diff --git a/packages/core/src/components/Dialog/Dialog.tsx b/packages/core/src/components/Dialog/Dialog.tsx
index 47b3e92ee8..e91248dde2 100644
--- a/packages/core/src/components/Dialog/Dialog.tsx
+++ b/packages/core/src/components/Dialog/Dialog.tsx
@@ -19,6 +19,7 @@ import { ComponentDefaultTestId, getTestId } from "../../tests/test-ids-utils";
 import { DialogAnimationType, DialogPosition, DialogTriggerEvent } from "./Dialog.types";
 import LayerContext from "../LayerProvider/LayerContext";
 import { isClient } from "../../utils/ssr-utils";
+import { createObserveContentResizeModifier } from "./modifiers/observeContentResizeModifier";
 
 export interface DialogProps extends VibeComponentProps {
   /**
@@ -584,22 +585,7 @@ export default class Dialog extends PureComponent<DialogProps, DialogState> {
                     return state;
                   }
                 },
-                {
-                  name: "observeContentResize",
-                  enabled: observeContentResize,
-                  phase: "beforeWrite",
-                  fn() {},
-                  effect({ state, instance }) {
-                    const observer = new ResizeObserver(() => {
-                      instance.update();
-                    });
-                    observer.observe(state.elements.popper);
-
-                    return () => {
-                      observer.disconnect();
-                    };
-                  }
-                },
+                createObserveContentResizeModifier(observeContentResize),
                 ...modifiers
               ]}
             >
diff --git a/packages/core/src/components/Dialog/modifiers/observeContentResizeModifier.ts b/packages/core/src/components/Dialog/modifiers/observeContentResizeModifier.ts
new file mode 100644
index 0000000000..e6d90ff5be
--- /dev/null
+++ b/packages/core/src/components/Dialog/modifiers/observeContentResizeModifier.ts
@@ -0,0 +1,18 @@
+import { Modifier } from "react-popper";
+
+export const createObserveContentResizeModifier = (isEnabled = false): Modifier<"observeContentResize"> => ({
+  name: "observeContentResize",
+  enabled: isEnabled,
+  phase: "beforeWrite",
+  fn() {},
+  effect({ state, instance }) {
+    const observer = new ResizeObserver(() => {
+      instance.update();
+    });
+    observer.observe(state.elements.popper);
+
+    return () => {
+      observer.disconnect();
+    };
+  }
+});
diff --git a/packages/core/src/components/Menu/MenuItem/MenuItem.tsx b/packages/core/src/components/Menu/MenuItem/MenuItem.tsx
index 7fdc05cc7f..280cfd1520 100644
--- a/packages/core/src/components/Menu/MenuItem/MenuItem.tsx
+++ b/packages/core/src/components/Menu/MenuItem/MenuItem.tsx
@@ -56,6 +56,12 @@ export interface MenuItemProps extends VibeComponentProps {
   splitMenuItem?: boolean;
   "aria-label"?: AriaAttributes["aria-label"];
   submenuPosition?: SubmenuPosition;
+  /**
+   * When set to `true`, submenu's content and size changes would automatically trigger repositioning.
+   *
+   * This is useful for when submenu's content may grow or shrink without a re-render being triggered.
+   */
+  autoAdjustOnSubMenuContentResize?: boolean;
 }
 
