diff --git a/pkg/channels/manager_test.go b/pkg/channels/manager_test.go
index 1a783cc3e..6c518780d 100644
--- a/pkg/channels/manager_test.go
+++ b/pkg/channels/manager_test.go
@@ -1214,7 +1214,7 @@ func TestSendWithRetry_ToolCallsPlaceholderDeleteAndFallsThroughToSend(t *testin
 			ChatID:  "123",
 			Raw: map[string]string{
 				"message_kind": "tool_calls",
-				"tool_calls":   `[{"tool_feedback_explanation":"Looking up config","function":{"name":"read_file","arguments":"{}"}}]`,
+				"tool_calls":   `[{"id":"call_1","type":"function","function":{"name":"read_file","arguments":"{}"},"extra_content":{"tool_feedback_explanation":"Looking up config"}}]`,
 			},
 		},
 	})
diff --git a/web/frontend/src/features/chat/assistant-message-state.ts b/web/frontend/src/features/chat/assistant-message-state.ts
index b38b9c3a4..54eb6163f 100644
--- a/web/frontend/src/features/chat/assistant-message-state.ts
+++ b/web/frontend/src/features/chat/assistant-message-state.ts
@@ -1,8 +1,8 @@
 import {
   parseToolCallsFromContent,
   parseToolCallsValue,
-} from "@/features/chat/tool-calls.ts"
-import type { AssistantMessageKind, ChatMessage } from "@/store/chat.ts"
+} from "@/features/chat/tool-calls"
+import type { AssistantMessageKind, ChatMessage } from "@/store/chat"
 
 type AssistantToolCalls = ChatMessage["toolCalls"]
 type ExistingAssistantMessageState = Pick<ChatMessage, "kind" | "toolCalls">
@@ -15,7 +15,7 @@ export interface AssistantMessageCreateState {
 
 export interface AssistantMessageUpdateState {
   content: string
-  kind?: AssistantMessageKind
+  kind: AssistantMessageKind
   toolCalls?: AssistantToolCalls
 }
 
@@ -100,9 +100,13 @@ export function parseAssistantMessageUpdateState(
   if (existing?.toolCalls) {
     return {
       content,
+      kind: existing.kind ?? "normal",
       toolCalls: undefined,
     }
   }
 
-  return { content }
+  return {
+    content,
+    kind: existing?.kind ?? "normal",
+  }
 }
diff --git a/web/frontend/src/features/chat/tool-calls.ts b/web/frontend/src/features/chat/tool-calls.ts
index bf306c5e5..31d685863 100644
--- a/web/frontend/src/features/chat/tool-calls.ts
+++ b/web/frontend/src/features/chat/tool-calls.ts
@@ -14,7 +14,9 @@ function parseLegacyToolFeedbackContent(
   const body = match[2]?.trim() ?? ""
   const codeFence = /```(?:json)?\r?\n([\s\S]*?)\r?\n```/m.exec(body)
   const argumentsText = codeFence?.[1]?.trim() ?? ""
-  const explanation = body.replace(/```(?:json)?\r?\n[\s\S]*?\r?\n```/gm, "").trim()
+  const explanation = body
+    .replace(/```(?:json)?\r?\n[\s\S]*?\r?\n```/gm, "")
+    .trim()
 
   return [
     {