diff --git a/src/clients/deluge.py b/src/clients/deluge.py
index 2263b8d..7e031b5 100644
--- a/src/clients/deluge.py
+++ b/src/clients/deluge.py
@@ -3,13 +3,17 @@
 import requests
 from pathlib import Path
 
-from ..errors import TorrentClientError
+from ..errors import TorrentClientError, TorrentClientAuthenticationError
 from .torrent_client import TorrentClient
 from requests.exceptions import RequestException
 from requests.structures import CaseInsensitiveDict
 
 
 class Deluge(TorrentClient):
+  ERROR_CODES = {
+    "NO_AUTH": 1,
+  }
+
   def __init__(self, rpc_url):
     super().__init__()
     self._rpc_url = rpc_url
@@ -37,7 +41,7 @@ def get_torrent_info(self, infohash):
       {"hash": infohash},
     ]
 
-    response = self.__request("web.update_ui", params)
+    response = self.__wrap_request("web.update_ui", params)
     if "torrents" in response:
       torrent = response["torrents"].get(infohash)
 
@@ -75,7 +79,7 @@ def inject_torrent(self, source_torrent_infohash, new_torrent_filepath, save_pat
       },
     ]
 
-    new_torrent_infohash = self.__request("core.add_torrent_file", params)
+    new_torrent_infohash = self.__wrap_request("core.add_torrent_file", params)
     newtorrent_label = self.__determine_label(source_torrent_info)
     self.__set_label(new_torrent_infohash, newtorrent_label)
 
@@ -86,6 +90,7 @@ def __authenticate(self):
     if not password:
       raise Exception("You need to define a password in the Deluge RPC URL. (e.g. http://:<PASSWORD>@localhost:8112)")
 
+    # This method specifically cannot use __wrap_request because an auth error would create an infinite loop
     auth_response = self.__request("auth.login", [password])
     if not auth_response:
       raise TorrentClientError("Reached Deluge RPC endpoint but failed to authenticate")
@@ -93,7 +98,7 @@ def __authenticate(self):
     return self.__request("web.connected")
 
   def __is_label_plugin_enabled(self):
-    response = self.__request("core.get_enabled_plugins")
+    response = self.__wrap_request("core.get_enabled_plugins")
 
     return "Label" in response
 
@@ -109,11 +114,18 @@ def __set_label(self, infohash, label):
     if not self._label_plugin_enabled:
       return
 
-    current_labels = self.__request("label.get_labels")
+    current_labels = self.__wrap_request("label.get_labels")
     if label not in current_labels:
-      self.__request("label.add", [label])
+      self.__wrap_request("label.add", [label])
+
+    return self.__wrap_request("label.set_torrent", [infohash, label])
 
-    return self.__request("label.set_torrent", [infohash, label])
+  def __wrap_request(self, method, params=[]):
+    try:
+      return self.__request(method, params)
+    except TorrentClientAuthenticationError:
+      self.__authenticate()
+      return self.__request(method, params)
 
   def __request(self, method, params=[]):
     href, _, _ = self._extract_credentials_from_url(self._rpc_url)
@@ -148,6 +160,8 @@ def __request(self, method, params=[]):
     self.__handle_response_headers(response.headers)
 
     if "error" in json_response and json_response["error"]:
+      if json_response["error"]["code"] == self.ERROR_CODES["NO_AUTH"]:
+        raise TorrentClientAuthenticationError("Failed to authenticate with Deluge")
       raise TorrentClientError(f"Deluge method {method} returned an error: {json_response['error']}")
 
     return json_response["result"]
diff --git a/src/errors.py b/src/errors.py
index 65836eb..ab8c975 100644
--- a/src/errors.py
+++ b/src/errors.py
@@ -50,5 +50,9 @@ class TorrentClientError(Exception):
   pass
 
 
+class TorrentClientAuthenticationError(Exception):
+  pass
+
+
 class TorrentInjectionError(Exception):
   pass
diff --git a/tests/clients/test_deluge.py b/tests/clients/test_deluge.py
index b108e71..da7a6a0 100644
--- a/tests/clients/test_deluge.py
+++ b/tests/clients/test_deluge.py
@@ -14,7 +14,7 @@
   torrent_info_matcher,
 )
 
-from src.errors import TorrentClientError
+from src.errors import TorrentClientError, TorrentClientAuthenticationError
 from src.clients.deluge import Deluge
 
 
@@ -68,6 +68,15 @@ def test_raises_exception_on_failed_auth(self, api_url, deluge_client):
 
       assert "Reached Deluge RPC endpoint but failed to authenticate" in str(excinfo.value)
 
+  def test_raises_exception_on_errored_auth(self, api_url, deluge_client):
+    with requests_mock.Mocker() as m:
+      m.post(api_url, additional_matcher=auth_matcher, json={"error": {"code": 1}})
+
+      with pytest.raises(TorrentClientAuthenticationError) as excinfo:
+        deluge_client.setup()
+
+      assert "Failed to authenticate with Deluge" in str(excinfo.value)
+
   def test_sets_label_plugin_enabled_when_true(self, api_url, deluge_client):
     assert not deluge_client._label_plugin_enabled
 
@@ -188,6 +197,21 @@ def test_returns_completed_if_seeding(self, api_url, deluge_client, torrent_info
 
       assert response["complete"]
 
+  def test_attempts_reauth_if_deluge_cookie_expired(self, api_url, deluge_client, torrent_info_response):
+    with requests_mock.Mocker() as m:
+      m.post(api_url, additional_matcher=torrent_info_matcher, json={"error": {"code": 1}})
+      m.post(api_url, additional_matcher=auth_matcher, json={"result": True}, headers={"Set-Cookie": "supersecret"})
+      m.post(api_url, additional_matcher=connected_matcher, json={"result": True})
+
+      deluge_client._deluge_cookie = None
+      with pytest.raises(TorrentClientAuthenticationError):
+        deluge_client.get_torrent_info("foo")
+
+      assert deluge_client._deluge_cookie is not None
+      assert m.request_history[-3].json()["method"] == "auth.login"
+      assert m.request_history[-2].json()["method"] == "web.connected"
+      assert m.request_history[-1].json()["method"] == "web.update_ui"
+
 
 class TestInjectTorrent(SetupTeardown):
   def test_injects_torrent(self, api_url, deluge_client, torrent_info_response):