diff --git a/packages/app/src/components/layout/AppLayout.tsx b/packages/app/src/components/layout/AppLayout.tsx
index e995265a7..f2c8e6da9 100644
--- a/packages/app/src/components/layout/AppLayout.tsx
+++ b/packages/app/src/components/layout/AppLayout.tsx
@@ -150,6 +150,15 @@ export function AppLayout() {
     return () => window.removeEventListener("keydown", handleKeyDown, { capture: true });
   }, [toggleCommandPalette]);
 
+  useEffect(() => {
+    const handleContextMenu = (event: MouseEvent) => {
+      event.preventDefault();
+    };
+
+    window.addEventListener("contextmenu", handleContextMenu, { capture: true });
+    return () => window.removeEventListener("contextmenu", handleContextMenu, { capture: true });
+  }, []);
+
   useEffect(() => {
     if (!isReaderActive) return;
 
diff --git a/packages/app/src/components/reader/ReaderView.tsx b/packages/app/src/components/reader/ReaderView.tsx
index 754f7cee5..74ab474db 100644
--- a/packages/app/src/components/reader/ReaderView.tsx
+++ b/packages/app/src/components/reader/ReaderView.tsx
@@ -2833,6 +2833,7 @@ export function ReaderView({ bookId, tabId }: ReaderViewProps) {
               <SelectionPopover
                 position={selectionPos}
                 selectedText={selection.text}
+                selectionRects={selection.rects}
                 annotated={selection.annotated}
                 currentColor={selection.color as HighlightColor | undefined}
                 defaultColor={viewSettings.defaultHighlightColor ?? "yellow"}
diff --git a/packages/app/src/components/reader/SelectionPopover.tsx b/packages/app/src/components/reader/SelectionPopover.tsx
index 34d3d48de..1e9f5c5fe 100644
--- a/packages/app/src/components/reader/SelectionPopover.tsx
+++ b/packages/app/src/components/reader/SelectionPopover.tsx
@@ -20,6 +20,7 @@ import { useTranslation } from "react-i18next";
 interface SelectionPopoverProps {
   position: { x: number; y: number };
   selectedText: string;
+  selectionRects: DOMRect[];
   annotated?: boolean; // true if this is an existing annotation
   currentColor?: HighlightColor; // current highlight color (for existing annotations)
   defaultColor?: HighlightColor;
@@ -39,6 +40,7 @@ const POPOVER_MARGIN = 8;
 export function SelectionPopover({
   position,
   selectedText: _selectedText,
+  selectionRects,
   annotated = false,
   currentColor,
   defaultColor = "yellow",
@@ -57,8 +59,33 @@ export function SelectionPopover({
   const [selectedColor, setSelectedColor] = useState<HighlightColor>(currentColor || defaultColor);
   const overlayRef = useRef<HTMLDivElement>(null);
   const popoverRef = useRef<HTMLDivElement>(null);
+  const closeTimerRef = useRef<ReturnType<typeof setTimeout> | null>(null);
   const [clampedPosition, setClampedPosition] = useState(position);
 
+  const clearPendingClose = () => {
+    if (!closeTimerRef.current) return;
+    clearTimeout(closeTimerRef.current);
+    closeTimerRef.current = null;
+  };
+
+  const selectionBounds = selectionRects.reduce<DOMRect | null>((bounds, rect) => {
+    if (!bounds) {
+      return new DOMRect(rect.left, rect.top, rect.width, rect.height);
+    }
+    const left = Math.min(bounds.left, rect.left);
+    const top = Math.min(bounds.top, rect.top);
+    const right = Math.max(bounds.right, rect.right);
+    const bottom = Math.max(bounds.bottom, rect.bottom);
+    return new DOMRect(left, top, right - left, bottom - top);
+  }, null);
+
+  const isPointInsideSelection = (x: number, y: number) =>
+    !!selectionBounds &&
+    x >= selectionBounds.left &&
+    x <= selectionBounds.right &&
+    y >= selectionBounds.top &&
+    y <= selectionBounds.bottom;
+
   const handleHighlightClick = () => {
     // PDF doesn't support highlighting
     if (isPdf) return;
@@ -121,13 +148,31 @@ export function SelectionPopover({
     );
   });
 
+  const handleBackdropClick = () => {
+    clearPendingClose();
+    closeTimerRef.current = setTimeout(() => {
+      closeTimerRef.current = null;
+      onClose();
+    }, 320);
+  };
+
+  const handleBackdropDoubleClick = (event: React.MouseEvent<HTMLButtonElement>) => {
+    clearPendingClose();
+    if (!isPointInsideSelection(event.clientX, event.clientY)) {
+      onClose();
+      return;
+    }
+    onAskAI();
+  };
+
   return (
     <div ref={overlayRef} className="absolute inset-0 z-50">
       <button
         type="button"
         aria-label={t("common.close")}
         className="absolute inset-0 cursor-default"
-        onClick={onClose}
+        onClick={handleBackdropClick}
+        onDoubleClick={handleBackdropDoubleClick}
       />
       <div
         ref={popoverRef}
diff --git a/packages/app/src/lib/reader/iframe-event-handlers.ts b/packages/app/src/lib/reader/iframe-event-handlers.ts
index 2d4352021..96045ca01 100644
--- a/packages/app/src/lib/reader/iframe-event-handlers.ts
+++ b/packages/app/src/lib/reader/iframe-event-handlers.ts
@@ -142,6 +142,10 @@ export const handleMouseup = (bookKey: string, event: MouseEvent) => {
   );
 };
 
+export const handleContextMenu = (event: MouseEvent) => {
+  event.preventDefault();
+};
+
 /** Single-click detection with double-click exclusion */
 let clickTimer: ReturnType<typeof setTimeout> | null = null;
 let clickCount = 0;
@@ -231,6 +235,7 @@ export function registerIframeEventHandlers(bookKey: string, doc: Document): voi
   doc.addEventListener("keyup", handleKeyup.bind(null, bookKey));
   doc.addEventListener("mousedown", handleMousedown.bind(null, bookKey));
   doc.addEventListener("mouseup", handleMouseup.bind(null, bookKey));
+  doc.addEventListener("contextmenu", handleContextMenu, { capture: true });
   doc.addEventListener("click", handleClick.bind(null, bookKey));
   doc.addEventListener("wheel", handleWheel.bind(null, bookKey), {
     passive: true,