diff --git a/desktop/electron/main.ts b/desktop/electron/main.ts
index 5be323cb..ec234056 100644
--- a/desktop/electron/main.ts
+++ b/desktop/electron/main.ts
@@ -36,6 +36,7 @@ import { writeWindowSmokeSnapshot } from './services/windowSmoke'
 import {
   installWindowLifecycle,
   readWindowState,
+  refreshWindowsDragHitTest,
   restoreWindowMaximized,
   saveWindowState,
   showMainWindow,
@@ -385,6 +386,7 @@ async function createMainWindow() {
 
   restoreWindowMaximized(mainWindow, restoredState)
   showMainWindow(mainWindow, app)
+  refreshWindowsDragHitTest(mainWindow, process.platform)
   writeWindowSmokeSnapshot(mainWindow, 'after-final-show')
 }
 
diff --git a/desktop/electron/services/windows.test.ts b/desktop/electron/services/windows.test.ts
index 74d25e5b..ea8fc240 100644
--- a/desktop/electron/services/windows.test.ts
+++ b/desktop/electron/services/windows.test.ts
@@ -11,6 +11,7 @@ import {
   isPersistableWindowState,
   isWindowStateVisibleOnAnyDisplay,
   readWindowState,
+  refreshWindowsDragHitTest,
   restoreWindowMaximized,
   showMainWindow,
   toggleWindowFullScreen,
@@ -143,6 +144,71 @@ describe('Electron window service', () => {
     })
   })
 
+  it('refreshes Windows drag hit testing after the first frameless show', () => {
+    vi.useFakeTimers()
+    try {
+      const bounds = { x: 20, y: 30, width: 1280, height: 820 }
+      const window = {
+        isDestroyed: () => false,
+        isMinimized: () => false,
+        isMaximized: () => false,
+        isFullScreen: () => false,
+        getBounds: vi.fn(() => bounds),
+        setBounds: vi.fn(),
+      }
+
+      const cancel = refreshWindowsDragHitTest(window as never, 'win32', 100)
+
+      expect(cancel).toEqual(expect.any(Function))
+      expect(window.setBounds).not.toHaveBeenCalled()
+
+      vi.advanceTimersByTime(100)
+
+      expect(window.getBounds).toHaveBeenCalledTimes(1)
+      expect(window.setBounds).toHaveBeenNthCalledWith(1, { ...bounds, height: bounds.height + 1 })
+      expect(window.setBounds).toHaveBeenNthCalledWith(2, bounds)
+    } finally {
+      vi.useRealTimers()
+    }
+  })
+
+  it('does not refresh drag hit testing outside Windows', () => {
+    vi.useFakeTimers()
+    try {
+      const window = {
+        setBounds: vi.fn(),
+      }
+
+      expect(refreshWindowsDragHitTest(window as never, 'darwin', 100)).toBeUndefined()
+      vi.advanceTimersByTime(100)
+      expect(window.setBounds).not.toHaveBeenCalled()
+    } finally {
+      vi.useRealTimers()
+    }
+  })
+
+  it('skips the Windows drag hit-test refresh after the window is destroyed', () => {
+    vi.useFakeTimers()
+    try {
+      const window = {
+        isDestroyed: () => true,
+        isMinimized: () => false,
+        isMaximized: () => false,
+        isFullScreen: () => false,
+        getBounds: vi.fn(() => ({ x: 20, y: 30, width: 1280, height: 820 })),
+        setBounds: vi.fn(),
+      }
+
+      refreshWindowsDragHitTest(window as never, 'win32', 100)
+      vi.advanceTimersByTime(100)
+
+      expect(window.getBounds).not.toHaveBeenCalled()
+      expect(window.setBounds).not.toHaveBeenCalled()
+    } finally {
+      vi.useRealTimers()
+    }
+  })
+
   it('shows, restores, and focuses the hidden main window when a tray or notification action reopens it', () => {
     const window = {
       isVisible: () => false,
diff --git a/desktop/electron/services/windows.ts b/desktop/electron/services/windows.ts
index 435383ff..4f8996fc 100644
--- a/desktop/electron/services/windows.ts
+++ b/desktop/electron/services/windows.ts
@@ -214,6 +214,31 @@ export function showMainWindow(window: BrowserWindow | null, app?: MacOsWindowVi
   window.focus()
 }
 
