diff --git a/src/main/ipc/pty.test.ts b/src/main/ipc/pty.test.ts
index 47c4fb06b10..573ed990ad4 100644
--- a/src/main/ipc/pty.test.ts
+++ b/src/main/ipc/pty.test.ts
@@ -3934,6 +3934,52 @@ describe('registerPtyHandlers', () => {
     )
   })
 
+  it('removes the previous orphan-cleanup listener from its original webContents', () => {
+    const firstWindow = {
+      isDestroyed: () => false,
+      webContents: {
+        on: vi.fn(),
+        send: vi.fn(),
+        removeListener: vi.fn()
+      }
+    }
+    const secondWindow = {
+      isDestroyed: () => false,
+      webContents: {
+        on: vi.fn(),
+        send: vi.fn(),
+        removeListener: vi.fn()
+      }
+    }
+
+    registerPtyHandlers(firstWindow as never)
+    const didFinishLoad = firstWindow.webContents.on.mock.calls.find(
+      ([eventName]) => eventName === 'did-finish-load'
+    )?.[1] as (() => void) | undefined
+    expect(didFinishLoad).toBeTypeOf('function')
+
+    setLocalPtyProvider({
+      spawn: vi.fn(),
+      write: vi.fn(),
+      resize: vi.fn(),
+      kill: vi.fn(),
+      shutdown: vi.fn(),
+      onData: vi.fn(() => vi.fn()),
+      onExit: vi.fn(() => vi.fn()),
+      listProcesses: vi.fn(async () => []),
+      getForegroundProcess: vi.fn(async () => null)
+    } as never)
+    registerPtyHandlers(secondWindow as never)
+
+    expect(firstWindow.webContents.removeListener).toHaveBeenCalledWith(
+      'did-finish-load',
+      didFinishLoad
+    )
+    expect(
+      secondWindow.webContents.on.mock.calls.some(([eventName]) => eventName === 'did-finish-load')
+    ).toBe(false)
+  })
+
   it('clears PTY state even when kill reports the process is already gone', async () => {
     const proc = {
       onData: vi.fn(() => makeDisposable()),
diff --git a/src/main/ipc/pty.ts b/src/main/ipc/pty.ts
index f5a91782295..b2535a4a3dc 100644
--- a/src/main/ipc/pty.ts
+++ b/src/main/ipc/pty.ts
@@ -848,6 +848,7 @@ export function setPtyOwnership(id: string, connectionId: string | null): void {
 let localDataUnsub: (() => void) | null = null
 let localExitUnsub: (() => void) | null = null
 let didFinishLoadHandler: (() => void) | null = null
+let didFinishLoadWebContents: WebContents | null = null
 
 // Why: the "Restart daemon" path needs to re-bind provider→renderer listeners
 // against the freshly-created adapter after replaceDaemonProvider swaps the
@@ -861,6 +862,14 @@ export function rebindLocalProviderListeners(): void {
   rebindProviderListeners?.()
 }
 
+function clearDidFinishLoadHandler(): void {
+  if (didFinishLoadHandler && didFinishLoadWebContents) {
+    didFinishLoadWebContents.removeListener('did-finish-load', didFinishLoadHandler)
+  }
+  didFinishLoadHandler = null
+  didFinishLoadWebContents = null
+}
+
 // Why: the "Restart daemon" flow needs to detach listeners from the current
 // adapter *after* synthetic pty:exit events fan out (so the renderer receives
 // them) but *before* replaceDaemonProvider swaps in the new adapter (so the
@@ -1388,11 +1397,9 @@ export function registerPtyHandlers(
   // Why: only applies to LocalPtyProvider where PTYs live in the Electron main
   // process and can become orphaned on page reload. Daemon-backed sessions
   // survive renderer restarts by design — orphan cleanup would kill them.
+  clearDidFinishLoadHandler()
   if (localProvider instanceof LocalPtyProvider) {
     const lp = localProvider
-    if (didFinishLoadHandler) {
-      mainWindow.webContents.removeListener('did-finish-load', didFinishLoadHandler)
-    }
     didFinishLoadHandler = () => {
       const killed = lp.killOrphanedPtys(lp.advanceGeneration() - 1)
       for (const { id } of killed) {
@@ -1402,6 +1409,7 @@ export function registerPtyHandlers(
         runtime?.onPtyExit(id, -1)
       }
     }
+    didFinishLoadWebContents = mainWindow.webContents
     mainWindow.webContents.on('did-finish-load', didFinishLoadHandler)
   }