diff --git a/packages/kilo-vscode/tests/unit/permission-queue.test.ts b/packages/kilo-vscode/tests/unit/permission-queue.test.ts
new file mode 100644
index 000000000..e1fc36058
--- /dev/null
+++ b/packages/kilo-vscode/tests/unit/permission-queue.test.ts
@@ -0,0 +1,53 @@
+import { describe, expect, it } from "bun:test"
+import { removeSessionPermissions, upsertPermission } from "../../webview-ui/src/context/permission-queue"
+import type { PermissionRequest } from "../../webview-ui/src/types/messages"
+
+const permission = (input: Partial<PermissionRequest> = {}): PermissionRequest => ({
+  id: input.id ?? "perm-1",
+  sessionID: input.sessionID ?? "session-1",
+  toolName: input.toolName ?? "read",
+  patterns: input.patterns ?? ["/tmp/*"],
+  args: input.args ?? {},
+  message: input.message,
+  tool: input.tool,
+})
+
+describe("permission queue", () => {
+  it("appends a new permission id", () => {
+    const result = upsertPermission([], permission({ id: "perm-1" }))
+    expect(result).toHaveLength(1)
+    expect(result[0].id).toBe("perm-1")
+  })
+
+  it("updates an existing permission id instead of duplicating", () => {
+    const existing = permission({ id: "perm-1", toolName: "read", patterns: ["a"] })
+    const incoming = permission({ id: "perm-1", toolName: "write", patterns: ["b"] })
+
+    const result = upsertPermission([existing], incoming)
+
+    expect(result).toHaveLength(1)
+    expect(result[0]).toEqual(incoming)
+  })
+
+  it("keeps other permission entries when updating one id", () => {
+    const first = permission({ id: "perm-1", sessionID: "session-1" })
+    const second = permission({ id: "perm-2", sessionID: "session-2" })
+    const incoming = permission({ id: "perm-1", toolName: "edit" })
+
+    const result = upsertPermission([first, second], incoming)
+
+    expect(result).toHaveLength(2)
+    expect(result.find((item) => item.id === "perm-1")).toEqual(incoming)
+    expect(result.find((item) => item.id === "perm-2")).toEqual(second)
+  })
+
+  it("removes only permissions from the deleted session", () => {
+    const first = permission({ id: "perm-1", sessionID: "session-1" })
+    const second = permission({ id: "perm-2", sessionID: "session-2" })
+    const third = permission({ id: "perm-3", sessionID: "session-1" })
+
+    const result = removeSessionPermissions([first, second, third], "session-1")
+
+    expect(result).toEqual([second])
+  })
+})
diff --git a/packages/kilo-vscode/webview-ui/src/App.tsx b/packages/kilo-vscode/webview-ui/src/App.tsx
index f940c36e4..3578ebb36 100644
--- a/packages/kilo-vscode/webview-ui/src/App.tsx
+++ b/packages/kilo-vscode/webview-ui/src/App.tsx
@@ -50,15 +50,21 @@ export const DataBridge: Component<{ children: any }> = (props) => {
 
   const data = createMemo(() => {
     const id = session.currentSessionID()
-    const msgs = session.allMessages()
-    const parts = session.allParts()
+    const perms = id ? session.permissions().filter((p) => p.sessionID === id) : []
     return {
       session: session.sessions().map((s) => ({ ...s, id: s.id, role: "user" as const })) as unknown as any[],
       session_status: {} as Record<string, any>,
       session_diff: {} as Record<string, any[]>,
-      message: msgs as unknown as Record<string, SDKMessage[]>,
-      part: parts as unknown as Record<string, SDKPart[]>,
-      permission: id ? { [id]: session.permissions() as unknown as any[] } : {},
+      message: id ? { [id]: session.messages() as unknown as SDKMessage[] } : {},
+      part: id
+        ? Object.fromEntries(
+            session
+              .messages()
+              .map((msg) => [msg.id, session.getParts(msg.id) as unknown as SDKPart[]])
+              .filter(([, parts]) => (parts as SDKPart[]).length > 0),
+          )
+        : {},
+      permission: id ? { [id]: perms as unknown as any[] } : {},
     }
   })
 
diff --git a/packages/kilo-vscode/webview-ui/src/components/chat/ChatView.tsx b/packages/kilo-vscode/webview-ui/src/components/chat/ChatView.tsx
index 56db2a1eb..f8e12ebae 100644
--- a/packages/kilo-vscode/webview-ui/src/components/chat/ChatView.tsx
+++ b/packages/kilo-vscode/webview-ui/src/components/chat/ChatView.tsx
@@ -27,7 +27,7 @@ export const ChatView: Component<ChatViewProps> = (props) => {
   const sessionPermissions = () => session.permissions().filter((p) => p.sessionID === id())
 
   const questionRequest = () => sessionQuestions()[0]
-  const permissionRequest = () => sessionPermissions()[0]
+  const permissionRequest = () => sessionPermissions().find((p) => !p.tool)
   const blocked = () => sessionPermissions().length > 0 || sessionQuestions().length > 0
 
   const [responding, setResponding] = createSignal(false)
diff --git a/packages/kilo-vscode/webview-ui/src/context/permission-queue.ts b/packages/kilo-vscode/webview-ui/src/context/permission-queue.ts
new file mode 100644
index 000000000..da977468a
--- /dev/null
+++ b/packages/kilo-vscode/webview-ui/src/context/permission-queue.ts
@@ -0,0 +1,13 @@
+import type { PermissionRequest } from "../types/messages"
+
+export function upsertPermission(list: PermissionRequest[], permission: PermissionRequest) {
+  const idx = list.findIndex((item) => item.id === permission.id)
+  if (idx === -1) return [...list, permission]
+  const next = list.slice()
+  next[idx] = permission
+  return next
+}
+
+export function removeSessionPermissions(list: PermissionRequest[], sessionID: string) {
+  return list.filter((item) => item.sessionID !== sessionID)
+}
diff --git a/packages/kilo-vscode/webview-ui/src/context/session.tsx b/packages/kilo-vscode/webview-ui/src/context/session.tsx
index 3718b6606..00a454de2 100644
--- a/packages/kilo-vscode/webview-ui/src/context/session.tsx
+++ b/packages/kilo-vscode/webview-ui/src/context/session.tsx
@@ -37,6 +37,7 @@ import type {
   ExtensionMessage,
   FileAttachment,
 } from "../types/messages"
+import { removeSessionPermissions, upsertPermission } from "./permission-queue"
 
 // Derive human-readable status from the last streaming part
 function computeStatus(
@@ -508,7 +509,7 @@ export const SessionProvider: ParentComponent = (props) => {
   }
 
   function handlePermissionRequest(permission: PermissionRequest) {
-    setPermissions((prev) => [...prev, permission])
+    setPermissions((prev) => upsertPermission(prev, permission))
   }
 
   function handleQuestionRequest(question: QuestionRequest) {
@@ -603,6 +604,7 @@ export const SessionProvider: ParentComponent = (props) => {
           return next
         })
       }
+      setPermissions((prev) => removeSessionPermissions(prev, sessionID))
       setStatusMap(
         produce((map) => {
           delete map[sessionID]