+export function refreshWindowsDragHitTest(
+  window: BrowserWindow,
+  platform: NodeJS.Platform = process.platform,
+  delayMs = 100,
+): (() => void) | undefined {
+  if (platform !== 'win32') return undefined
+
+  const timer = setTimeout(() => {
+    if (
+      window.isDestroyed()
+      || window.isMinimized()
+      || window.isMaximized()
+      || window.isFullScreen()
+    ) {
+      return
+    }
+
+    const bounds = window.getBounds()
+    window.setBounds({ ...bounds, height: bounds.height + 1 })
+    window.setBounds(bounds)
+  }, delayMs)
+
+  return () => clearTimeout(timer)
+}
+
 export function installWindowLifecycle({
   app,
   window,
diff --git a/desktop/src/components/chat/PlanModePermissionDialog.test.tsx b/desktop/src/components/chat/PlanModePermissionDialog.test.tsx
index 458639fd..1ea8781d 100644
--- a/desktop/src/components/chat/PlanModePermissionDialog.test.tsx
+++ b/desktop/src/components/chat/PlanModePermissionDialog.test.tsx
@@ -188,4 +188,30 @@ describe('plan mode permission UI', () => {
     expect(container.textContent).toContain('/tmp/claude-plan.md')
     expect(container.textContent).not.toContain('Tool Output')
   })
+
+  it('renders EnterPlanMode as a compact status instead of raw model instructions', () => {
+    const { container } = render(
+      <ToolCallBlock
+        toolName="EnterPlanMode"
+        input={{}}
+        result={{
+          isError: false,
+          content: [
+            'Entered plan mode. You should now focus on exploring the codebase and designing an implementation approach.',
+            '',
+            'In plan mode, you should:',
+            '1. Thoroughly explore the codebase',
+            '2. Ask clarifying questions if needed',
+            '',
+            'Remember: DO NOT write or edit files until the user approves your plan.',
+          ].join('\n'),
+        }}
+      />,
+    )
+
+    expect(container.textContent).toContain('Plan mode')
+    expect(container.textContent).not.toContain('Tool Output')
+    expect(container.textContent).not.toContain('Thoroughly explore the codebase')
+    expect(container.textContent).not.toContain('Remember: DO NOT write or edit files')
+  })
 })
diff --git a/desktop/src/components/chat/PlanModePreview.tsx b/desktop/src/components/chat/PlanModePreview.tsx
index 4b1b9299..116bc136 100644
--- a/desktop/src/components/chat/PlanModePreview.tsx
+++ b/desktop/src/components/chat/PlanModePreview.tsx
@@ -3,6 +3,7 @@ import { MarkdownRenderer } from '../markdown/MarkdownRenderer'
 import type { PermissionUpdate } from '../../types/chat'
 
 export const EXIT_PLAN_MODE_TOOL_NAME = 'ExitPlanMode'
+export const ENTER_PLAN_MODE_TOOL_NAME = 'EnterPlanMode'
 
 export type AllowedPrompt = {
   tool: string
@@ -28,6 +29,10 @@ export function isExitPlanModeTool(toolName: string): boolean {
   return toolName === EXIT_PLAN_MODE_TOOL_NAME
 }
 
