diff --git a/cli/.pylintrc b/cli/.pylintrc
index 691ed1ec..48366260 100644
--- a/cli/.pylintrc
+++ b/cli/.pylintrc
@@ -4,4 +4,5 @@ good-names = k, v
 [MESSAGES CONTROL]
 # We currently have some older systems running this which
 # don't support f-strings yet
-disable = C0209
+# Disable too-many-lines check because pylint on github seems to be miscounting lines in __init__.py
+disable = C0209,too-many-lines
diff --git a/cli/testflinger_cli/__init__.py b/cli/testflinger_cli/__init__.py
index 821b02fb..603c722e 100644
--- a/cli/testflinger_cli/__init__.py
+++ b/cli/testflinger_cli/__init__.py
@@ -156,6 +156,11 @@ def __init__(self):
             or self.config.get("secret_key")
             or os.environ.get("TESTFLINGER_SECRET_KEY")
         )
+        error_threshold = self.config.get(
+            "error_threshold"
+            or os.environ.get("TESTFLINGER_ERROR_THRESHOLD")
+            or 3
+        )
 
         # Allow config subcommand without worrying about server or client
         if (
@@ -168,7 +173,7 @@ def __init__(self):
                 'Server must start with "http://" or "https://" '
                 '- currently set to: "{}"'.format(server)
             )
-        self.client = client.Client(server)
+        self.client = client.Client(server, error_threshold=error_threshold)
 
     def run(self):
         """Run the subcommand specified in command line arguments"""
@@ -361,7 +366,12 @@ def status(self):
         job_state = self.get_job_state(self.args.job_id)
         if job_state != "unknown":
             self.history.update(self.args.job_id, job_state)
-        print(job_state)
+            print(job_state)
+        else:
+            print(
+                "Unable to retrieve job state from the server, check your "
+                "connection or try again later."
+            )
 
     def cancel(self, job_id=None):
         """Tell the server to cancel a specified JOB_ID"""
@@ -980,8 +990,8 @@ def get_job_state(self, job_id):
                     "Received 404 error from server. Are you "
                     "sure this is a testflinger server?"
                 )
-        except (IOError, ValueError):
+        except (IOError, ValueError) as exc:
             # For other types of network errors, or JSONDecodeError if we got
             # a bad return from get_status()
-            logger.warning("Unable to retrieve job state.")
+            logger.debug("Unable to retrieve job state: %s", exc)
         return "unknown"
diff --git a/cli/testflinger_cli/client.py b/cli/testflinger_cli/client.py
index a82bb1a0..635b7824 100644
--- a/cli/testflinger_cli/client.py
+++ b/cli/testflinger_cli/client.py
@@ -43,8 +43,10 @@ def __init__(self, status, msg=""):
 class Client:
     """Testflinger connection client"""
 
-    def __init__(self, server):
+    def __init__(self, server, error_threshold=3):
         self.server = server
+        self.error_count = 0
+        self.error_threshold = error_threshold
 