 export interface MenuItemTitleComponentProps extends Omit<MenuItemProps, "title"> {
diff --git a/packages/core/src/components/Menu/MenuItem/components/BaseMenuItem/BaseMenuItem.tsx b/packages/core/src/components/Menu/MenuItem/components/BaseMenuItem/BaseMenuItem.tsx
index 9949310da3..ef9703b27d 100644
--- a/packages/core/src/components/Menu/MenuItem/components/BaseMenuItem/BaseMenuItem.tsx
+++ b/packages/core/src/components/Menu/MenuItem/components/BaseMenuItem/BaseMenuItem.tsx
@@ -39,7 +39,8 @@ const BaseMenuItem = forwardRef(
       "data-testid": dataTestId,
       splitMenuItem = false,
       children,
-      submenuPosition = "right"
+      submenuPosition = "right",
+      autoAdjustOnSubMenuContentResize
     }: BaseMenuItemProps,
     ref: React.ForwardedRef<HTMLElement>
   ) => {
@@ -153,6 +154,7 @@ const BaseMenuItem = forwardRef(
               onClose={closeSubMenu}
               autoFocusOnMount={!useDocumentEventListeners}
               submenuPosition={submenuPosition}
+              autoAdjustOnSubMenuContentResize={autoAdjustOnSubMenuContentResize}
             >
               {subMenu}
             </MenuItemSubMenu>
diff --git a/packages/core/src/components/Menu/MenuItem/components/MenuItemSubMenu/MenuItemSubMenu.tsx b/packages/core/src/components/Menu/MenuItem/components/MenuItemSubMenu/MenuItemSubMenu.tsx
index abfd1859ce..a58fae2fb5 100644
--- a/packages/core/src/components/Menu/MenuItem/components/MenuItemSubMenu/MenuItemSubMenu.tsx
+++ b/packages/core/src/components/Menu/MenuItem/components/MenuItemSubMenu/MenuItemSubMenu.tsx
@@ -12,7 +12,8 @@ const MenuItemSubMenu = ({
   autoFocusOnMount,
   onClose,
   children,
-  submenuPosition
+  submenuPosition,
+  autoAdjustOnSubMenuContentResize
 }: MenuItemSubMenuProps) => {
   const childRef = useRef<HTMLDivElement>(null);
   const popperElementRef = useRef<HTMLDivElement>(null);
@@ -36,7 +37,8 @@ const MenuItemSubMenu = ({
     popperElementRef?.current,
     {
       isOpen: open,
-      placement: submenuPlacement
+      placement: submenuPlacement,
+      observeContentResize: autoAdjustOnSubMenuContentResize
     }
   );
 
diff --git a/packages/core/src/components/Menu/MenuItem/components/MenuItemSubMenu/MenuItemSubMenu.types.ts b/packages/core/src/components/Menu/MenuItem/components/MenuItemSubMenu/MenuItemSubMenu.types.ts
index 8eac7274de..7c6cc29ad7 100644
--- a/packages/core/src/components/Menu/MenuItem/components/MenuItemSubMenu/MenuItemSubMenu.types.ts
+++ b/packages/core/src/components/Menu/MenuItem/components/MenuItemSubMenu/MenuItemSubMenu.types.ts
@@ -1,8 +1,9 @@
 import React from "react";
 import { CloseMenuOption, MenuChild } from "../../../Menu/MenuConstants";
 import { SubmenuPosition } from "../../MenuItem.types";
+import { MenuItemProps } from "../../MenuItem";
 
-export interface MenuItemSubMenuProps {
+export interface MenuItemSubMenuProps extends Pick<MenuItemProps, "autoAdjustOnSubMenuContentResize"> {
   /**
    * Reference to the anchor element that the submenu is related to. This is used to position the submenu correctly relative to the parent menu item.
    */
diff --git a/packages/core/src/hooks/usePopover.ts b/packages/core/src/hooks/usePopover.ts
index 6cf3159f50..10e36606c6 100644
--- a/packages/core/src/hooks/usePopover.ts
+++ b/packages/core/src/hooks/usePopover.ts
@@ -4,6 +4,7 @@ import { Placement } from "./popoverConstants";
 import useIsomorphicLayoutEffect from "./ssr/useIsomorphicLayoutEffect";
 import useForceUpdate from "./useForceUpdate";
 import type { Options, State } from "@popperjs/core";
+import { createObserveContentResizeModifier } from "../components/Dialog/modifiers/observeContentResizeModifier";
 
 const { RIGHT_START, RIGHT_END, LEFT_START, LEFT_END } = Placement;
 
@@ -19,10 +20,12 @@ export default function usePopover(
   popperElement: HTMLElement,
   {
     isOpen,
-    placement = RIGHT_START
+    placement = RIGHT_START,
+    observeContentResize
   }: {
     isOpen?: boolean;
     placement?: Placement;
+    observeContentResize?: boolean;
   }
 ) {
   const forceUpdate = useForceUpdate();
@@ -46,10 +49,11 @@ export default function usePopover(
             state.styles.popper.visibility = isOpen ? "visible" : "hidden";
             return state;
           }
-        }
+        },
+        createObserveContentResizeModifier(observeContentResize)
       ]
     };
-  }, [isOpen, placement]);
+  }, [isOpen, placement, observeContentResize]);
 
   const { styles, attributes } = usePopper(referenceElement, popperElement, popperOptions);