diff --git a/.github/dependabot.yml b/.github/dependabot.yml
index d8b0bfee0..5bf500ba1 100644
--- a/.github/dependabot.yml
+++ b/.github/dependabot.yml
@@ -9,3 +9,8 @@ updates:
       actions:
         patterns:
           - "*"
+  # Python
+  - package-ecosystem: "pip"
+    directory: "/"
+    schedule:
+      interval: "weekly"
diff --git a/test/auth/unified/mongodb-oidc-no-retry.json b/test/auth/unified/mongodb-oidc-no-retry.json
index 613af8734..9dbe19827 100644
--- a/test/auth/unified/mongodb-oidc-no-retry.json
+++ b/test/auth/unified/mongodb-oidc-no-retry.json
@@ -416,173 +416,6 @@
           }
         }
       ]
-    },
-    {
-      "description": "Read commands should fail if reauthentication fails",
-      "operations": [
-        {
-          "name": "find",
-          "object": "collection0",
-          "arguments": {
-            "filter": {}
-          },
-          "expectResult": []
-        },
-        {
-          "name": "failPoint",
-          "object": "testRunner",
-          "arguments": {
-            "client": "failPointClient",
-            "failPoint": {
-              "configureFailPoint": "failCommand",
-              "mode": {
-                "times": 2
-              },
-              "data": {
-                "failCommands": [
-                  "find",
-                  "saslStart"
-                ],
-                "errorCode": 391
-              }
-            }
-          }
-        },
-        {
-          "name": "find",
-          "object": "collection0",
-          "arguments": {
-            "filter": {}
-          },
-          "expectError": {
-            "errorCode": 391
-          }
-        }
-      ],
-      "expectEvents": [
-        {
-          "client": "client0",
-          "events": [
-            {
-              "commandStartedEvent": {
-                "command": {
-                  "find": "collName",
-                  "filter": {}
-                }
-              }
-            },
-            {
-              "commandSucceededEvent": {
-                "commandName": "find"
-              }
-            },
-            {
-              "commandStartedEvent": {
-                "command": {
-                  "find": "collName",
-                  "filter": {}
-                }
-              }
-            },
-            {
-              "commandFailedEvent": {
-                "commandName": "find"
-              }
-            }
-          ]
-        }
-      ]
-    },
-    {
-      "description": "Write commands should fail if reauthentication fails",
-      "operations": [
-        {
-          "name": "insertOne",
-          "object": "collection0",
-          "arguments": {
-            "document": {
-              "_id": 1,
-              "x": 1
-            }
-          }
-        },
-        {
-          "name": "failPoint",
-          "object": "testRunner",
-          "arguments": {
-            "client": "failPointClient",
-            "failPoint": {
-              "configureFailPoint": "failCommand",
-              "mode": {
-                "times": 2
-              },
-              "data": {
-                "failCommands": [
-                  "insert",
-                  "saslStart"
-                ],
-                "errorCode": 391
-              }
-            }
-          }
-        },
-        {
-          "name": "insertOne",
-          "object": "collection0",
-          "arguments": {
-            "document": {
-              "_id": 2,
-              "x": 2
-            }
-          },
-          "expectError": {
-            "errorCode": 391
-          }
-        }
-      ],
-      "expectEvents": [
-        {
-          "client": "client0",
-          "events": [
-            {
-              "commandStartedEvent": {
-                "command": {
-                  "insert": "collName",
-                  "documents": [
-                    {
-                      "_id": 1,
-                      "x": 1
-                    }
-                  ]
-                }
-              }
-            },
-            {
-              "commandSucceededEvent": {
-                "commandName": "insert"
-              }
-            },
-            {
-              "commandStartedEvent": {
-                "command": {
-                  "insert": "collName",
-                  "documents": [
-                    {
-                      "_id": 2,
-                      "x": 2
-                    }
-                  ]
-                }
-              }
-            },
-            {
-              "commandFailedEvent": {
-                "commandName": "insert"
-              }
-            }
-          ]
-        }
-      ]
     }
   ]
 }
diff --git a/test/auth_oidc/test_auth_oidc.py b/test/auth_oidc/test_auth_oidc.py
index bb0a95028..7ea565935 100644
--- a/test/auth_oidc/test_auth_oidc.py
+++ b/test/auth_oidc/test_auth_oidc.py
@@ -920,7 +920,7 @@ class TestAuthOIDCMachine(OIDCTestBase):
         # Close the client.
         client.close()
 
-    def test_4_reauthentication(self):
+    def test_4_1_reauthentication_succeds(self):
         # Create a ``MongoClient`` configured with a custom OIDC callback that
         # implements the provider logic.
         client = self.create_client()
@@ -942,6 +942,84 @@ class TestAuthOIDCMachine(OIDCTestBase):
         # Close the client.
         client.close()
 
+    def test_4_2_read_commands_fail_if_reauthentication_fails(self):
+        # Create a ``MongoClient`` whose OIDC callback returns one good token and then
+        # bad tokens after the first call.
+        get_token = self.get_token
+
+        class CustomCallback(OIDCCallback):
+            count = 0
+
+            def fetch(self, _):
+                self.count += 1
+                if self.count == 1:
+                    access_token = get_token()
+                else:
+                    access_token = "bad value"
+                return OIDCCallbackResult(access_token=access_token)
+
+        callback = CustomCallback()
+        client = self.create_client(request_cb=callback)
+
+        # Perform a read operation that succeeds.
+        client.test.test.find_one()
+
+        # Set a fail point for the find command.
+        with self.fail_point(
+            {
+                "mode": {"times": 1},
+                "data": {"failCommands": ["find"], "errorCode": 391},
+            }
+        ):
+            # Perform a ``find`` operation that fails.
+            with self.assertRaises(OperationFailure):
+                client.test.test.find_one()
+
+        # Verify that the callback was called 2 times.
+        self.assertEqual(callback.count, 2)
+
+        # Close the client.
+        client.close()
+
+    def test_4_3_write_commands_fail_if_reauthentication_fails(self):
+        # Create a ``MongoClient`` whose OIDC callback returns one good token and then
+        # bad token after the first call.
+        get_token = self.get_token
+
+        class CustomCallback(OIDCCallback):
+            count = 0
+
+            def fetch(self, _):
+                self.count += 1
+                if self.count == 1:
+                    access_token = get_token()
+                else:
+                    access_token = "bad value"
+                return OIDCCallbackResult(access_token=access_token)
+
+        callback = CustomCallback()
+        client = self.create_client(request_cb=callback)
+
+        # Perform an insert operation that succeeds.
+        client.test.test.insert_one({})
+
+        # Set a fail point for the find command.
+        with self.fail_point(
+            {
+                "mode": {"times": 1},
+                "data": {"failCommands": ["insert"], "errorCode": 391},
+            }
+        ):
+            # Perform a ``insert`` operation that fails.
+            with self.assertRaises(OperationFailure):
+                client.test.test.insert_one({})
+
+        # Verify that the callback was called 2 times.
+        self.assertEqual(callback.count, 2)
+
+        # Close the client.
+        client.close()
+
     def test_5_1_azure_with_no_username(self):
         if ENVIRON != "azure":
             raise unittest.SkipTest("Test is only supported on Azure")