diff --git a/src/frontend/src/features/pip/components/PictureInPicturePortal.tsx b/src/frontend/src/features/pip/components/PictureInPicturePortal.tsx
index 00cb20b8..326e40a3 100644
--- a/src/frontend/src/features/pip/components/PictureInPicturePortal.tsx
+++ b/src/frontend/src/features/pip/components/PictureInPicturePortal.tsx
@@ -4,6 +4,7 @@ import { UNSAFE_PortalProvider } from '@react-aria/overlays'
 import { documentPictureInPictureStore } from '@/stores/documentPictureInPicture'
 import { useSnapshot } from 'valtio'
 import { useEffect, useMemo } from 'react'
+import { CrossDocumentOverlaysContext } from '@/primitives/CrossDocumentOverlaysContext'
 
 const InternalPortal = ({ children }: { children: React.ReactNode }) => {
   const pipStoreSnap = useSnapshot(documentPictureInPictureStore)
@@ -32,7 +33,11 @@ const InternalPortal = ({ children }: { children: React.ReactNode }) => {
      * instead.
      */
     <UNSAFE_PortalProvider getContainer={() => container}>
-      {children}
+      {/*React Aria computes overlay position based on the main window size, so*/}
+      {/*we must disable it to position overlays correctly across documents.*/}
+      <CrossDocumentOverlaysContext.Provider value={true}>
+        {children}
+      </CrossDocumentOverlaysContext.Provider>
     </UNSAFE_PortalProvider>,
     container
   )
diff --git a/src/frontend/src/features/pip/components/controls/PipOptionsMenuItems.tsx b/src/frontend/src/features/pip/components/controls/PipOptionsMenuItems.tsx
index a2834183..7991c066 100644
--- a/src/frontend/src/features/pip/components/controls/PipOptionsMenuItems.tsx
+++ b/src/frontend/src/features/pip/components/controls/PipOptionsMenuItems.tsx
@@ -1,9 +1,6 @@
 import { Menu as RACMenu, MenuItem } from 'react-aria-components'
 import { PictureInPictureMenuItem } from '@/features/rooms/livekit/components/controls/Options/PictureInPictureMenuItem'
-import {
-  CollapsibleControl,
-  CollapsibleControls,
-} from '../PipControlBar'
+import { CollapsibleControl, CollapsibleControls } from '../PipControlBar'
 import { RiArrowUpLine, RiEmotionLine, RiHand } from '@remixicon/react'
 import { menuRecipe } from '@/primitives/menuRecipe.ts'
 import { useReactionsToolbar } from '@/features/reactions/hooks/useReactionsToolbar'
diff --git a/src/frontend/src/primitives/CrossDocumentOverlaysContext.tsx b/src/frontend/src/primitives/CrossDocumentOverlaysContext.tsx
new file mode 100644
index 00000000..c52b9253
--- /dev/null
+++ b/src/frontend/src/primitives/CrossDocumentOverlaysContext.tsx
@@ -0,0 +1,15 @@
+import { createContext, useContext } from 'react'
+
+/**
+ * Signals that React Aria's default overlay positioning can't be trusted in
+ * this subtree because the trigger and the rendered overlay live in different
+ * documents (currently: picture-in-picture windows) — React Aria measures
+ * against the main window's viewport, so tooltips, popovers, and menus end up
+ * mispositioned in the host that actually displays them. When `true`, consumers
+ * should bypass React Aria's positioning and handle placement themselves
+ * (e.g. a visual-only tooltip); triggers should still carry an accessible name.
+ */
+export const CrossDocumentOverlaysContext = createContext(false)
+
+export const useCrossDocumentOverlays = () =>
+  useContext(CrossDocumentOverlaysContext)
diff --git a/src/frontend/src/primitives/TooltipWrapper.tsx b/src/frontend/src/primitives/TooltipWrapper.tsx
index 86ac105f..c918e666 100644
--- a/src/frontend/src/primitives/TooltipWrapper.tsx
+++ b/src/frontend/src/primitives/TooltipWrapper.tsx
@@ -6,6 +6,8 @@ import {
   type TooltipProps,
 } from 'react-aria-components'
 import { styled } from '@/styled-system/jsx'
+import { useCrossDocumentOverlays } from '@/primitives/CrossDocumentOverlaysContext'
+import { VisualOnlyTooltip } from '@/primitives/VisualOnlyTooltip'
 
