diff --git a/docs/webhook_events.md b/docs/webhook_events.md
index e5b3d5fd5..920ea6902 100644
--- a/docs/webhook_events.md
+++ b/docs/webhook_events.md
@@ -1173,7 +1173,17 @@ If webhook is set to have Event Grid message format then the payload will look a
                 471,
                 472,
                 473,
-                474
+                474,
+                475,
+                476,
+                477,
+                478,
+                479,
+                480,
+                481,
+                482,
+                483,
+                484
             ],
             "title": "ErrorCode"
         },
@@ -1809,7 +1819,17 @@ If webhook is set to have Event Grid message format then the payload will look a
                 471,
                 472,
                 473,
-                474
+                474,
+                475,
+                476,
+                477,
+                478,
+                479,
+                480,
+                481,
+                482,
+                483,
+                484
             ],
             "title": "ErrorCode"
         }
@@ -2744,7 +2764,17 @@ If webhook is set to have Event Grid message format then the payload will look a
                 471,
                 472,
                 473,
-                474
+                474,
+                475,
+                476,
+                477,
+                478,
+                479,
+                480,
+                481,
+                482,
+                483,
+                484
             ],
             "title": "ErrorCode"
         }
@@ -3461,7 +3491,17 @@ If webhook is set to have Event Grid message format then the payload will look a
                 471,
                 472,
                 473,
-                474
+                474,
+                475,
+                476,
+                477,
+                478,
+                479,
+                480,
+                481,
+                482,
+                483,
+                484
             ],
             "title": "ErrorCode"
         },
@@ -5529,7 +5569,17 @@ If webhook is set to have Event Grid message format then the payload will look a
                 471,
                 472,
                 473,
-                474
+                474,
+                475,
+                476,
+                477,
+                478,
+                479,
+                480,
+                481,
+                482,
+                483,
+                484
             ],
             "title": "ErrorCode"
         },
diff --git a/src/ApiService/ApiService/OneFuzzTypes/Enums.cs b/src/ApiService/ApiService/OneFuzzTypes/Enums.cs
index 464f46cf0..7b3904308 100644
--- a/src/ApiService/ApiService/OneFuzzTypes/Enums.cs
+++ b/src/ApiService/ApiService/OneFuzzTypes/Enums.cs
@@ -39,6 +39,7 @@ public enum ErrorCode {
     UNEXPECTED_DATA_SHAPE = 482,
     UNABLE_TO_SEND = 483,
     NODE_DELETED = 484,
+    // NB: if you update this enum, also update enums.py
 }
 
 public enum VmState {
diff --git a/src/pytypes/onefuzztypes/enums.py b/src/pytypes/onefuzztypes/enums.py
index 767509381..9ce9c43f7 100644
--- a/src/pytypes/onefuzztypes/enums.py
+++ b/src/pytypes/onefuzztypes/enums.py
@@ -281,6 +281,17 @@ class ErrorCode(Enum):
     PROXY_FAILED = 472
     INVALID_CONFIGURATION = 473
     UNABLE_TO_CREATE_CONTAINER = 474
+    UNABLE_TO_DOWNLOAD_FILE = 475
+    VM_UPDATE_FAILED = 476
+    UNSUPPORTED_FIELD_OPERATION = 477
+    ADO_VALIDATION_INVALID_PAT = 478
+    ADO_VALIDATION_INVALID_FIELDS = 479
+    GITHUB_VALIDATION_INVALID_PAT = 480
+    GITHUB_VALIDATION_INVALID_REPOSITORY = 481
+    UNEXPECTED_DATA_SHAPE = 482
+    UNABLE_TO_SEND = 483
+    NODE_DELETED = 484
+    # NB: if you update this enum, also update Enums.cs
 
 
 class HeartbeatType(Enum):