diff --git a/CHANGELOG.md b/CHANGELOG.md
index 58579aa0b..7ede62163 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,7 @@
 
 ### Fixes
 
+- Fix tooltips around inspector dropdowns/popovers without breaking floating menu anchoring.
 - Harden MCP calls with bounded page-tree responses, oversized-result errors, JSON HTTP responses, and stale WebSocket cleanup.
 - Improve Figma boolean imports by preserving XOR operations as editable exclude nodes and falling back to imported fill geometry when boolean path reconstruction cannot produce a path.
 - Preserve rotated Figma transform origins for imported vector nodes.
diff --git a/playwright.config.ts b/playwright.config.ts
index bd8fa684a..b2f7e0549 100644
--- a/playwright.config.ts
+++ b/playwright.config.ts
@@ -33,7 +33,12 @@ export default defineConfig({
     {
       name: 'openpencil-webkit',
       testDir: './tests/e2e',
-      testMatch: '**/*.webkit.spec.ts',
+      testMatch: [
+        '**/*.webkit.spec.ts',
+        '**/design/panel.spec.ts',
+        '**/export/basic.spec.ts',
+        '**/fonts/settings.spec.ts'
+      ],
       use: {
         browserName: 'webkit'
       }
diff --git a/src/components/FontSettings/FontSettingsPopover.vue b/src/components/FontSettings/FontSettingsPopover.vue
index bd48864f8..643467d99 100644
--- a/src/components/FontSettings/FontSettingsPopover.vue
+++ b/src/components/FontSettings/FontSettingsPopover.vue
@@ -1,6 +1,6 @@
 <script setup lang="ts">
 import { PopoverContent, PopoverPortal, PopoverRoot, PopoverTrigger } from 'reka-ui'
-import { onMounted } from 'vue'
+import { onMounted, ref } from 'vue'
 
 import { isTauri } from '@/app/tauri/env'
 import { useFontSettings } from '@/components/FontSettings/use'
@@ -29,6 +29,7 @@ const primaryButton = useButtonUI({
   ui: { base: 'w-full px-2 py-1.5 text-[10px] font-medium disabled:opacity-50' }
 })
 const showDownloadedFonts = isTauri()
+const popoverOpen = ref(false)
 
 const {
   accessState,
@@ -47,14 +48,19 @@ const {
   setGoogleFontsEnabled
 } = useFontSettings()
 
+function setPopoverOpen(value: boolean) {
+  popoverOpen.value = value
+  if (value) void refreshSummary()
+}
+
 onMounted(() => {
   void refreshSummary()
 })
 </script>
 
 <template>
-  <PopoverRoot @update:open="$event && refreshSummary()">
-    <Tip :label="dialogs.fontSettings">
+  <PopoverRoot v-model:open="popoverOpen" @update:open="setPopoverOpen">
+    <Tip :label="dialogs.fontSettings" :disabled="popoverOpen">
       <PopoverTrigger data-test-id="font-settings-trigger" :class="trigger.base">
         <icon-lucide-settings class="size-3.5" />
       </PopoverTrigger>
@@ -62,6 +68,7 @@ onMounted(() => {
 
     <PopoverPortal>
       <PopoverContent
+        data-test-id="font-settings-panel"
         side="left"
         :side-offset="8"
         align="start"
diff --git a/src/components/chat/ProviderSettings/ProviderSettings.vue b/src/components/chat/ProviderSettings/ProviderSettings.vue
index 0740d6205..335ced09c 100644
--- a/src/components/chat/ProviderSettings/ProviderSettings.vue
+++ b/src/components/chat/ProviderSettings/ProviderSettings.vue
@@ -1,15 +1,5 @@
 <script setup lang="ts">
-import {
-  PopoverClose,
-  PopoverContent,
-  PopoverPortal,
-  PopoverRoot,
-  PopoverTrigger,
-  TooltipContent,
-  TooltipPortal,
-  TooltipRoot,
-  TooltipTrigger
-} from 'reka-ui'
+import { PopoverClose, PopoverContent, PopoverPortal, PopoverRoot, PopoverTrigger } from 'reka-ui'
 import { ref } from 'vue'
 import { useI18n } from '@open-pencil/vue'
 