     def get(self, uri_frag, timeout=15, headers=None):
         """Submit a GET request to the server
@@ -56,14 +58,16 @@ def get(self, uri_frag, timeout=15, headers=None):
         uri = urllib.parse.urljoin(self.server, uri_frag)
         try:
             req = requests.get(uri, timeout=timeout, headers=headers)
-        except requests.exceptions.ConnectionError:
-            logger.error("Unable to communicate with specified server.")
-            raise
-        except IOError:
-            # This should catch all other timeout cases
-            logger.error(
-                "Timeout while trying to communicate with the server."
-            )
+            self.error_count = 0
+        except (IOError, requests.exceptions.ConnectionError) as exc:
+            self.error_count += 1
+            if self.error_count % self.error_threshold == 0:
+                logger.warning(
+                    "Error communicating with the server for the past %s "
+                    "requests, but will continue to retry. Last error: %s",
+                    self.error_count,
+                    exc,
+                )
             raise
         if req.status_code != 200:
             raise HTTPError(req.status_code)
diff --git a/cli/testflinger_cli/tests/test_client.py b/cli/testflinger_cli/tests/test_client.py
new file mode 100644
index 00000000..466c9824
--- /dev/null
+++ b/cli/testflinger_cli/tests/test_client.py
@@ -0,0 +1,47 @@
+# Copyright (C) 2024 Canonical
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU General Public License as published by
+# the Free Software Foundation, either version 3 of the License, or
+# (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with this program.  If not, see <http://www.gnu.org/licenses/>.
+#
+
+"""
+Unit tests for the Client class
+"""
+
+import logging
+import pytest
+import requests
+
+from testflinger_cli.client import Client
+
+
+def test_get_error_threshold(caplog, requests_mock):
+    """Test that a warning is logged when error_threshold is reached"""
+    caplog.set_level(logging.WARNING)
+    requests_mock.get(
+        "http://testflinger/test", exc=requests.exceptions.ConnectionError
+    )
+    client = Client("http://testflinger", error_threshold=3)
+    for _ in range(2):
+        with pytest.raises(requests.exceptions.ConnectionError):
+            client.get("test")
+        assert (
+            "Error communicating with the server for the past"
+            not in caplog.text
+        )
+    with pytest.raises(requests.exceptions.ConnectionError):
+        client.get("test")
+    assert (
+        "Error communicating with the server for the past 3 requests"
+        in caplog.text
+    )
diff --git a/docs/reference/cli-config.rst b/docs/reference/cli-config.rst
new file mode 100644
index 00000000..bdb9bd71
--- /dev/null
+++ b/docs/reference/cli-config.rst
@@ -0,0 +1,47 @@
+Command Line Interface Configuration
+====================================
+
+The Testflinger CLI can be configured on the command line using the parameters described in ``testflinger --help``. However, sometimes it also supports using environment variables, or reading values from a configuration file. This can be helpful for CI/CD environments, or for setting up a config with different default values read from a config file.
+
+The configuration file is read from ``$XDG_CONFIG_HOME/testflinger-cli.conf`` by default, but this can be overridden with the ``--configfile`` parameter.
+
+When a configuration variable is defined in multiple locations, Testflinger resolves the value by applying the following priority order, from highest to lowest:
+
+1. command-line parameter (for example, ``--server <local_server>``)
+
+2. configuration file
+
+3. environment variable
+
+You can show the current values stored in the config file by running ``testflinger config``. If no value is found on the command line, config file, or environment variable, then a safe default value will be used.
+
+To set a configuration value in the config file, you can edit it directly or use ``testflinger config key=value``.
+
+Testflinger Config Variables
+----------------------------
+
+The following config values are currently supported:
+
+* server - Testflinger Server URL to use
+
+  * Config file key: ``server``
+  * Environment variable: ``TESTFLINGER_SERVER``
+  * Default: ``https://testflinger.canonical.com``
+
+* error_threshold - warn the user of possible server/network problems after failing to read from the server after this many consecutive attempts
+
+  * Config file key: ``error_threshold``
+  * Environment variable: ``TESTFLINGER_ERROR_THRESHOLD``
+  * Default: ``3``
+
+* client_id - Client ID to use for APIs that require authorisation
+
+  * Config file key: ``client_id``
+  * Environment variable: ``TESTFLINGER_CLIENT_ID``
+  * Default: ``None``
+
+* secret_key - Secret key to use for APIs that require authorisation
+
+  * Config file key: ``secret_key``
+  * Environment variable: ``TESTFLINGER_SECRET_KEY``
+  * Default: ``None``
diff --git a/docs/reference/index.rst b/docs/reference/index.rst
index efc8047a..d82ce0b3 100644
--- a/docs/reference/index.rst
+++ b/docs/reference/index.rst
@@ -23,4 +23,12 @@ Working with Testflinger servers and agents
 
     testflinger-server-conf
     testflinger-agent-conf
-    test-phases
\ No newline at end of file
+    test-phases
+
+Using the Command Line Interface
+--------------------------------
+
+.. toctree::
+    :maxdepth: 1
+
+    cli-config
\ No newline at end of file