception as e:
-            msg = 'Unable to write image to {}. Error: {}'.format(
-                image_location, str(e))
-            raise errors.ImageDownloadError(image_info['id'], msg)
+            image_download = ImageDownload(image_info, time_obj=starttime)
+
+            with open(image_location, 'wb') as f:
+                try:
+                    for chunk in image_download:
+                        f.write(chunk)
+                except Exception as e:
+                    msg = 'Unable to write image to {}. Error: {}'.format(
+                        image_location, str(e))
+                    raise errors.ImageDownloadError(image_info['id'], msg)
+        except errors.ImageDownloadError as e:
+            if attempt == CONF.image_download_connection_retries:
+                raise
+            else:
+                LOG.warning('Image download failed, %(attempt)s of %(total)s: '
+                            '%(error)s',
+                            {'attempt': attempt,
+                             'total': CONF.image_download_connection_retries,
+                             'error': e})
+                time.sleep(CONF.image_download_connection_retry_interval)
+        else:
+            break
 
     totaltime = time.time() - starttime
     LOG.info("Image downloaded from {} in {} seconds".format(image_location,
@@ -553,16 +567,31 @@ class StandbyExtension(base.BaseAgentExtension):
              match the checksum as reported by glance in image_info.
         """
         starttime = time.time()
-        image_download = ImageDownload(image_info, time_obj=starttime)
-
-        with open(device, 'wb+') as f:
+        total_retries = CONF.image_download_connection_retries
+        for attempt in range(total_retries + 1):
             try:
-                for chunk in image_download:
-                    f.write(chunk)
-            except Exception as e:
-                msg = 'Unable to write image to device {}. Error: {}'.format(
-                      device, str(e))
-                raise errors.ImageDownloadError(image_info['id'], msg)
+                image_download = ImageDownload(image_info, time_obj=starttime)
+
+                with open(device, 'wb+') as f:
+                    try:
+                        for chunk in image_download:
+                            f.write(chunk)
+                    except Exception as e:
+                        msg = ('Unable to write image to device {}. '
+                               'Error: {}').format(device, str(e))
+                        raise errors.ImageDownloadError(image_info['id'], msg)
+            except errors.ImageDownloadError as e:
+                if attempt == CONF.image_download_connection_retries:
+                    raise
+                else:
+                    LOG.warning('Image download failed, %(attempt)s of '
+                                '%(total)s: %(error)s',
+                                {'attempt': attempt,
+                                 'total': total_retries,
+                                 'error': e})
+                    time.sleep(CONF.image_download_connection_retry_interval)
+            else:
+                break
 
         totaltime = time.time() - starttime
         LOG.info("Image streamed onto device {} in {} "
diff --git a/ironic_python_agent/tests/unit/extensions/test_standby.py b/ironic_python_agent/tests/unit/extensions/test_standby.py
index eaff2b272..fe212a9a2 100644
--- a/ironic_python_agent/tests/unit/extensions/test_standby.py
+++ b/ironic_python_agent/tests/unit/extensions/test_standby.py
@@ -1126,6 +1126,8 @@ class TestStandbyExtension(base.IronicAgentTest):
     @mock.patch('requests.get', autospec=True)
     def test_stream_raw_image_onto_device_write_error(self, requests_mock,
                                                       open_mock, md5_mock):
+        self.config(image_download_connection_timeout=1)
+        self.config(image_download_connection_retry_interval=0)
         image_info = _build_fake_image_info()
         response = requests_mock.return_value
         response.status_code = 200
@@ -1139,12 +1141,20 @@ class TestStandbyExtension(base.IronicAgentTest):
         self.assertRaises(errors.ImageDownloadError,
                           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=60)
-        # Assert write was only called once and failed!
-        file_mock.write.assert_called_once_with('some')
+        calls = [mock.call('http://example.org', cert=None, proxies={},
+                           stream=True, timeout=1, verify=True),
+                 mock.call().iter_content(mock.ANY),
+                 mock.call('http://example.org', cert=None, proxies={},
+                           stream=True, timeout=1, verify=True),
+                 mock.call().iter_content(mock.ANY),
+                 mock.call('http://example.org', cert=None, proxies={},
+                           stream=True, timeout=1, verify=True),
+                 mock.call().iter_content(mock.ANY)]
+        requests_mock.assert_has_calls(calls)
+        write_calls = [mock.call('some'),
+                       mock.call('some'),
+                       mock.call('some')]
+        file_mock.write.assert_has_calls(write_calls)
 
     @mock.patch('ironic_lib.disk_utils.get_disk_identifier',
                 lambda dev: 'ROOT')
@@ -1191,6 +1201,7 @@ class TestStandbyExtension(base.IronicAgentTest):
                 return self
 
         self.config(image_download_connection_timeout=1)
+        self.config(image_download_connection_retry_interval=0)
         image_info = _build_fake_image_info()
         file_mock = mock.Mock()
         open_mock.return_value.__enter__.return_value = file_mock
@@ -1203,11 +1214,19 @@ class TestStandbyExtension(base.IronicAgentTest):
             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')
+
+        calls = [mock.call(image_info['urls'][0], cert=None, verify=True,
+                           stream=True, proxies={}, timeout=1),
+                 mock.call(image_info['urls'][0], cert=None, verify=True,
+                           stream=True, proxies={}, timeout=1),
+                 mock.call(image_info['urls'][0], cert=None, verify=True,
+                           stream=True, proxies={}, timeout=1)]
+        requests_mock.assert_has_calls(calls)
+
+        write_calls = [mock.call('meow'),
+                       mock.call('meow'),
+                       mock.call('meow')]
+        file_mock.write.assert_has_calls(write_calls)
         fix_gpt_mock.assert_not_called()
 
     def test__message_format_partition_bios(self):
diff --git a/releasenotes/notes/agent-fully-retries-image-downloads-67409a493c6d08ae.yaml b/releasenotes/notes/agent-fully-retries-image-downloads-67409a493c6d08ae.yaml
new file mode 100644
index 000000000..660ec4c81
--- /dev/null
+++ b/releasenotes/notes/agent-fully-retries-image-downloads-67409a493c6d08ae.yaml
@@ -0,0 +1,6 @@
+---
+fixes:
+  - |
+    Fixes deployment failures when the image download is interrupted
+    mid-stream while the contents are being downloaded. Previously retries
+    were limited to only opening the initial connection.