diff --git a/ironic_python_agent/ironic_api_client.py b/ironic_python_agent/ironic_api_client.py
index fda420d99..67f9e6b91 100644
--- a/ironic_python_agent/ironic_api_client.py
+++ b/ironic_python_agent/ironic_api_client.py
@@ -167,12 +167,41 @@ class APIClient(object):
                 'GET', self.lookup_api,
                 headers=self._get_ironic_api_version_header(),
                 params=params)
-        except Exception as err:
-            LOG.exception(
-                'Unhandled error looking up node with addresses %r at %s: %s',
-                params['addresses'], self.api_url, err,
+        except (requests.exceptions.Timeout,
+                requests.exceptions.ConnectTimeout,
+                requests.exceptions.ConnectionError,
+                requests.exceptions.ReadTimeout,
+                requests.exceptions.HTTPError) as err:
+            LOG.warning(
+                'Error detected while attempting to perform lookup '
+                'with %s, retrying. Error: %s', self.api_url, err
             )
             return False
+        except Exception as err:
+            # NOTE(TheJulia): If you're looking here, and you're wondering
+            # why the retry logic is not working or your investigating a weird
+            # error or even IPA just exiting,
+            # See https://storyboard.openstack.org/#!/story/2007968
+            # To be clear, we're going to try to provide as much detail as
+            # possible in the exit handling
+            msg = ('Unhandled error looking up node with addresses {} at '
+                   '{}: {}'.format(params['addresses'], self.api_url, err))
+            # No matter what we do at this point, IPA is going to exit.
+            # This is because we don't know why the exception occured and
+            # we likely should not try to retry as such.
+            # We will attempt to provide as much detail to the logs as
+            # possible as to what occured, although depending on the logging
+            # subsystem, additional errors can occur, thus the additional
+            # handling below.
+            try:
+                LOG.exception(msg)
+                return False
+            except Exception as exc_err:
+                LOG.error(msg)
+                exc_msg = ('Unexpected exception occured while trying to '
+                           'log additional detail. Error: {}'.format(exc_err))
+                LOG.error(exc_msg)
+                raise errors.LookupNodeError(msg)
 
         if response.status_code != requests.codes.OK:
             LOG.warning(
diff --git a/ironic_python_agent/tests/unit/test_ironic_api_client.py b/ironic_python_agent/tests/unit/test_ironic_api_client.py
index c0f8bb740..63e100fff 100644
--- a/ironic_python_agent/tests/unit/test_ironic_api_client.py
+++ b/ironic_python_agent/tests/unit/test_ironic_api_client.py
@@ -16,6 +16,7 @@ from unittest import mock
 
 from oslo_serialization import jsonutils
 from oslo_service import loopingcall
+import requests
 
 from ironic_python_agent import errors
 from ironic_python_agent import hardware
@@ -312,6 +313,47 @@ class TestBaseIronicPythonAgent(base.IronicAgentTest):
                           'node_uuid': 'someuuid'},
                          params)
 
+    @mock.patch.object(ironic_api_client, 'LOG', autospec=True)
+    def test_do_lookup_transient_exceptions(self, mock_log):
+        exc_list = [requests.exceptions.ConnectionError,
+                    requests.exceptions.ReadTimeout,
+                    requests.exceptions.HTTPError,
+                    requests.exceptions.Timeout,
+                    requests.exceptions.ConnectTimeout]
+        self.api_client.session.request = mock.Mock()
+        for exc in exc_list:
+            self.api_client.session.request.reset_mock()
+            mock_log.reset_mock()
+            self.api_client.session.request.side_effect = exc
+            error = self.api_client._do_lookup(self.hardware_info,
+                                               node_uuid=None)
+            self.assertFalse(error)
+            mock_log.error.assert_has_calls([])
+            self.assertEqual(1, mock_log.warning.call_count)
+
+    @mock.patch.object(ironic_api_client, 'LOG', autospec=True)
+    def test_do_lookup_unknown_exception(self, mock_log):
+        self.api_client.session.request = mock.Mock()
+        self.api_client.session.request.side_effect = \
+            requests.exceptions.RequestException('meow')
+        self.assertFalse(
+            self.api_client._do_lookup(self.hardware_info,
+                                       node_uuid=None))
+        self.assertEqual(1, mock_log.exception.call_count)
+
+    @mock.patch.object(ironic_api_client, 'LOG', autospec=True)
+    def test_do_lookup_unknown_exception_fallback(self, mock_log):
+        mock_log.exception.side_effect = TypeError
+        self.api_client.session.request = mock.Mock()
+        self.api_client.session.request.side_effect = \
+            requests.exceptions.RequestException('meow')
+        self.assertRaises(errors.LookupNodeError,
+                          self.api_client._do_lookup,
+                          self.hardware_info,
+                          node_uuid=None)
+        self.assertEqual(1, mock_log.exception.call_count)
+        self.assertEqual(2, mock_log.error.call_count)
+
     def test_do_lookup_bad_response_code(self):
         response = FakeResponse(status_code=400, content={
             'node': {
diff --git a/releasenotes/notes/fixes-agent-lookup-retries-1b4bb90b8e783aca.yaml b/releasenotes/notes/fixes-agent-lookup-retries-1b4bb90b8e783aca.yaml
new file mode 100644
index 000000000..057765013
--- /dev/null
+++ b/releasenotes/notes/fixes-agent-lookup-retries-1b4bb90b8e783aca.yaml
@@ -0,0 +1,9 @@
+---
+fixes:
+  - |
+    Fixes retry logic issues with the Agent Lookup which can result in
+    the lookup failing prematurely before being completed, typically
+    resulting in an abrupt end to the agent logging and potentially
+    weird errors like TypeError being reported on the agent process
+    standard error output. For more information see
+    `bug 2007968 <https://storyboard.openstack.org/#!/story/2007968>`_.