diff --git a/services/web/frontend/js/features/source-editor/extensions/index.ts b/services/web/frontend/js/features/source-editor/extensions/index.ts
index e3c0a28ccb..f7ab774d15 100644
--- a/services/web/frontend/js/features/source-editor/extensions/index.ts
+++ b/services/web/frontend/js/features/source-editor/extensions/index.ts
@@ -53,6 +53,7 @@ import { ranges } from './ranges'
 import { historyOT } from './history-ot'
 import { trackDetachedComments } from './track-detached-comments'
 import { reviewTooltip } from './review-tooltip'
+import { tooltipsReposition } from './tooltips-reposition'
 
 const moduleExtensions: Array<(options: Record<string, any>) => Extension> =
   importOverleafModules('sourceEditorExtensions').map(
@@ -170,4 +171,5 @@ export const createExtensions = (options: Record<string, any>): Extension[] => [
   effectListeners(),
   geometryChangeEvent(),
   fileTreeItemDrop(),
+  tooltipsReposition(),
 ]
diff --git a/services/web/frontend/js/features/source-editor/extensions/math-preview.ts b/services/web/frontend/js/features/source-editor/extensions/math-preview.ts
index 3df55b2f28..1b9e051978 100644
--- a/services/web/frontend/js/features/source-editor/extensions/math-preview.ts
+++ b/services/web/frontend/js/features/source-editor/extensions/math-preview.ts
@@ -1,10 +1,4 @@
-import {
-  EditorView,
-  repositionTooltips,
-  showTooltip,
-  Tooltip,
-  ViewPlugin,
-} from '@codemirror/view'
+import { EditorView, showTooltip, Tooltip, ViewPlugin } from '@codemirror/view'
 import {
   Compartment,
   EditorState,
@@ -24,8 +18,8 @@ import { documentCommands } from '../languages/latex/document-commands'
 import { debugConsole } from '@/utils/debugging'
 import { nodeHasError } from '../utils/tree-operations/common'
 import { documentEnvironments } from '../languages/latex/document-environments'
+import { repositionAllTooltips } from './tooltips-reposition'
 
-const REPOSITION_EVENT = 'editor:repositionMathTooltips'
 const HIDE_TOOLTIP_EVENT = 'editor:hideMathTooltip'
 
 export const mathPreview = (enabled: boolean): Extension => {
@@ -81,19 +75,16 @@ export const mathPreviewStateField = StateField.define<{
     showTooltip.compute([field], state => state.field(field).tooltip),
 
     ViewPlugin.define(view => {
-      const listener = () => repositionTooltips(view)
       const hideTooltip = () => {
         view.dispatch({
           effects: hideTooltipEffect.of(null),
         })
       }
 
-      window.addEventListener(REPOSITION_EVENT, listener)
       window.addEventListener(HIDE_TOOLTIP_EVENT, hideTooltip)
 
       return {
         destroy() {
-          window.removeEventListener(REPOSITION_EVENT, listener)
           window.removeEventListener(HIDE_TOOLTIP_EVENT, hideTooltip)
         },
       }
@@ -220,7 +211,7 @@ const buildTooltipContent = (
   renderMath(math.content, math.displayMode, element, definitions)
     .then(() => {
       element.style.opacity = '1'
-      window.dispatchEvent(new Event(REPOSITION_EVENT))
+      repositionAllTooltips()
     })
     .catch(error => {
       debugConsole.error(error)
diff --git a/services/web/frontend/js/features/source-editor/extensions/tooltips-reposition.ts b/services/web/frontend/js/features/source-editor/extensions/tooltips-reposition.ts
new file mode 100644
index 0000000000..cb350b2e06
--- /dev/null
+++ b/services/web/frontend/js/features/source-editor/extensions/tooltips-reposition.ts
@@ -0,0 +1,20 @@
+import { repositionTooltips, ViewPlugin } from '@codemirror/view'
+
+const REPOSITION_EVENT = 'editor:repositionAllTooltips'
+
+export const tooltipsReposition = () =>
+  ViewPlugin.define(view => {
+    const listener = () => repositionTooltips(view)
+
+    window.addEventListener(REPOSITION_EVENT, listener)
+
+    return {
+      destroy() {
+        window.removeEventListener(REPOSITION_EVENT, listener)
+      },
+    }
+  })
+
+export const repositionAllTooltips = () => {
+  window.dispatchEvent(new Event(REPOSITION_EVENT))
+}
diff --git a/services/web/frontend/js/shared/context/layout-context.tsx b/services/web/frontend/js/shared/context/layout-context.tsx
index 8dcc1fd8ff..6bc8c5b222 100644
--- a/services/web/frontend/js/shared/context/layout-context.tsx
+++ b/services/web/frontend/js/shared/context/layout-context.tsx
@@ -21,6 +21,7 @@ import { isMac } from '@/shared/utils/os'
 import { sendSearchEvent } from '@/features/event-tracking/search-events'
 import { useRailContext } from '@/features/ide-redesign/contexts/rail-context'
 import usePersistedState from '@/shared/hooks/use-persisted-state'
+import { repositionAllTooltips } from '@/features/source-editor/extensions/tooltips-reposition'
 
 export type IdeLayout = 'sideBySide' | 'flat'
 export type IdeView = 'editor' | 'file' | 'pdf' | 'history'
@@ -198,6 +199,15 @@ export const LayoutProvider: FC<React.PropsWithChildren> = ({ children }) => {
     [setPdfLayout, setView]
   )
 
+  // Force codemirror to reposition all tooltips to prevent an issue
+  // where tooltips would sometimes show on top of the pdf preview
+  // https://github.com/overleaf/internal/issues/23840
+  useEffect(() => {
+    if (view === 'pdf' && pdfLayout === 'flat') {
+      repositionAllTooltips()
+    }
+  }, [view, pdfLayout])
+
   const {
     reattach,
     detach,