diff --git a/src/renderer/src/components/browser-pane/BrowserPane.tsx b/src/renderer/src/components/browser-pane/BrowserPane.tsx
index 5a0cb9d0615..0e786d64544 100644
--- a/src/renderer/src/components/browser-pane/BrowserPane.tsx
+++ b/src/renderer/src/components/browser-pane/BrowserPane.tsx
@@ -2632,6 +2632,7 @@ function RemoteBrowserPagePane({
           onClick={() => (markup.isActive ? markup.cancel() : void markup.start())}
           disabled={!frameUrl}
           active={markup.isActive}
+          surfaceActive={isActive}
           className="h-7 w-7"
         />
       </div>
@@ -5122,6 +5123,7 @@ function BrowserPagePane({
             onClick={() => (markup.isActive ? markup.cancel() : void markup.start())}
             disabled={isBlankTab || grab.state !== 'idle'}
             active={markup.isActive}
+            surfaceActive={isActive}
           />
 
           <Button
diff --git a/src/renderer/src/components/browser-pane/markup/MarkupDrawButton.tsx b/src/renderer/src/components/browser-pane/markup/MarkupDrawButton.tsx
index bc2b2be8c03..ec700170eb7 100644
--- a/src/renderer/src/components/browser-pane/markup/MarkupDrawButton.tsx
+++ b/src/renderer/src/components/browser-pane/markup/MarkupDrawButton.tsx
@@ -1,6 +1,8 @@
-import React from 'react'
+import React, { useEffect } from 'react'
 import { PenTool } from 'lucide-react'
+import { Badge } from '@/components/ui/badge'
 import { Button } from '@/components/ui/button'
+import { Popover, PopoverContent, PopoverTrigger } from '@/components/ui/popover'
 import { Tooltip, TooltipContent, TooltipTrigger } from '@/components/ui/tooltip'
 import { cn } from '@/lib/utils'
 import { translate } from '@/i18n/i18n'
@@ -10,6 +12,12 @@ export type MarkupDrawButtonProps = {
   onClick: () => void
   disabled?: boolean
   active?: boolean
+  /**
+   * The browser pane's isActive. Required (no default) so every caller must
+   * decide explicitly — inactive/hidden tabs cannot force-open a portaled
+   * layer against a zero-size trigger (which lands at the viewport origin).
+   */
+  surfaceActive: boolean
   className?: string
 }
 
@@ -19,45 +27,134 @@ export function MarkupDrawButton({
   onClick,
   disabled,
   active,
+  surfaceActive,
   className
 }: MarkupDrawButtonProps): React.JSX.Element {
   const label = translate('auto.components.browser-pane.markup.drawButton', 'Draw on screenshot')
-  // Why: nudge the button the first time it's usable so users discover the tool.
-  const { hintOpen, dismissHint } = useMarkupDrawHint(!disabled && !active)
+  // Why: nudge the button the first time it's usable on a visible surface so
+  // users discover the tool without pinning a tooltip to a hidden pane.
+  const { hintOpen, dismissHint } = useMarkupDrawHint(surfaceActive && !disabled && !active)
+  // Why: close synchronously off the same `surfaceActive` render instead of
+  // waiting on the hook's effect — BrowserPane sets inert/hidden on the pane
+  // in the same commit isActive flips, so a one-tick delay would let the
+  // popover anchor briefly against an already-hidden trigger.
+  const showHint = hintOpen && surfaceActive
+
+  // Why: Electron <webview> clicks never reach the renderer document, so
+  // Radix outside-click dismiss misses them. Window blur covers focus leaving
+  // the renderer into the guest (same pattern as BrowserImportHintButton).
+  useEffect(() => {
+    if (!showHint) {
+      return
+    }
+    window.addEventListener('blur', dismissHint)
+    return () => window.removeEventListener('blur', dismissHint)
+  }, [dismissHint, showHint])
+
+  const startMarkup = (): void => {
+    dismissHint()
+    onClick()
+  }
+
+  const button = (
+    <Button
+      size="icon"
+      variant={active ? 'default' : 'ghost'}
+      className={cn(
+        className ?? 'h-8 w-8',
+        active && 'bg-foreground/80 text-background hover:bg-foreground/90',
+        // Why: soft ring while the discovery callout is open — points at the
+        // control without the harsh solid highlight of a force-open tooltip.
+        showHint && 'ring-2 ring-ring/45 ring-offset-1 ring-offset-background'
+      )}
+      onClick={startMarkup}
+      disabled={disabled}
+      aria-label={label}
+      aria-pressed={active}
+    >
+      <PenTool className="size-4" />
+    </Button>
+  )
+
+  // Discovery uses a dismissable popover (outside click / Escape / blur / act)
+  // instead of a force-open tooltip — tooltips stay stuck when controlled open
+  // and mis-position against hidden triggers. Styled like BrowserImportHint
+  // (surface + title + body + actions), not an inverted tooltip chip.
