diff --git a/codex-rs/app-server-protocol/schema/json/EventMsg.json b/codex-rs/app-server-protocol/schema/json/EventMsg.json
index 39af1ac96d..2cfbd74840 100644
--- a/codex-rs/app-server-protocol/schema/json/EventMsg.json
+++ b/codex-rs/app-server-protocol/schema/json/EventMsg.json
@@ -544,6 +544,13 @@
         }
       ]
     },
+    "EscalationStatus": {
+      "enum": [
+        "approved",
+        "rejected"
+      ],
+      "type": "string"
+    },
     "EventMsg": {
       "description": "Response event from the agent NOTE: Make sure none of these values have optional types, as it will mess up the extension code-gen.",
       "oneOf": [
@@ -5914,6 +5921,16 @@
             "id": {
               "type": "string"
             },
+            "metadata": {
+              "anyOf": [
+                {
+                  "$ref": "#/definitions/UserMessageMetadata"
+                },
+                {
+                  "type": "null"
+                }
+              ]
+            },
             "type": {
               "enum": [
                 "UserMessage"
@@ -6236,6 +6253,90 @@
         }
       ]
     },
+    "UserMessageMetadata": {
+      "properties": {
+        "escalation_status": {
+          "anyOf": [
+            {
+              "$ref": "#/definitions/EscalationStatus"
+            },
+            {
+              "type": "null"
+            }
+          ]
+        },
+        "is_plan_mode": {
+          "type": [
+            "boolean",
+            "null"
+          ]
+        },
+        "is_tool_call_escalated": {
+          "type": [
+            "boolean",
+            "null"
+          ]
+        },
+        "personality": {
+          "anyOf": [
+            {
+              "$ref": "#/definitions/UserMessagePersonality"
+            },
+            {
+              "type": "null"
+            }
+          ]
+        },
+        "sandbox_policy": {
+          "anyOf": [
+            {
+              "$ref": "#/definitions/UserMessageSandboxPolicy"
+            },
+            {
+              "type": "null"
+            }
+          ]
+        },
+        "user_message_type": {
+          "anyOf": [
+            {
+              "$ref": "#/definitions/UserMessageType"
+            },
+            {
+              "type": "null"
+            }
+          ]
+        }
+      },
+      "type": "object"
+    },
+    "UserMessagePersonality": {
+      "enum": [
+        "friendly",
+        "pragmatic"
+      ],
+      "type": "string"
+    },
+    "UserMessageSandboxPolicy": {
+      "enum": [
+        "read_only",
+        "sandbox",
+        "full_access"
+      ],
+      "type": "string"
+    },
+    "UserMessageType": {
+      "enum": [
+        "prompt",
+        "prompt_steering",
+        "prompt_queued",
+        "prompt_with_ide_context",
+        "agents_md_default",
+        "agents_md_custom",
+        "environment_context"
+      ],
+      "type": "string"
+    },
     "WebSearchAction": {
       "oneOf": [
         {
diff --git a/codex-rs/app-server-protocol/schema/json/codex_app_server_protocol.schemas.json b/codex-rs/app-server-protocol/schema/json/codex_app_server_protocol.schemas.json
index ff9f8d7d3b..15a5bdbadd 100644
--- a/codex-rs/app-server-protocol/schema/json/codex_app_server_protocol.schemas.json
+++ b/codex-rs/app-server-protocol/schema/json/codex_app_server_protocol.schemas.json
@@ -1774,6 +1774,13 @@
       "title": "DynamicToolCallResponse",
       "type": "object"
     },
+    "EscalationStatus": {
+      "enum": [
+        "approved",
+        "rejected"
+      ],
+      "type": "string"
+    },
     "EventMsg": {
       "$schema": "http://json-schema.org/draft-07/schema#",