@@ -21,11 +11,10 @@ import ProviderSelectField from '@/components/chat/ProviderSelect/ProviderSelect
 import StockPhotoKeysSection from '@/components/chat/ProviderSettings/StockPhotoKeysSection.vue'
 import { provideProviderSettings } from '@/components/chat/ProviderSettings/context'
 import { usePopoverUI } from '@/components/ui/popover'
-import { useTooltipUI } from '@/components/ui/tooltip'
+import Tip from '@/components/ui/Tip.vue'
 
 const { dialogs } = useI18n()
 const cls = usePopoverUI({ content: 'isolate z-[51] w-64 p-3' })
-const tooltipCls = useTooltipUI({ content: 'animate-in zoom-in-95 fade-in' })
 const popoverOpen = ref(false)
 const providerSettings = provideProviderSettings()
 
@@ -40,53 +29,46 @@ function onInteractOutside(e: Event) {
 </script>
 
 <template>
-  <TooltipRoot :open="popoverOpen ? false : undefined">
-    <PopoverRoot v-model:open="popoverOpen">
-      <TooltipTrigger as-child>
-        <PopoverTrigger as-child>
-          <button
-            data-test-id="provider-settings-trigger"
-            class="rounded p-0.5 text-muted hover:bg-hover hover:text-surface"
-          >
-            <icon-lucide-settings class="size-3" />
-          </button>
-        </PopoverTrigger>
-      </TooltipTrigger>
-      <TooltipPortal>
-        <TooltipContent side="top" :side-offset="4" :class="tooltipCls.content">
-          {{ dialogs.providerSettings }}
-        </TooltipContent>
-      </TooltipPortal>
-
-      <PopoverPortal>
-        <PopoverContent
-          side="top"
-          :side-offset="8"
-          align="end"
-          :collision-padding="16"
-          :avoid-collisions="true"
-          :class="cls.content"
-          @interact-outside="onInteractOutside"
+  <PopoverRoot v-model:open="popoverOpen">
+    <Tip :label="dialogs.providerSettings" :disabled="popoverOpen">
+      <PopoverTrigger as-child>
+        <button
+          data-test-id="provider-settings-trigger"
+          class="rounded p-0.5 text-muted hover:bg-hover hover:text-surface"
         >
-          <div class="flex flex-col gap-2.5">
-            <h3 class="text-[11px] font-semibold text-surface">{{ dialogs.aiProvider }}</h3>
-            <ProviderSelectField test-id="provider-settings-provider" />
-            <MaxTokensSection />
-            <StockPhotoKeysSection />
-            <CustomEndpointSection />
-            <ApiTypeSection />
-            <ApiKeySection />
+          <icon-lucide-settings class="size-3" />
+        </button>
+      </PopoverTrigger>
+    </Tip>
 
-            <PopoverClose
-              class="mt-1 w-full rounded bg-accent px-2 py-1 text-center text-[11px] font-medium text-white hover:bg-accent/90"
-              data-test-id="provider-settings-done"
-              @click="providerSettings.save"
-            >
-              {{ dialogs.done }}
-            </PopoverClose>
-          </div>
-        </PopoverContent>
-      </PopoverPortal>
-    </PopoverRoot>
-  </TooltipRoot>
+    <PopoverPortal>
+      <PopoverContent
+        side="top"
+        :side-offset="8"
+        align="end"
+        :collision-padding="16"
+        :avoid-collisions="true"
+        :class="cls.content"
+        @interact-outside="onInteractOutside"
+      >
+        <div class="flex flex-col gap-2.5">
+          <h3 class="text-[11px] font-semibold text-surface">{{ dialogs.aiProvider }}</h3>
+          <ProviderSelectField test-id="provider-settings-provider" />
+          <MaxTokensSection />
+          <StockPhotoKeysSection />
+          <CustomEndpointSection />
+          <ApiTypeSection />
+          <ApiKeySection />
+
+          <PopoverClose
+            class="mt-1 w-full rounded bg-accent px-2 py-1 text-center text-[11px] font-medium text-white hover:bg-accent/90"
+            data-test-id="provider-settings-done"
+            @click="providerSettings.save"
+          >
+            {{ dialogs.done }}
+          </PopoverClose>
+        </div>
+      </PopoverContent>
+    </PopoverPortal>
+  </PopoverRoot>
 </template>
diff --git a/src/components/ui/Tip.vue b/src/components/ui/Tip.vue
index c8c7a4f56..6b0cad682 100644
--- a/src/components/ui/Tip.vue
+++ b/src/components/ui/Tip.vue
@@ -1,26 +1,172 @@
 <script setup lang="ts">
-import { TooltipContent, TooltipPortal, TooltipRoot, TooltipTrigger } from 'reka-ui'
+import { useEventListener } from '@vueuse/core'
+import { computed, nextTick, onBeforeUnmount, ref, watch } from 'vue'
 