+export function isEnterPlanModeTool(toolName: string): boolean {
+  return toolName === ENTER_PLAN_MODE_TOOL_NAME
+}
+
 export function PlanPreviewCard({
   title,
   plan,
diff --git a/desktop/src/components/chat/ToolCallBlock.tsx b/desktop/src/components/chat/ToolCallBlock.tsx
index 4a320c8a..33294f00 100644
--- a/desktop/src/components/chat/ToolCallBlock.tsx
+++ b/desktop/src/components/chat/ToolCallBlock.tsx
@@ -8,7 +8,12 @@ import { useTranslation } from '../../i18n'
 import type { TranslationKey } from '../../i18n'
 import { InlineImageGallery } from './InlineImageGallery'
 import type { AgentTaskNotification } from '../../types/chat'
-import { PlanPreviewCard, extractPlanPreview, isExitPlanModeTool } from './PlanModePreview'
+import {
+  PlanPreviewCard,
+  extractPlanPreview,
+  isEnterPlanModeTool,
+  isExitPlanModeTool,
+} from './PlanModePreview'
 
 type Props = {
   toolName: string
@@ -46,8 +51,9 @@ type ContentStats = {
 }
 
 export const ToolCallBlock = memo(function ToolCallBlock({ toolName, input, result, compact = false, isPending = false, status, partialInput }: Props) {
-  const isPlanTool = isExitPlanModeTool(toolName)
-  const [expanded, setExpanded] = useState(isPlanTool)
+  const isExitPlanTool = isExitPlanModeTool(toolName)
+  const isEnterPlanTool = isEnterPlanModeTool(toolName)
+  const [expanded, setExpanded] = useState(isExitPlanTool)
   const t = useTranslation()
   const obj = input && typeof input === 'object' ? (input as Record<string, unknown>) : {}
   const icon = TOOL_ICONS[toolName] || 'build'
@@ -78,7 +84,17 @@ export const ToolCallBlock = memo(function ToolCallBlock({ toolName, input, resu
   const hasWritePreview = toolName === 'Write' && typeof obj.content === 'string'
   const expandable = hasEditPreview || hasWritePreview || hasResultDetails || Boolean(isPending && partialInput)
 
-  if (isPlanTool) {
+  if (isEnterPlanTool) {
+    return (
+      <EnterPlanModeToolCallBlock
+        result={result}
+        compact={compact}
+        isPending={isPending}
+      />
+    )
+  }
+
+  if (isExitPlanTool) {
     return (
       <PlanToolCallBlock
         input={input}
@@ -175,6 +191,47 @@ export const ToolCallBlock = memo(function ToolCallBlock({ toolName, input, resu
   )
 })
 
+function EnterPlanModeToolCallBlock({
+  result,
+  compact,
+  isPending,
+}: {
+  result?: { content: unknown; isError: boolean } | null
+  compact: boolean
+  isPending: boolean
+}) {
+  const t = useTranslation()
+  const errorText = result?.isError ? extractTextContent(result.content) : null
+
+  return (
+    <div className={`overflow-hidden rounded-lg border border-[var(--color-brand)]/30 bg-[var(--color-surface-container-lowest)] ${
+      compact ? 'mb-0' : 'mb-2'
+    }`}>
+      <div className="flex w-full items-center gap-2 px-3 py-2 text-left">
+        <span className="material-symbols-outlined text-[14px] text-[var(--color-brand)]">architecture</span>
+        <span className="min-w-0 flex-1 truncate text-[12px] font-semibold text-[var(--color-text-primary)]">
+          {t('settings.permissions.plan')}
+        </span>
+        {isPending ? (
+          <span className="inline-flex shrink-0 items-center gap-1 text-[10px] text-[var(--color-outline)]">
+            <LoaderCircle size={12} strokeWidth={2.4} className="animate-spin" aria-hidden="true" />
+            {t('tool.preparingTool')}
+          </span>
+        ) : null}
+        {result?.isError ? (
+          <span className="material-symbols-outlined shrink-0 text-[14px] text-[var(--color-error)]">error</span>
+        ) : null}
+      </div>
+
+      {result?.isError && errorText ? (
+        <div className="border-t border-[var(--color-border)]/60 px-3 py-3">
+          {renderResultOutput(result, errorText, t)}
+        </div>
+      ) : null}
+    </div>
+  )
+}
+
 function PlanToolCallBlock({
   input,
   result,