 export type TooltipWrapperProps = {
   tooltip?: string
@@ -24,13 +26,18 @@ export const TooltipWrapper = ({
 }: {
   children: ReactNode
 } & TooltipWrapperProps) => {
-  return tooltip ? (
+  const isCrossDocumentOverlays = useCrossDocumentOverlays()
+
+  if (!tooltip) return children
+
+  if (isCrossDocumentOverlays)
+    return <VisualOnlyTooltip tooltip={tooltip}>{children}</VisualOnlyTooltip>
+
+  return (
     <TooltipTrigger delay={tooltipType === 'instant' ? 150 : 1000}>
       {children}
       <Tooltip>{tooltip}</Tooltip>
     </TooltipTrigger>
-  ) : (
-    children
   )
 }
 
diff --git a/src/frontend/src/primitives/VisualOnlyTooltip.tsx b/src/frontend/src/primitives/VisualOnlyTooltip.tsx
index 1d196f77..4f97bc11 100644
--- a/src/frontend/src/primitives/VisualOnlyTooltip.tsx
+++ b/src/frontend/src/primitives/VisualOnlyTooltip.tsx
@@ -1,15 +1,18 @@
 import {
-  type ReactElement,
   cloneElement,
   isValidElement,
+  useLayoutEffect,
+  useMemo,
   useRef,
   useState,
+  ReactNode,
 } from 'react'
 import { createPortal } from 'react-dom'
 import { css } from '@/styled-system/css'
+import { useUNSAFE_PortalContext } from '@react-aria/overlays'
 
 export type VisualOnlyTooltipProps = {
-  children: ReactElement
+  children: ReactNode
   tooltip: string
   ariaLabel?: string
   tooltipPosition?: 'top' | 'bottom'
@@ -32,19 +35,29 @@ export const VisualOnlyTooltip = ({
   tooltipPosition = 'top',
 }: VisualOnlyTooltipProps) => {
   const [isVisible, setIsVisible] = useState(false)
+  const { getContainer } = useUNSAFE_PortalContext()
   const wrapperRef = useRef<HTMLDivElement>(null)
+  const tooltipRef = useRef<HTMLDivElement>(null)
   const [position, setPosition] = useState<{
     top: number
     left: number
   } | null>(null)
+  const [computedStyle, setComputedStyle] = useState<{
+    left: number
+    arrowLeft: number
+  } | null>(null)
 
-  const isBottom = tooltipPosition === 'bottom'
+  const [effectiveBottom, setEffectiveBottom] = useState(
+    tooltipPosition === 'bottom'
+  )
 
   const showTooltip = () => {
     if (!wrapperRef.current) return
     const rect = wrapperRef.current.getBoundingClientRect()
+    const preferBottom = tooltipPosition === 'bottom'
+    setEffectiveBottom(preferBottom)
     setPosition({
-      top: isBottom ? rect.bottom + 8 : rect.top - 8,
+      top: preferBottom ? rect.bottom + 8 : rect.top - 8,
       left: rect.left + rect.width / 2,
     })
     setIsVisible(true)
@@ -53,15 +66,67 @@ export const VisualOnlyTooltip = ({
   const hideTooltip = () => {
     setIsVisible(false)
     setPosition(null)
+    setComputedStyle(null)
   }
 