 import { useTooltipUI } from '@/components/ui/tooltip'
 
+const TOOLTIP_OPEN_DELAY_MS = 400
+const TOOLTIP_SIDE_OFFSET = 4
+const TOOLTIP_VIEWPORT_PADDING = 8
+
+type TooltipSide = 'top' | 'bottom' | 'left' | 'right'
+
 const cls = useTooltipUI({ content: 'animate-in zoom-in-95 fade-in' })
 
-const { side = 'top', disabled = false } = defineProps<{
+const {
+  side = 'top',
+  disabled = false,
+  label
+} = defineProps<{
   label?: string
-  side?: 'top' | 'bottom' | 'left' | 'right'
+  side?: TooltipSide
   disabled?: boolean
 }>()
+
+const triggerRef = ref<HTMLElement>()
+const contentRef = ref<HTMLElement>()
+const open = ref(false)
+const position = ref({ x: 0, y: 0 })
+let openTimer: ReturnType<typeof setTimeout> | undefined
+
+const canOpen = computed(() => Boolean(label) && !disabled)
+const contentStyle = computed(() => ({
+  left: `${position.value.x}px`,
+  top: `${position.value.y}px`
+}))
+
+function clearOpenTimer() {
+  if (!openTimer) return
+  clearTimeout(openTimer)
+  openTimer = undefined
+}
+
+function anchorElement() {
+  const root = triggerRef.value
+  const child = root?.firstElementChild
+  return child instanceof HTMLElement ? child : root
+}
+
+function clamp(value: number, min: number, max: number) {
+  return Math.min(Math.max(value, min), max)
+}
+
+function refreshPosition() {
+  if (!open.value) return
+
+  const anchor = anchorElement()
+  const content = contentRef.value
+  if (!anchor || !content) return
+
+  const anchorRect = anchor.getBoundingClientRect()
+  const contentRect = content.getBoundingClientRect()
+  const centerX = anchorRect.left + anchorRect.width / 2
+  const centerY = anchorRect.top + anchorRect.height / 2
+
+  let x = centerX - contentRect.width / 2
+  let y = anchorRect.top - contentRect.height - TOOLTIP_SIDE_OFFSET
+
+  if (side === 'bottom') y = anchorRect.bottom + TOOLTIP_SIDE_OFFSET
+  if (side === 'left') {
+    x = anchorRect.left - contentRect.width - TOOLTIP_SIDE_OFFSET
+    y = centerY - contentRect.height / 2
+  }
+  if (side === 'right') {
+    x = anchorRect.right + TOOLTIP_SIDE_OFFSET
+    y = centerY - contentRect.height / 2
+  }
+
+  position.value = {
+    x: clamp(
+      x,
+      TOOLTIP_VIEWPORT_PADDING,
+      window.innerWidth - contentRect.width - TOOLTIP_VIEWPORT_PADDING
+    ),
+    y: clamp(
+      y,
+      TOOLTIP_VIEWPORT_PADDING,
+      window.innerHeight - contentRect.height - TOOLTIP_VIEWPORT_PADDING
+    )
+  }
+}
+
+function show() {
+  if (!canOpen.value) return
+  clearOpenTimer()
+  openTimer = setTimeout(() => {
+    open.value = true
+    void nextTick(refreshPosition)
+  }, TOOLTIP_OPEN_DELAY_MS)
+}
+
+function hide() {
+  clearOpenTimer()
+  open.value = false
+}
+
+function containsRelatedTarget(event: PointerEvent | FocusEvent) {
+  const relatedTarget = event.relatedTarget
+  return relatedTarget instanceof Node && triggerRef.value?.contains(relatedTarget)
+}
+
+function onPointerOver(event: PointerEvent) {
+  if (containsRelatedTarget(event)) return
+  show()
+}
+
+function onPointerOut(event: PointerEvent) {
+  if (containsRelatedTarget(event)) return
+  hide()
+}
+
+function onFocusIn(event: FocusEvent) {
+  if (containsRelatedTarget(event)) return
+  show()
+}
+
+function onFocusOut(event: FocusEvent) {
+  if (containsRelatedTarget(event)) return
+  hide()
+}
+
+function onPointerDown() {
+  hide()
+}
+
+useEventListener(window, 'resize', refreshPosition)
+useEventListener(window, 'scroll', refreshPosition, { capture: true, passive: true })
+useEventListener(document, 'pointerdown', hide, { capture: true })
+useEventListener(document, 'click', hide, { capture: true })
+
+watch(canOpen, (value) => {
+  if (!value) hide()
+})
+
+onBeforeUnmount(hide)
 </script>
 
