diff --git a/src/frontend/src/primitives/Menu.tsx b/src/frontend/src/primitives/Menu.tsx
index f6008716..04da8205 100644
--- a/src/frontend/src/primitives/Menu.tsx
+++ b/src/frontend/src/primitives/Menu.tsx
@@ -1,10 +1,16 @@
-import { ReactNode } from 'react'
+import { ReactNode, useMemo } from 'react'
 import { MenuTrigger } from 'react-aria-components'
 import { StyledPopover } from './Popover'
 import { Box } from './Box'
+import {
+  useOverlayBoundaryElement,
+  useOverlayPortalContainer,
+} from './useOverlayPortalContainer'
 
 /**
  * a Menu is a tuple of a trigger component (most usually a Button) that toggles menu items in a tooltip around the trigger
+ *
+ * Uses UNSAFE_PortalProvider context automatically for portal container (no need for UNSTABLE_portalContainer).
  */
 export const Menu = ({
   children,
@@ -16,10 +22,30 @@ export const Menu = ({
   placement?: 'bottom' | 'top' | 'left' | 'right'
 }) => {
   const [trigger, menu] = children
+  const boundaryElement = useOverlayBoundaryElement()
+  const portalContainer = useOverlayPortalContainer()
+  
+  // Detect if we're in PiP: portal container is in a different document than the main window
+  const isInPiP = useMemo(
+    () =>
+      portalContainer &&
+      portalContainer.ownerDocument &&
+      portalContainer.ownerDocument !== document,
+    [portalContainer]
+  )
+
+  // Default placement: 'bottom' in PiP, 'top' elsewhere (to match existing behavior)
+  const defaultPlacement = isInPiP ? 'bottom' : 'top'
+  const shouldFlip = isInPiP ? false : undefined
+
   return (
     <MenuTrigger>
       {trigger}
-      <StyledPopover placement={placement}>
+      <StyledPopover
+        placement={placement ?? defaultPlacement}
+        shouldFlip={shouldFlip}
+        boundaryElement={boundaryElement}
+      >
         <Box size="sm" type="popover" variant={variant}>
           {menu}
         </Box>
diff --git a/src/frontend/src/primitives/Popover.tsx b/src/frontend/src/primitives/Popover.tsx
index 5ccd995f..e875c8a6 100644
--- a/src/frontend/src/primitives/Popover.tsx
+++ b/src/frontend/src/primitives/Popover.tsx
@@ -8,6 +8,7 @@ import {
 } from 'react-aria-components'
 import { styled } from '@/styled-system/jsx'
 import { Box } from './Box'
+import { useOverlayBoundaryElement } from './useOverlayPortalContainer'
 
 export const StyledPopover = styled(RACPopover, {
   base: {
@@ -65,6 +66,8 @@ const StyledOverlayArrow = styled(OverlayArrow, {
  *
  * Note: to show a list of actionable items, like a dropdown menu, prefer using a <Menu> or <Select>.
  * This is here when needing to show unrestricted content in a box.
+ *
+ * Uses UNSAFE_PortalProvider context automatically for portal container (no need for UNSTABLE_portalContainer).
  */
 export const Popover = ({
   children,
@@ -82,10 +85,11 @@ export const Popover = ({
   withArrow?: boolean
 } & Omit<DialogProps, 'children'>) => {
   const [trigger, popoverContent] = children
+  const boundaryElement = useOverlayBoundaryElement()
   return (
     <DialogTrigger>
       {trigger}
-      <StyledPopover>
+      <StyledPopover boundaryElement={boundaryElement}>
         {withArrow && (
           <StyledOverlayArrow variant={variant}>
             <svg width={12} height={12} viewBox="0 0 12 12">
diff --git a/src/frontend/src/primitives/TooltipWrapper.tsx b/src/frontend/src/primitives/TooltipWrapper.tsx
index 86ac105f..825f770e 100644
--- a/src/frontend/src/primitives/TooltipWrapper.tsx
+++ b/src/frontend/src/primitives/TooltipWrapper.tsx
@@ -6,12 +6,17 @@ import {
   type TooltipProps,
 } from 'react-aria-components'
 import { styled } from '@/styled-system/jsx'
+import { useOverlayPortalContainer } from './useOverlayPortalContainer'
+import { VisualOnlyTooltip } from './VisualOnlyTooltip'
 
 export type TooltipWrapperProps = {
   tooltip?: string
   tooltipType?: 'instant' | 'delayed'
 }
 