       "description": "Response event from the agent NOTE: Make sure none of these values have optional types, as it will mess up the extension code-gen.",
@@ -7290,6 +7297,16 @@
             "id": {
               "type": "string"
             },
+            "metadata": {
+              "anyOf": [
+                {
+                  "$ref": "#/definitions/UserMessageMetadata"
+                },
+                {
+                  "type": "null"
+                }
+              ]
+            },
             "type": {
               "enum": [
                 "UserMessage"
@@ -7487,6 +7504,90 @@
         }
       ]
     },
+    "UserMessageMetadata": {
+      "properties": {
+        "escalation_status": {
+          "anyOf": [
+            {
+              "$ref": "#/definitions/EscalationStatus"
+            },
+            {
+              "type": "null"
+            }
+          ]
+        },
+        "is_plan_mode": {
+          "type": [
+            "boolean",
+            "null"
+          ]
+        },
+        "is_tool_call_escalated": {
+          "type": [
+            "boolean",
+            "null"
+          ]
+        },
+        "personality": {
+          "anyOf": [
+            {
+              "$ref": "#/definitions/UserMessagePersonality"
+            },
+            {
+              "type": "null"
+            }
+          ]
+        },
+        "sandbox_policy": {
+          "anyOf": [
+            {
+              "$ref": "#/definitions/UserMessageSandboxPolicy"
+            },
+            {
+              "type": "null"
+            }
+          ]
+        },
+        "user_message_type": {
+          "anyOf": [
+            {
+              "$ref": "#/definitions/UserMessageType"
+            },
+            {
+              "type": "null"
+            }
+          ]
+        }
+      },
+      "type": "object"
+    },
+    "UserMessagePersonality": {
+      "enum": [
+        "friendly",
+        "pragmatic"
+      ],
+      "type": "string"
+    },
+    "UserMessageSandboxPolicy": {
+      "enum": [
+        "read_only",
+        "sandbox",
+        "full_access"
+      ],
+      "type": "string"
+    },
+    "UserMessageType": {
+      "enum": [
+        "prompt",
+        "prompt_steering",
+        "prompt_queued",
+        "prompt_with_ide_context",
+        "agents_md_default",
+        "agents_md_custom",
+        "environment_context"
+      ],
+      "type": "string"
+    },
     "W3cTraceContext": {
       "properties": {
         "traceparent": {
diff --git a/codex-rs/app-server-protocol/schema/json/codex_app_server_protocol.v2.schemas.json b/codex-rs/app-server-protocol/schema/json/codex_app_server_protocol.v2.schemas.json
index da523ea97c..d119bfbd89 100644
--- a/codex-rs/app-server-protocol/schema/json/codex_app_server_protocol.v2.schemas.json
+++ b/codex-rs/app-server-protocol/schema/json/codex_app_server_protocol.v2.schemas.json
@@ -3311,6 +3311,13 @@
       "title": "ErrorNotification",
       "type": "object"
     },
+    "EscalationStatus": {
+      "enum": [
+        "approved",
+        "rejected"
+      ],
+      "type": "string"
+    },
     "EventMsg": {
       "$schema": "http://json-schema.org/draft-07/schema#",
       "description": "Response event from the agent NOTE: Make sure none of these values have optional types, as it will mess up the extension code-gen.",
@@ -13692,6 +13699,16 @@
             "id": {
               "type": "string"
             },
+            "metadata": {
+              "anyOf": [
+                {
+                  "$ref": "#/definitions/UserMessageMetadata"
+                },
+                {
+                  "type": "null"
+                }
+              ]
+            },
             "type": {
               "enum": [
                 "UserMessage"
@@ -14249,6 +14266,90 @@