 <template>
-  <TooltipRoot :open="disabled ? false : undefined">
-    <TooltipTrigger as-child>
-      <slot />
-    </TooltipTrigger>
-    <TooltipPortal>
-      <TooltipContent v-if="label" :side="side" :side-offset="4" :class="cls.content">
-        {{ label }}
-      </TooltipContent>
-    </TooltipPortal>
-  </TooltipRoot>
+  <span
+    ref="triggerRef"
+    class="contents"
+    @focusin="onFocusIn"
+    @focusout="onFocusOut"
+    @pointerover="onPointerOver"
+    @pointerout="onPointerOut"
+    @pointerdown="onPointerDown"
+    @click="hide"
+  >
+    <slot />
+  </span>
+  <Teleport to="body">
+    <div
+      v-if="open && label"
+      ref="contentRef"
+      role="tooltip"
+      :class="cls.content"
+      class="pointer-events-none fixed"
+      :style="contentStyle"
+    >
+      {{ label }}
+    </div>
+  </Teleport>
 </template>
diff --git a/tests/e2e/design/panel.spec.ts b/tests/e2e/design/panel.spec.ts
index 6fa7c4167..a11ece676 100644
--- a/tests/e2e/design/panel.spec.ts
+++ b/tests/e2e/design/panel.spec.ts
@@ -1,4 +1,4 @@
-import { expect, test, useEditorSetup } from '#tests/e2e/fixtures'
+import { expect, expectInViewport, test, useEditorSetup } from '#tests/e2e/fixtures'
 import { expectDefined } from '#tests/helpers/assert'
 
 const editor = useEditorSetup()
@@ -305,8 +305,19 @@ test('multi-select shows mixed header and boolean operations', async () => {
   await expect(multiHeader).toContainText('Mixed')
   await expect(multiHeader).toContainText('layers')
 
-  await editor.page.getByTestId('boolean-operations-trigger').click()
-  await expect(editor.page.getByTestId('boolean-operation-booleanUnion')).toBeVisible()
+  const booleanOperations = editor.page.getByTestId('boolean-operations-trigger')
+  await booleanOperations.hover()
+  await expect(
+    editor.page.locator('[role=tooltip]').filter({ hasText: 'Boolean operations' })
+  ).toBeVisible()
+
+  await booleanOperations.click()
+  await expect(
+    editor.page.locator('[role=tooltip]').filter({ hasText: 'Boolean operations' })
+  ).toHaveCount(0)
+  const booleanUnion = editor.page.getByTestId('boolean-operation-booleanUnion')
+  await expect(booleanUnion).toBeVisible()
+  await expectInViewport(editor.page, booleanUnion)
   await expect(editor.page.getByTestId('boolean-operation-booleanSubtract')).toBeVisible()
   await expect(editor.page.getByTestId('boolean-operation-booleanIntersect')).toBeVisible()
   await expect(editor.page.getByTestId('boolean-operation-booleanExclude')).toBeVisible()
diff --git a/tests/e2e/export/basic.spec.ts b/tests/e2e/export/basic.spec.ts
index efcbe0ae4..ad1e7bf8d 100644
--- a/tests/e2e/export/basic.spec.ts
+++ b/tests/e2e/export/basic.spec.ts
@@ -1,5 +1,6 @@
 import { test, expect, type Page } from '@playwright/test'
 