+const INSTANT_TOOLTIP_DELAY_MS = 150
+const DELAYED_TOOLTIP_DELAY_MS = 1000
+
 /**
  * Wrap a component you want to apply a tooltip on (for example a Button)
  *
@@ -24,11 +29,25 @@ export const TooltipWrapper = ({
 }: {
   children: ReactNode
 } & TooltipWrapperProps) => {
+  const portalContainer = useOverlayPortalContainer()
+  const isExternalDocument =
+    portalContainer && portalContainer.ownerDocument !== document
+
   return tooltip ? (
-    <TooltipTrigger delay={tooltipType === 'instant' ? 150 : 1000}>
-      {children}
-      <Tooltip>{tooltip}</Tooltip>
-    </TooltipTrigger>
+    isExternalDocument ? (
+      <VisualOnlyTooltip tooltip={tooltip}>{children}</VisualOnlyTooltip>
+    ) : (
+      <TooltipTrigger
+        delay={
+          tooltipType === 'instant'
+            ? INSTANT_TOOLTIP_DELAY_MS
+            : DELAYED_TOOLTIP_DELAY_MS
+        }
+      >
+        {children}
+        <Tooltip>{tooltip}</Tooltip>
+      </TooltipTrigger>
+    )
   ) : (
     children
   )
@@ -53,11 +72,11 @@ const StyledTooltip = styled(RACTooltip, {
     fontSize: 14,
     transform: 'translate3d(0, 0, 0)',
     '&[data-placement=top]': {
-      marginBottom: '8px',
+      marginBottom: '2px',
       '--origin': 'translateY(4px)',
     },
     '&[data-placement=bottom]': {
-      marginTop: '8px',
+      marginTop: '2px',
       '--origin': 'translateY(-4px)',
     },
     '&[data-placement=right]': {
diff --git a/src/frontend/src/primitives/VisualOnlyTooltip.tsx b/src/frontend/src/primitives/VisualOnlyTooltip.tsx
index 1d196f77..f65ec3f5 100644
--- a/src/frontend/src/primitives/VisualOnlyTooltip.tsx
+++ b/src/frontend/src/primitives/VisualOnlyTooltip.tsx
@@ -2,11 +2,12 @@ import {
   type ReactElement,
   cloneElement,
   isValidElement,
-  useRef,
+  useMemo, useRef,
   useState,
 } 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
@@ -32,6 +33,7 @@ export const VisualOnlyTooltip = ({
   tooltipPosition = 'top',
 }: VisualOnlyTooltipProps) => {
   const [isVisible, setIsVisible] = useState(false)
+  const { getContainer } = useUNSAFE_PortalContext()
   const wrapperRef = useRef<HTMLDivElement>(null)
   const [position, setPosition] = useState<{
     top: number
@@ -56,6 +58,11 @@ export const VisualOnlyTooltip = ({
   }
 
   const tooltipData = isVisible && position ? { isVisible, position } : null
+
+  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 } : {}),
@@ -73,7 +80,7 @@ export const VisualOnlyTooltip = ({
       >
         {wrappedChild}
       </div>
-      {tooltipData &&
+      {tooltipData && portalContainer &&
         createPortal(
           <div
             aria-hidden="true"
@@ -116,7 +123,7 @@ export const VisualOnlyTooltip = ({
           >
             {tooltip}
           </div>,
-          document.body
+          portalContainer
         )}
     </>
   )
diff --git a/src/frontend/src/primitives/useOverlayPortalContainer.tsx b/src/frontend/src/primitives/useOverlayPortalContainer.tsx
new file mode 100644
index 00000000..2300d85b
--- /dev/null
+++ b/src/frontend/src/primitives/useOverlayPortalContainer.tsx
@@ -0,0 +1,22 @@
+import { useMemo } from 'react'
+import { useUNSAFE_PortalContext } from '@react-aria/overlays'
+
+export const useOverlayPortalContainer = () => {
+  const { getContainer } = useUNSAFE_PortalContext()
+
+  // Read the portal container provided by UNSAFE_PortalProvider.
+  // This is how overlays know which document/window they should render into.
+  // "UNSAFE" means we're overriding the library default container on purpose.
+  return useMemo(() => getContainer?.() ?? undefined, [getContainer])
+}
+
+export const useOverlayBoundaryElement = () => {
+  const portalContainer = useOverlayPortalContainer()
+  return useMemo(() => {
+    // Use the portal container as the positioning boundary.
+    // In PiP this keeps overlays positioned relative to the PiP window.
+    if (portalContainer) return portalContainer
+    return undefined
+  }, [portalContainer])
+}
+