         }
       ]
     },
+    "UserMessageMetadata": {
+      "properties": {
+        "escalation_status": {
+          "anyOf": [
+            {
+              "$ref": "#/definitions/EscalationStatus"
+            },
+            {
+              "type": "null"
+            }
+          ]
+        },
+        "is_plan_mode": {
+          "type": [
+            "boolean",
+            "null"
+          ]
+        },
+        "is_tool_call_escalated": {
+          "type": [
+            "boolean",
+            "null"
+          ]
+        },
+        "personality": {
+          "anyOf": [
+            {
+              "$ref": "#/definitions/UserMessagePersonality"
+            },
+            {
+              "type": "null"
+            }
+          ]
+        },
+        "sandbox_policy": {
+          "anyOf": [
+            {
+              "$ref": "#/definitions/UserMessageSandboxPolicy"
+            },
+            {
+              "type": "null"
+            }
+          ]
+        },
+        "user_message_type": {
+          "anyOf": [
+            {
+              "$ref": "#/definitions/UserMessageType"
+            },
+            {
+              "type": "null"
+            }
+          ]
+        }
+      },
+      "type": "object"
+    },
+    "UserMessagePersonality": {
+      "enum": [
+        "friendly",
+        "pragmatic"
+      ],
+      "type": "string"
+    },
+    "UserMessageSandboxPolicy": {
+      "enum": [
+        "read_only",
+        "sandbox",
+        "full_access"
+      ],
+      "type": "string"
+    },
+    "UserMessageType": {
+      "enum": [
+        "prompt",
+        "prompt_steering",
+        "prompt_queued",
+        "prompt_with_ide_context",
+        "agents_md_default",
+        "agents_md_custom",
+        "environment_context"
+      ],
+      "type": "string"
+    },
     "Verbosity": {
       "description": "Controls output length/detail on GPT-5 models via the Responses API. Serialized with lowercase values to match the OpenAI API.",
       "enum": [
diff --git a/codex-rs/app-server-protocol/schema/typescript/EscalationStatus.ts b/codex-rs/app-server-protocol/schema/typescript/EscalationStatus.ts
new file mode 100644
index 0000000000..3d7fb95353
--- /dev/null
+++ b/codex-rs/app-server-protocol/schema/typescript/EscalationStatus.ts
@@ -0,0 +1,5 @@
+// GENERATED CODE! DO NOT MODIFY BY HAND!
+
+// This file was generated by [ts-rs](https://github.com/Aleph-Alpha/ts-rs). Do not edit this file manually.
+
+export type EscalationStatus = "approved" | "rejected";
diff --git a/codex-rs/app-server-protocol/schema/typescript/UserMessageItem.ts b/codex-rs/app-server-protocol/schema/typescript/UserMessageItem.ts
index df856287a5..3c2b03bea7 100644
--- a/codex-rs/app-server-protocol/schema/typescript/UserMessageItem.ts
+++ b/codex-rs/app-server-protocol/schema/typescript/UserMessageItem.ts
@@ -2,5 +2,6 @@
 
 // This file was generated by [ts-rs](https://github.com/Aleph-Alpha/ts-rs). Do not edit this file manually.
 import type { UserInput } from "./UserInput";
+import type { UserMessageMetadata } from "./UserMessageMetadata";
 
-export type UserMessageItem = { id: string, content: Array<UserInput>, };
+export type UserMessageItem = { id: string, content: Array<UserInput>, metadata?: UserMessageMetadata, };
diff --git a/codex-rs/app-server-protocol/schema/typescript/UserMessageMetadata.ts b/codex-rs/app-server-protocol/schema/typescript/UserMessageMetadata.ts
new file mode 100644
index 0000000000..b8803b5b1e
--- /dev/null
+++ b/codex-rs/app-server-protocol/schema/typescript/UserMessageMetadata.ts
@@ -0,0 +1,9 @@
+// GENERATED CODE! DO NOT MODIFY BY HAND!
+
+// This file was generated by [ts-rs](https://github.com/Aleph-Alpha/ts-rs). Do not edit this file manually.