+  //
+  // Why: Popover and Tooltip stay mounted as one persistent tree (matching
+  // WorkspaceStatusAppearancePopover's Tooltip-wrapping-Popover pattern)
+  // instead of switching root element types on `hintOpen` — swapping roots
+  // would unmount/remount the trigger button at the exact moments the hint
+  // is meant to draw the user's attention to it.
   return (
-    <Tooltip open={hintOpen ? true : undefined}>
-      <TooltipTrigger asChild>
-        {/* Why: wrap in a span so tooltip hover still fires when disabled. */}
-        <span className="inline-flex">
-          <Button
-            size="icon"
-            variant={active ? 'default' : 'ghost'}
-            className={cn(
-              className ?? 'h-8 w-8',
-              active && 'bg-foreground/80 text-background hover:bg-foreground/90',
-              // Why: ring the button while the one-time discovery hint is open.
-              hintOpen && 'ring-2 ring-ring ring-offset-1 ring-offset-background'
-            )}
-            onClick={() => {
-              dismissHint()
-              onClick()
-            }}
-            disabled={disabled}
-            aria-label={label}
-            aria-pressed={active}
-          >
-            <PenTool className="size-4" />
-          </Button>
-        </span>
-      </TooltipTrigger>
-      <TooltipContent side="bottom" sideOffset={4}>
-        {hintOpen
-          ? translate(
-              'auto.components.browser-pane.markup.drawHint',
-              'New — draw on the page, then copy it to your agent'
-            )
-          : label}
-      </TooltipContent>
-    </Tooltip>
+    <Popover
+      modal={false}
+      open={showHint}
+      onOpenChange={(open) => {
+        if (!open) {
+          dismissHint()
+        }
+      }}
+    >
+      <Tooltip>
+        <TooltipTrigger asChild>
+          <PopoverTrigger asChild>
+            {/* Why: wrap in a span so the trigger still fires when disabled. */}
+            <span className="inline-flex">{button}</span>
+          </PopoverTrigger>
+        </TooltipTrigger>
+        <TooltipContent side="bottom" sideOffset={4}>
+          {label}
+        </TooltipContent>
+      </Tooltip>
+      <PopoverContent
+        side="bottom"
+        align="center"
+        sideOffset={6}
+        className="w-72 p-3"
+        onOpenAutoFocus={(event) => {
+          // Why: don't steal focus from the address bar / webview on first show.
+          event.preventDefault()
+        }}
+      >
+        <div className="space-y-3">
+          <div className="space-y-1.5">
+            <div className="flex items-center gap-2">
+              <Badge
+                variant="secondary"
+                className="h-5 shrink-0 px-1.5 text-[10px] font-semibold tracking-wider uppercase"
+              >
+                {translate('auto.components.browser-pane.markup.drawHintBadge', 'New')}
+              </Badge>
+              <div className="text-sm font-medium text-foreground">{label}</div>
+            </div>
+            <p className="text-xs leading-5 text-muted-foreground">
+              {translate(
+                'auto.components.browser-pane.markup.drawHint',
+                'Draw on the page, then copy the markup to paste into your agent.'
+              )}
+            </p>
+          </div>
+          <div className="flex items-center gap-3">
+            <Button
+              type="button"
+              size="sm"
+              className="h-7 gap-1.5 px-2.5 text-xs"
+              onClick={startMarkup}
+            >
+              <PenTool className="size-3.5" />
+              {translate('auto.components.browser-pane.markup.drawHintTry', 'Try it')}
+            </Button>
+            <button
+              type="button"
+              onClick={dismissHint}
+              className="rounded-sm text-xs text-muted-foreground hover:text-foreground focus-visible:ring-1 focus-visible:ring-ring focus-visible:outline-none"
+            >
+              {translate('auto.components.browser-pane.markup.drawHintDismiss', 'Got it')}
+            </button>
+          </div>
+        </div>
+      </PopoverContent>
+    </Popover>
   )
 }
diff --git a/src/renderer/src/components/browser-pane/markup/use-markup-draw-hint.test.ts b/src/renderer/src/components/browser-pane/markup/use-markup-draw-hint.test.ts
