diff --git a/.changeset/dismiss-stale-permissions.md b/.changeset/dismiss-stale-permissions.md
new file mode 100644
index 000000000000..0c031b224b22
--- /dev/null
+++ b/.changeset/dismiss-stale-permissions.md
@@ -0,0 +1,5 @@
+---
+"kilo-code": patch
+---
+
+Dismiss stale permission prompts when another view has already answered them.
diff --git a/packages/kilo-vscode/src/kilo-provider/handlers/permission-handler.ts b/packages/kilo-vscode/src/kilo-provider/handlers/permission-handler.ts
index 3344111a175a..d30e3c75f9ca 100644
--- a/packages/kilo-vscode/src/kilo-provider/handlers/permission-handler.ts
+++ b/packages/kilo-vscode/src/kilo-provider/handlers/permission-handler.ts
@@ -35,12 +35,16 @@ export function recoverablePermissions(perms: RecoverablePermission[], tracked:
 }
 
 function isNotFoundError(error: unknown): boolean {
-  if (!error || typeof error !== "object") return false
-  const obj = error as Record<string, unknown>
-  if (obj.name === "NotFoundError") return true
-  if (typeof obj.status === "number" && obj.status === 404) return true
-  const data = obj.data as Record<string, unknown> | undefined
-  return data?.name === "NotFoundError"
+  const record = (value: unknown) =>
+    value && typeof value === "object" ? (value as Record<string, unknown>) : undefined
+  const obj = record(error)
+  if (!obj) return false
+
+  const cause = record(obj.cause)
+  const body = record(cause?.body)
+  return [obj, record(obj.data), cause, body, record(body?.data)].some(
+    (value) => value?.name === "NotFoundError" || value?.status === 404,
+  )
 }
 
 /**
diff --git a/packages/kilo-vscode/tests/unit/permission-recovery.test.ts b/packages/kilo-vscode/tests/unit/permission-recovery.test.ts
index 9f288b1d7d81..754143cc2ed8 100644
--- a/packages/kilo-vscode/tests/unit/permission-recovery.test.ts
+++ b/packages/kilo-vscode/tests/unit/permission-recovery.test.ts
@@ -1,4 +1,4 @@
-import { describe, it, expect } from "bun:test"
+import { describe, it, expect, spyOn } from "bun:test"
 import {
   fetchAndSendPendingPermissions,
   handlePermissionResponse,
@@ -26,6 +26,7 @@ function permissionClient(
   queries: string[],
   saves: unknown[] = [],
   replies: unknown[] = [],
+  errors?: { save?: unknown; reply?: unknown },
 ) {
   return {
     permission: {
@@ -36,10 +37,12 @@ function permissionClient(
       },
       saveAlwaysRules: async (args: unknown) => {
         saves.push(args)
+        if (errors?.save) throw errors.save
         return { data: true }
       },
       reply: async (args: unknown) => {
         replies.push(args)
+        if (errors?.reply) throw errors.reply
         return { data: true }
       },
     },
@@ -51,8 +54,9 @@ function client(
   queries: string[],
   saves: unknown[] = [],
   replies: unknown[] = [],
+  errors?: { save?: unknown; reply?: unknown },
 ): PermissionContext["client"] {
-  return permissionClient(permsPerDir, queries, saves, replies) as unknown as PermissionContext["client"]
+  return permissionClient(permsPerDir, queries, saves, replies, errors) as unknown as PermissionContext["client"]
 }
 
 function ctx(opts: {
@@ -60,13 +64,14 @@ function ctx(opts: {
   dirs?: Map<string, string>
   permsPerDir?: Record<string, ReturnType<typeof pending>[]>
   workspace?: string
+  errors?: { save?: unknown; reply?: unknown }
 }) {
   const messages: unknown[] = []
   const queries: string[] = []
   const saves: unknown[] = []
   const replies: unknown[] = []
   const perms = opts.permsPerDir ?? {}
-  const sdk = client(perms, queries, saves, replies)
+  const sdk = client(perms, queries, saves, replies, opts.errors)
 
   const permDirs = new Map<string, string>()
   const fake: PermissionContext = {
@@ -136,6 +141,57 @@ describe("handlePermissionResponse", () => {
     ])
     expect(replies).toEqual([{ requestID: "p1", reply: "reject", directory: "/workspace/.kilo/worktrees/feature" }])
   })
+
+  it("treats an SDK-wrapped 404 while saving rules as stale", async () => {
+    const error = new Error("Permission request not found: p1", {
+      cause: { status: 404, body: { name: "NotFoundError" } },
+    })
+    const { fake, messages, saves, replies, permDirs } = ctx({ tracked: ["s1"], errors: { save: error } })
+    permDirs.set("p1", "/workspace/.kilo/worktrees/feature")
+
+    await handlePermissionResponse(fake, "p1", "s1", "once", ["bun *"], [])
+
+    expect(saves).toEqual([
+      {
+        requestID: "p1",
+        directory: "/workspace/.kilo/worktrees/feature",
+        approvedAlways: ["bun *"],
+        deniedAlways: [],
+      },
+    ])
+    expect(replies).toEqual([])
+    expect(permDirs.has("p1")).toBe(false)
+    expect(messages).toEqual([{ type: "permissionError", permissionID: "p1", stale: true }])
+  })
+
+  it("treats an SDK-wrapped 404 while replying as stale", async () => {
+    const error = new Error("Permission request not found: p1", {
+      cause: { status: 404, body: { name: "NotFoundError" } },
+    })
+    const { fake, messages, replies, permDirs } = ctx({ tracked: ["s1"], errors: { reply: error } })
+    permDirs.set("p1", "/workspace/.kilo/worktrees/feature")
+
+    await handlePermissionResponse(fake, "p1", "s1", "once", [], [])
+
+    expect(replies).toEqual([{ requestID: "p1", reply: "once", directory: "/workspace/.kilo/worktrees/feature" }])
+    expect(permDirs.has("p1")).toBe(false)
+    expect(messages).toEqual([{ type: "permissionError", permissionID: "p1", stale: true }])
+  })
+
+  it("does not treat other SDK-wrapped errors as stale", async () => {
+    const error = new Error("Internal server error", {
+      cause: { status: 500, body: { name: "InternalServerError" } },
+    })
+    const { fake, messages, permDirs } = ctx({ tracked: ["s1"], errors: { reply: error } })
+    const spy = spyOn(console, "error").mockImplementation(() => {})
+    permDirs.set("p1", "/workspace/.kilo/worktrees/feature")
+
+    await handlePermissionResponse(fake, "p1", "s1", "once", [], [])
+    spy.mockRestore()
+
+    expect(permDirs.has("p1")).toBe(true)
+    expect(messages).toEqual([{ type: "permissionError", permissionID: "p1" }])
+  })
 })
 
 describe("recoverablePermissions", () => {