+import { expectInViewport } from '#tests/e2e/fixtures'
 import { CanvasHelper } from '#tests/helpers/canvas'
 
 let page: Page
@@ -50,9 +51,15 @@ test('remove export row decreases row count', async () => {
 
 test('format selector changes to JPG', async () => {
   const formatTrigger = exportItems().first().getByTestId('app-select-trigger').last()
+  await formatTrigger.hover()
+  await expect(page.locator('[role=tooltip]').filter({ hasText: 'Export format' })).toBeVisible()
   await formatTrigger.click()
+  await expect(page.locator('[role=tooltip]').filter({ hasText: 'Export format' })).toHaveCount(0)
 
-  await page.locator('[role="option"]').filter({ hasText: 'JPG' }).click()
+  const jpgOption = page.locator('[role="option"]').filter({ hasText: 'JPG' })
+  await expect(jpgOption).toBeVisible()
+  await expectInViewport(page, jpgOption)
+  await jpgOption.click()
   await canvas.waitForRender()
 
   await expect(formatTrigger).toHaveText('JPG')
diff --git a/tests/e2e/fixtures.ts b/tests/e2e/fixtures.ts
index bb851f358..8e84e84e0 100644
--- a/tests/e2e/fixtures.ts
+++ b/tests/e2e/fixtures.ts
@@ -1,4 +1,4 @@
-import { test, expect, type Page } from '@playwright/test'
+import { test, expect, type Locator, type Page } from '@playwright/test'
 
 import { CanvasHelper } from '#tests/helpers/canvas'
 
@@ -39,4 +39,17 @@ export function useEditorSetupWithClear(url = '/') {
   return ctx
 }
 
+export async function expectInViewport(page: Page, locator: Locator) {
+  const box = await locator.boundingBox()
+  if (!box) throw new Error('Expected visible element to have a bounding box')
+
+  const viewport = page.viewportSize()
+  if (!viewport) throw new Error('Expected page to have a viewport')
+
+  expect(box.x).toBeGreaterThanOrEqual(0)
+  expect(box.y).toBeGreaterThanOrEqual(0)
+  expect(box.x + box.width).toBeLessThanOrEqual(viewport.width)
+  expect(box.y + box.height).toBeLessThanOrEqual(viewport.height)
+}
+
 export { test, expect }
diff --git a/tests/e2e/fonts/settings.spec.ts b/tests/e2e/fonts/settings.spec.ts
index 7aef538f8..14fe6b0a5 100644
--- a/tests/e2e/fonts/settings.spec.ts
+++ b/tests/e2e/fonts/settings.spec.ts
@@ -18,7 +18,11 @@ test('font settings popover exposes web font access without desktop-only cache a
   })
 
   await expect(page.getByTestId('typography-section')).toBeVisible()
-  await page.getByTestId('font-settings-trigger').click()
+  const fontSettings = page.getByTestId('font-settings-trigger')
+  await fontSettings.hover()
+  await expect(page.locator('[role=tooltip]').filter({ hasText: 'Font settings' })).toBeVisible()
+  await fontSettings.click()
+  await expect(page.locator('[role=tooltip]').filter({ hasText: 'Font settings' })).toHaveCount(0)
 
   await expect(page.getByText('Allow browser access to local fonts')).toBeVisible()
   await expect(page.getByTestId('font-settings-request-access')).toBeVisible()