new file mode 100644
index 00000000000..309a109b03b
--- /dev/null
+++ b/src/renderer/src/components/browser-pane/markup/use-markup-draw-hint.test.ts
@@ -0,0 +1,61 @@
+/** @vitest-environment happy-dom */
+import { act, renderHook } from '@testing-library/react'
+import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest'
+
+const HINT_KEY = 'orca.browser.markup-draw-hint-seen'
+
+vi.mock('@/store', () => ({
+  useAppStore: (selector: (state: { persistedUIReady: boolean }) => unknown) =>
+    selector({ persistedUIReady: true })
+}))
+
+import { useMarkupDrawHint } from './use-markup-draw-hint'
+
+describe('useMarkupDrawHint', () => {
+  beforeEach(() => {
+    window.localStorage.removeItem(HINT_KEY)
+  })
+
+  afterEach(() => {
+    window.localStorage.removeItem(HINT_KEY)
+  })
+
+  it('opens once when eligible and records the seen flag', () => {
+    const { result } = renderHook(() => useMarkupDrawHint(true))
+
+    expect(result.current.hintOpen).toBe(true)
+    expect(window.localStorage.getItem(HINT_KEY)).toBe('true')
+  })
+
+  it('does not open when the surface is not eligible', () => {
+    const { result } = renderHook(() => useMarkupDrawHint(false))
+
+    expect(result.current.hintOpen).toBe(false)
+    expect(window.localStorage.getItem(HINT_KEY)).toBeNull()
+  })
+
+  it('closes when eligibility drops so a hidden pane cannot keep it open', () => {
+    const { result, rerender } = renderHook(({ eligible }) => useMarkupDrawHint(eligible), {
+      initialProps: { eligible: true }
+    })
+
+    expect(result.current.hintOpen).toBe(true)
+
+    rerender({ eligible: false })
+    expect(result.current.hintOpen).toBe(false)
+  })
+
+  it('dismisses without reopening after the first view', () => {
+    const first = renderHook(() => useMarkupDrawHint(true))
+    expect(first.result.current.hintOpen).toBe(true)
+
+    act(() => {
+      first.result.current.dismissHint()
+    })
+    expect(first.result.current.hintOpen).toBe(false)
+    first.unmount()
+
+    const second = renderHook(() => useMarkupDrawHint(true))
+    expect(second.result.current.hintOpen).toBe(false)
+  })
+})
diff --git a/src/renderer/src/components/browser-pane/markup/use-markup-draw-hint.ts b/src/renderer/src/components/browser-pane/markup/use-markup-draw-hint.ts
index f6d1ab2257e..7709c196984 100644
--- a/src/renderer/src/components/browser-pane/markup/use-markup-draw-hint.ts
+++ b/src/renderer/src/components/browser-pane/markup/use-markup-draw-hint.ts
@@ -2,11 +2,13 @@ import { useCallback, useEffect, useState } from 'react'
 import { useAppStore } from '@/store'
 
 // One-time discovery highlight for the screenshot-markup Draw button. Shows once
-// per install — the first time the button is usable — so users notice the new
-// tool. Gated on its own localStorage flag (not a contextual tour), so it fires
-// for everyone, including users who already finished the capped browser tour.
-// It stays open until the user acts (clicks Draw) or the button stops being
-// usable; there is no auto-timeout.
+// per install — the first time the button is usable and its surface is active —
+// so users notice the new tool. Gated on its own localStorage flag (not a
+// contextual tour), so it fires for everyone, including users who already
+// finished the capped browser tour.
+//
+// Stays open until the user dismisses it (outside click / Escape / blur), clicks
+// Draw, or the button stops being eligible. No auto-timeout.
 const MARKUP_DRAW_HINT_SEEN_KEY = 'orca.browser.markup-draw-hint-seen'
 
 // Records the first-ever view and returns whether this call is that first view.
@@ -31,9 +33,10 @@ export function useMarkupDrawHint(eligible: boolean): MarkupDrawHint {
   const [hintOpen, setHintOpen] = useState(false)
 
   useEffect(() => {
-    // Why: only nudge once the app is ready and the button is usable. If it stops
-    // being usable while showing (grab started, markup open, blank tab), close it
-    // so the forced-open tooltip can't get stuck over a now-disabled button.
+    // Why: only nudge once the app is ready and the button is usable on a
+    // visible surface. If eligibility drops mid-hint (tab switch, grab
+    // started, markup open, blank tab), close it so a forced-open floating
+    // layer can't stick over a hidden or disabled control at (0,0).