+import type { EscalationStatus } from "./EscalationStatus";
+import type { UserMessagePersonality } from "./UserMessagePersonality";
+import type { UserMessageSandboxPolicy } from "./UserMessageSandboxPolicy";
+import type { UserMessageType } from "./UserMessageType";
+
+export type UserMessageMetadata = { is_plan_mode?: boolean, is_tool_call_escalated?: boolean, escalation_status?: EscalationStatus, sandbox_policy?: UserMessageSandboxPolicy, user_message_type?: UserMessageType, personality?: UserMessagePersonality, };
diff --git a/codex-rs/app-server-protocol/schema/typescript/UserMessagePersonality.ts b/codex-rs/app-server-protocol/schema/typescript/UserMessagePersonality.ts
new file mode 100644
index 0000000000..8d0df046e7
--- /dev/null
+++ b/codex-rs/app-server-protocol/schema/typescript/UserMessagePersonality.ts
@@ -0,0 +1,5 @@
+// GENERATED CODE! DO NOT MODIFY BY HAND!
+
+// This file was generated by [ts-rs](https://github.com/Aleph-Alpha/ts-rs). Do not edit this file manually.
+
+export type UserMessagePersonality = "friendly" | "pragmatic";
diff --git a/codex-rs/app-server-protocol/schema/typescript/UserMessageSandboxPolicy.ts b/codex-rs/app-server-protocol/schema/typescript/UserMessageSandboxPolicy.ts
new file mode 100644
index 0000000000..797dbdf309
--- /dev/null
+++ b/codex-rs/app-server-protocol/schema/typescript/UserMessageSandboxPolicy.ts
@@ -0,0 +1,5 @@
+// GENERATED CODE! DO NOT MODIFY BY HAND!
+
+// This file was generated by [ts-rs](https://github.com/Aleph-Alpha/ts-rs). Do not edit this file manually.
+
+export type UserMessageSandboxPolicy = "read_only" | "sandbox" | "full_access";
diff --git a/codex-rs/app-server-protocol/schema/typescript/UserMessageType.ts b/codex-rs/app-server-protocol/schema/typescript/UserMessageType.ts
new file mode 100644
index 0000000000..ad1cac24ea
--- /dev/null
+++ b/codex-rs/app-server-protocol/schema/typescript/UserMessageType.ts
@@ -0,0 +1,5 @@
+// GENERATED CODE! DO NOT MODIFY BY HAND!
+
+// This file was generated by [ts-rs](https://github.com/Aleph-Alpha/ts-rs). Do not edit this file manually.
+
+export type UserMessageType = "prompt" | "prompt_steering" | "prompt_queued" | "prompt_with_ide_context" | "agents_md_default" | "agents_md_custom" | "environment_context";
diff --git a/codex-rs/app-server-protocol/schema/typescript/index.ts b/codex-rs/app-server-protocol/schema/typescript/index.ts
index fd0d333e4a..8353f6fc83 100644
--- a/codex-rs/app-server-protocol/schema/typescript/index.ts
+++ b/codex-rs/app-server-protocol/schema/typescript/index.ts
@@ -50,6 +50,7 @@ export type { DynamicToolCallRequest } from "./DynamicToolCallRequest";
 export type { DynamicToolCallResponseEvent } from "./DynamicToolCallResponseEvent";
 export type { ElicitationRequestEvent } from "./ElicitationRequestEvent";
 export type { ErrorEvent } from "./ErrorEvent";
+export type { EscalationStatus } from "./EscalationStatus";
 export type { EventMsg } from "./EventMsg";
 export type { ExecApprovalRequestEvent } from "./ExecApprovalRequestEvent";
 export type { ExecCommandApprovalParams } from "./ExecCommandApprovalParams";
@@ -205,6 +206,10 @@ export type { UpdatePlanArgs } from "./UpdatePlanArgs";
 export type { UserInput } from "./UserInput";
 export type { UserMessageEvent } from "./UserMessageEvent";
 export type { UserMessageItem } from "./UserMessageItem";
+export type { UserMessageMetadata } from "./UserMessageMetadata";
+export type { UserMessagePersonality } from "./UserMessagePersonality";
+export type { UserMessageSandboxPolicy } from "./UserMessageSandboxPolicy";
+export type { UserMessageType } from "./UserMessageType";
 export type { Verbosity } from "./Verbosity";
 export type { ViewImageToolCallEvent } from "./ViewImageToolCallEvent";
 export type { WarningEvent } from "./WarningEvent";