-  const tooltipData = isVisible && position ? { isVisible, position } : null
+  useLayoutEffect(() => {
+    if (!tooltipRef.current || !wrapperRef.current || !isVisible || !position)
+      return
+    const tooltipRect = tooltipRef.current.getBoundingClientRect()
+    const triggerRect = wrapperRef.current.getBoundingClientRect()
+    const doc = tooltipRef.current.ownerDocument
+    const viewportWidth = doc.defaultView?.innerWidth ?? globalThis.innerWidth
+    const padding = 8
+
+    // Vertical flip: if tooltip overflows the top, switch to bottom
+    if (!effectiveBottom && position.top - tooltipRect.height < 0) {
+      const flippedTop = triggerRect.bottom + 8
+      setEffectiveBottom(true)
+      setPosition({ top: flippedTop, left: position.left })
+      return
+    }
+
+    // Horizontal clamping (both edges)
+    const desiredLeft = position.left - tooltipRect.width / 2
+    const minLeft = padding
+    const maxLeft = viewportWidth - padding - tooltipRect.width
+
+    if (desiredLeft >= minLeft && desiredLeft <= maxLeft) {
+      setComputedStyle(null)
+      return
+    }
+
+    const clampedLeft = Math.max(minLeft, Math.min(maxLeft, desiredLeft))
+    setComputedStyle({
+      left: clampedLeft,
+      arrowLeft: position.left - clampedLeft,
+    })
+  }, [isVisible, position, effectiveBottom])
+
+  const portalContainer = useMemo(() => {
+    if (getContainer) return getContainer()
+    return wrapperRef.current?.ownerDocument?.body ?? document.body
+  }, [getContainer])
   const wrappedChild = isValidElement(children)
     ? cloneElement(children, {
         ...(ariaLabel ? { 'aria-label': ariaLabel } : {}),
       })
     : children
 
+  const translateY = effectiveBottom ? 'translateY(0)' : 'translateY(-100%)'
+  const translateXY = effectiveBottom
+    ? 'translate(-50%, 0)'
+    : 'translate(-50%, -100%)'
+
+  const tooltipInlineStyle: React.CSSProperties & Record<string, string> = {
+    top: `${position?.top}px`,
+    left: computedStyle ? `${computedStyle.left}px` : `${position?.left}px`,
+    transform: computedStyle ? translateY : translateXY,
+    ...(computedStyle
+      ? { '--tooltip-arrow-left': `${computedStyle.arrowLeft}px` }
+      : null),
+  }
+
   return (
     <>
       <div
@@ -73,11 +138,14 @@ export const VisualOnlyTooltip = ({
       >
         {wrappedChild}
       </div>
-      {tooltipData &&
+      {isVisible &&
+        position &&
+        portalContainer &&
         createPortal(
           <div
             aria-hidden="true"
             role="presentation"
+            ref={tooltipRef}
             className={css({
               position: 'fixed',
               padding: '2px 8px',
@@ -87,15 +155,15 @@ export const VisualOnlyTooltip = ({
               fontSize: 14,
               whiteSpace: 'nowrap',
               pointerEvents: 'none',
-              zIndex: 9999,
+              zIndex: 100001,
               boxShadow: '0 8px 20px rgba(0 0 0 / 0.1)',
               '&::after': {
                 content: '""',
                 position: 'absolute',
-                left: '50%',
+                left: 'var(--tooltip-arrow-left, 50%)',
                 transform: 'translateX(-50%)',
                 border: '4px solid transparent',
-                ...(isBottom
+                ...(effectiveBottom
                   ? {
                       bottom: '100%',
                       borderBottomColor: 'primaryDark.100',
@@ -106,17 +174,11 @@ export const VisualOnlyTooltip = ({
                     }),
               },
             })}
-            style={{
-              top: `${tooltipData.position.top}px`,
-              left: `${tooltipData.position.left}px`,
-              transform: isBottom
-                ? 'translate(-50%, 0)'
-                : 'translate(-50%, -100%)',
-            }}
+            style={tooltipInlineStyle}
           >
             {tooltip}
           </div>,
-          document.body
+          portalContainer
         )}
     </>
   )