diff --git a/components/ui/__tests__/context-menu-placement.test.tsx b/components/ui/__tests__/context-menu-placement.test.tsx
index a856a4268..d1345b377 100644
--- a/components/ui/__tests__/context-menu-placement.test.tsx
+++ b/components/ui/__tests__/context-menu-placement.test.tsx
@@ -98,6 +98,25 @@ describe('a menu from a button', () => {
     expect(openAt({ x: 0, y: 0, anchor: { left: 100, top: 600, right: 132, bottom: 632 } }).top).toBe(600 - 4 - MENU.height);
   });
 
+  it('too tall for either side: stays under the button, as tall as the room, and scrolls', () => {
+    // The ⋮ menu at 150 % zoom: 480 CSS pixels of window.
+    Object.defineProperty(window, 'innerHeight', { value: 480, configurable: true });
+    MENU.height = 460;
+    try {
+      render(
+        <ContextMenu isOpen position={{ x: 0, y: 0, anchor: { left: 805, top: 12, right: 837, bottom: 44, align: 'end' } }} onClose={() => {}}>
+          <ContextMenuItem label="Reply" onClick={() => {}} />
+        </ContextMenu>,
+      );
+      const menu = screen.getByRole('menu');
+      // Clamped instead, it sat at 10 and covered its own button.
+      expect(menu.style.top).toBe('48px');
+      expect((menu.firstElementChild as HTMLElement).style.maxHeight).toBe(`${480 - 10 - 48 - 2}px`);
+    } finally {
+      MENU.height = 300;
+    }
+  });
+
   it('mirrors in RTL: start is the right edge', () => {
     document.documentElement.dir = 'rtl';
     const at = openAt({ x: 0, y: 0, anchor: { left: 500, top: 40, right: 532, bottom: 72 } });
diff --git a/components/ui/context-menu.tsx b/components/ui/context-menu.tsx
index 84e0c359c..0498a3dc3 100644
--- a/components/ui/context-menu.tsx
+++ b/components/ui/context-menu.tsx
@@ -242,7 +242,7 @@ function useMenuLevel(recentTouch: () => boolean): MenuLevel {
 export const ContextMenu = forwardRef<HTMLDivElement, ContextMenuProps>(
   ({ isOpen, position, onClose, children, label }, ref) => {
     const [mounted, setMounted] = useState(false);
-    const [adjustedPosition, setAdjustedPosition] = useState<Position | null>(null);
+    const [adjustedPosition, setAdjustedPosition] = useState<(Position & { maxHeight?: number }) | null>(null);
     const localRef = useRef<HTMLDivElement | null>(null);
     const onCloseRef = useRef(onClose);
     useEffect(() => {
@@ -326,18 +326,25 @@ export const ContextMenu = forwardRef<HTMLDivElement, ContextMenuProps>(
 
       const clamp = () => {
         const rect = node.getBoundingClientRect();
+        // The height it would have uncapped: a cap set last time mustn't decide the next.
+        const list = node.firstElementChild as HTMLElement | null;
+        const height = list && list.scrollHeight > list.clientHeight
+          ? rect.height + list.scrollHeight - list.clientHeight
+          : rect.height;
         // Next to the button it opened from, or at the pointer (lib/menu-placement.ts).
-        const { x, y } = placeMenu({
+        const { x, y, maxHeight } = placeMenu({
           point: { x: position.x, y: position.y },
           anchor,
-          size: { width: rect.width, height: rect.height },
+          size: { width: rect.width, height },
           viewport: { width: window.innerWidth, height: window.innerHeight },
           rtl: getComputedStyle(node).direction === "rtl",
           margin: VIEWPORT_MARGIN,
           gap: ANCHOR_GAP,
         });
 
-        setAdjustedPosition((prev) => (prev && prev.x === x && prev.y === y ? prev : { x, y }));
+        setAdjustedPosition((prev) =>
+          prev && prev.x === x && prev.y === y && prev.maxHeight === maxHeight ? prev : { x, y, maxHeight }
+        );
       };
       clamp();
       if (typeof ResizeObserver === "undefined") return;
@@ -528,7 +535,14 @@ export const ContextMenu = forwardRef<HTMLDivElement, ContextMenuProps>(
           }}
         >
           {/* Taller than the window: scroll inside the menu. */}
-          <div className="py-1 overflow-y-auto" style={{ maxHeight: `calc(100vh - ${2 * VIEWPORT_MARGIN + 2}px)` }}>
+          <div
+            className="py-1 overflow-y-auto"
+            style={{
+              maxHeight: adjustedPosition?.maxHeight !== undefined
+                ? `${Math.max(0, adjustedPosition.maxHeight - 2)}px`
+                : `calc(100vh - ${2 * VIEWPORT_MARGIN + 2}px)`,
+            }}
+          >
             {children}
           </div>
         </div>
diff --git a/lib/menu-placement.ts b/lib/menu-placement.ts
index a8397d1ee..146c6b391 100644
--- a/lib/menu-placement.ts
+++ b/lib/menu-placement.ts
@@ -50,8 +50,9 @@ export function placeMenu({
   rtl = false,
   margin = MENU_VIEWPORT_MARGIN,
   gap = MENU_ANCHOR_GAP,
-}: MenuPlacementInput): { x: number; y: number } {
-  const { width: w, height: h } = size;
+}: MenuPlacementInput): { x: number; y: number; maxHeight?: number } {
+  const { width: w } = size;
+  let h = size.height;
   const { width: vw, height: vh } = viewport;
   const fitsX = (x: number) => x >= margin && x + w <= vw - margin;
   const fitsY = (y: number) => y >= margin && y + h <= vh - margin;
@@ -69,8 +70,16 @@ export function placeMenu({
     const above = anchor.top - gap - h;
     if (fitsY(below)) y = below;
     else if (fitsY(above)) y = above;
-    // Neither fits whole: the side with more room, and the menu scrolls.
-    else y = vh - anchor.bottom >= anchor.top ? below : above;
+    else {
+      // Neither fits whole: the side with more room, as tall as that room, and
+      // the menu scrolls. Clamped instead, it would cover its own button.
+      const roomBelow = vh - margin - below;
+      const roomAbove = anchor.top - gap - margin;
+      const maxHeight = Math.max(roomBelow, roomAbove);
+      h = Math.min(h, maxHeight);
+      y = roomBelow >= roomAbove ? below : anchor.top - gap - h;
+      return { x: clamp(x, w, vw, margin), y: Math.max(margin, y), maxHeight };
+    }
   } else {
     const towardEnd = rtl ? point.x - w : point.x;
     const towardStart = rtl ? point.x : point.x - w;