     if (!persistedUIReady || !eligible) {
       setHintOpen(false)
       return
diff --git a/src/renderer/src/i18n/locales/en.json b/src/renderer/src/i18n/locales/en.json
index 904551378c9..257200dcc77 100644
--- a/src/renderer/src/i18n/locales/en.json
+++ b/src/renderer/src/i18n/locales/en.json
@@ -13028,7 +13028,10 @@
           "copiedToast": "Markup copied — paste it into your agent ({{value0}})",
           "copy": "Copy Markup",
           "drawButton": "Draw on screenshot",
-          "drawHint": "New — draw on the page, then copy it to your agent",
+          "drawHint": "Draw on the page, then copy the markup to paste into your agent.",
+          "drawHintBadge": "New",
+          "drawHintDismiss": "Got it",
+          "drawHintTry": "Try it",
           "errorAttach": "Could not attach the markup screenshot.",
           "errorCapture": "Could not capture the page to draw on.",
           "errorUnavailable": "Screenshot markup is not available on this page.",
diff --git a/src/renderer/src/i18n/locales/es.json b/src/renderer/src/i18n/locales/es.json
index 4561dd25d61..5c0fc46acc2 100644
--- a/src/renderer/src/i18n/locales/es.json
+++ b/src/renderer/src/i18n/locales/es.json
@@ -13028,7 +13028,10 @@
           "copiedToast": "Marcado copiado: pégalo en tu agente ({{value0}})",
           "copy": "Copiar marcado",
           "drawButton": "Dibujar en la captura",
-          "drawHint": "Nuevo: dibuja en la página y cópialo en tu agente",
+          "drawHint": "Dibuja en la página y copia el markup para pegarlo en tu agente.",
+          "drawHintBadge": "Nuevo",
+          "drawHintDismiss": "Entendido",
+          "drawHintTry": "Probar",
           "errorAttach": "No se pudo adjuntar la captura de pantalla con marcado.",
           "errorCapture": "No se pudo capturar la página para dibujar.",
           "errorUnavailable": "El marcado de captura de pantalla no está disponible en esta página.",
diff --git a/src/renderer/src/i18n/locales/ja.json b/src/renderer/src/i18n/locales/ja.json
index f012157d588..75efd9ce994 100644
--- a/src/renderer/src/i18n/locales/ja.json
+++ b/src/renderer/src/i18n/locales/ja.json
@@ -13028,7 +13028,10 @@
           "copiedToast": "注釈をコピーしました — エージェントに貼り付けてください（{{value0}}）",
           "copy": "注釈をコピー",
           "drawButton": "スクリーンショットに描き込み",
-          "drawHint": "新機能 — ページに描き込み、エージェントに貼り付けられます",
+          "drawHint": "ページに描き込み、マークアップをコピーしてエージェントに貼り付けられます。",
+          "drawHintBadge": "新機能",
+          "drawHintDismiss": "了解",
+          "drawHintTry": "試してみる",
           "errorAttach": "注釈付きスクリーンショットを添付できませんでした。",
           "errorCapture": "描画用にページを取得できませんでした。",
           "errorUnavailable": "このページではスクリーンショット注釈を利用できません。",
diff --git a/src/renderer/src/i18n/locales/ko.json b/src/renderer/src/i18n/locales/ko.json
index 2fae5839230..2ddefe47f79 100644
--- a/src/renderer/src/i18n/locales/ko.json
+++ b/src/renderer/src/i18n/locales/ko.json
@@ -13028,7 +13028,10 @@
           "copiedToast": "마크업을 복사했습니다 — 에이전트에 붙여넣으세요 ({{value0}})",
           "copy": "마크업 복사",
           "drawButton": "스크린샷에 그리기",
-          "drawHint": "새 기능 — 페이지에 그린 다음 에이전트에 붙여넣으세요",
+          "drawHint": "페이지에 그린 다음 마크업을 복사해 에이전트에 붙여넣으세요.",
+          "drawHintBadge": "새 기능",
+          "drawHintDismiss": "확인",
+          "drawHintTry": "사용해 보기",
           "errorAttach": "마크업 스크린샷을 첨부하지 못했습니다.",
           "errorCapture": "그릴 페이지를 캡처하지 못했습니다.",
           "errorUnavailable": "이 페이지에서는 스크린샷 마크업을 사용할 수 없습니다.",
diff --git a/src/renderer/src/i18n/locales/zh.json b/src/renderer/src/i18n/locales/zh.json
index e23f6853fe3..9e74716b26a 100644
--- a/src/renderer/src/i18n/locales/zh.json
+++ b/src/renderer/src/i18n/locales/zh.json
@@ -13028,7 +13028,10 @@
           "copiedToast": "已复制标注 — 粘贴到你的智能体（{{value0}}）",
           "copy": "复制标注",
           "drawButton": "在截图上绘制",
-          "drawHint": "新功能 — 在页面上绘制，然后复制到你的智能体",
+          "drawHint": "在页面上绘制，然后复制标记并粘贴到你的智能体。",
+          "drawHintBadge": "新功能",
+          "drawHintDismiss": "知道了",
+          "drawHintTry": "试一试",
           "errorAttach": "无法附加标注后的截图。",
           "errorCapture": "无法捕获页面进行绘制。",
           "errorUnavailable": "此页面无法使用截图标注。",