diff --git a/frontend/playwright/ui/specs/profile-menu.spec.js b/frontend/playwright/ui/specs/profile-menu.spec.js
index 71bdbb4199..3c12fbb151 100644
--- a/frontend/playwright/ui/specs/profile-menu.spec.js
+++ b/frontend/playwright/ui/specs/profile-menu.spec.js
@@ -28,6 +28,92 @@ test("Navigate to penpot changelog from profile menu", async ({ page }) => {
   );
 });
 
+test("Submenu closes when hovering a menu option without submenu", async ({
+  page,
+}) => {
+  const dashboardPage = new DashboardPage(page);
+  await dashboardPage.goToDashboard();
+
+  await dashboardPage.openProfileMenu();
+  await page.getByText("About Penpot").hover();
+
+  const changelogSubmenuItem = page.getByText("Penpot Changelog");
+  await expect(changelogSubmenuItem).toBeVisible();
+
+  await dashboardPage.userProfileOption.hover();
+  await expect(changelogSubmenuItem).toBeHidden();
+});
+
+test("Submenu stays open while moving the pointer into it", async ({
+  page,
+}) => {
+  const dashboardPage = new DashboardPage(page);
+  await dashboardPage.goToDashboard();
+
+  await dashboardPage.openProfileMenu();
+  const aboutPenpotItem = page.getByText("About Penpot");
+  await aboutPenpotItem.hover();
+
+  const changelogSubmenuItem = page.getByText("Penpot Changelog");
+  await expect(changelogSubmenuItem).toBeVisible();
+
+  // Walk the pointer from the parent option into the submenu the way a
+  // real user does — gradually, crossing the gap between the two menus.
+  const from = await aboutPenpotItem.boundingBox();
+  const to = await changelogSubmenuItem.boundingBox();
+  await page.mouse.move(from.x + from.width / 2, from.y + from.height / 2);
+  await page.mouse.move(to.x + to.width / 2, to.y + to.height / 2, {
+    steps: 20,
+  });
+
+  await expect(changelogSubmenuItem).toBeVisible();
+});
+
+test("Submenu closes when the pointer leaves the menu entirely", async ({
+  page,
+}) => {
+  const dashboardPage = new DashboardPage(page);
+  await dashboardPage.goToDashboard();
+
+  await dashboardPage.openProfileMenu();
+  await page.getByText("About Penpot").hover();
+
+  const changelogSubmenuItem = page.getByText("Penpot Changelog");
+  await expect(changelogSubmenuItem).toBeVisible();
+
+  await dashboardPage.mainHeading.hover();
+  await expect(changelogSubmenuItem).toBeHidden();
+});
+
+test("Hovering another expandable option switches submenus", async ({
+  page,
+}) => {
+  const dashboardPage = new DashboardPage(page);
+  await dashboardPage.goToDashboard();
+
+  await dashboardPage.openProfileMenu();
+  await page.getByText("Help & Learning").hover();
+
+  const helpCenterSubmenuItem = page.getByText("Help Center");
+  await expect(helpCenterSubmenuItem).toBeVisible();
+
+  await page.getByText("About Penpot").hover();
+  await expect(page.getByText("Penpot Changelog")).toBeVisible();
+  await expect(helpCenterSubmenuItem).toBeHidden();
+});
+
+test("Submenu opens with keyboard navigation", async ({ page }) => {
+  const dashboardPage = new DashboardPage(page);
+  await dashboardPage.goToDashboard();
+
+  await dashboardPage.openProfileMenu();
+  await dashboardPage.sidebarMenu
+    .getByRole("menuitem", { name: "Help & Learning" })
+    .press("Enter");
+
+  await expect(page.getByText("Help Center")).toBeVisible();
+});
+
 test("Opens release notes from current version from profile menu", async ({
   page,
 }) => {
diff --git a/frontend/src/app/main/ui/components/dropdown_menu.cljs b/frontend/src/app/main/ui/components/dropdown_menu.cljs
index aad1e9a47e..681682fdae 100644
--- a/frontend/src/app/main/ui/components/dropdown_menu.cljs
+++ b/frontend/src/app/main/ui/components/dropdown_menu.cljs
@@ -27,7 +27,7 @@
 
 (mf/defc internal-dropdown-menu*
   {::mf/private true}
-  [{:keys [on-close children class id]}]
+  [{:keys [on-close children class id on-pointer-enter on-pointer-leave]}]
 
   (assert (fn? on-close) "missing `on-close` prop")
 
@@ -106,7 +106,12 @@
         #(doseq [key keys]
            (events/unlistenByKey key))))
 
-    [:ul {:class class :role "menu" :ref container} children]))
+    [:ul {:class class
+          :role "menu"
+          :ref container
+          :on-pointer-enter on-pointer-enter
+          :on-pointer-leave on-pointer-leave}
+     children]))
 
 (mf/defc dropdown-menu*
   [{:keys [show] :as props}]
diff --git a/frontend/src/app/main/ui/dashboard/sidebar.cljs b/frontend/src/app/main/ui/dashboard/sidebar.cljs
index 420383aa60..bea1060183 100644
--- a/frontend/src/app/main/ui/dashboard/sidebar.cljs
+++ b/frontend/src/app/main/ui/dashboard/sidebar.cljs
@@ -1133,7 +1133,7 @@
 
 (mf/defc help-learning-menu*
   {::mf/private true}
-  [{:keys [on-close on-click]}]
+  [{:keys [on-close on-click on-pointer-enter on-pointer-leave]}]
   (let [handle-click-url
         (mf/use-fn
          (fn [event]
@@ -1150,7 +1150,9 @@
 
     [:> dropdown-menu* {:show true
                         :class (stl/css :sub-menu :help-learning)
-                        :on-close on-close}
+                        :on-close on-close
+                        :on-pointer-enter on-pointer-enter
+                        :on-pointer-leave on-pointer-leave}
 
      [:> dropdown-menu-item* {:class (stl/css :submenu-item)
                               :data-url "https://help.penpot.app"
@@ -1177,7 +1179,7 @@
 
 (mf/defc community-contributions-menu*
   {::mf/private true}
-  [{:keys [on-close]}]
+  [{:keys [on-close on-pointer-enter on-pointer-leave]}]
   (let [handle-click-url
         (mf/use-fn
          (fn [event]
@@ -1191,7 +1193,9 @@
 
     [:> dropdown-menu* {:show true
                         :class (stl/css :sub-menu :community)
-                        :on-close on-close}
+                        :on-close on-close
+                        :on-pointer-enter on-pointer-enter
+                        :on-pointer-leave on-pointer-leave}
 
      [:> dropdown-menu-item* {:class (stl/css :submenu-item)
                               :data-url "https://github.com/penpot/penpot"
@@ -1207,7 +1211,7 @@
 
 (mf/defc about-penpot-menu*
   {::mf/private true}
-  [{:keys [on-close]}]
+  [{:keys [on-close on-pointer-enter on-pointer-leave]}]
   (let [version cf/version
         show-release-notes
         (mf/use-fn
@@ -1230,7 +1234,9 @@
 
     [:> dropdown-menu* {:show true
                         :class (stl/css :sub-menu :about)
-                        :on-close on-close}
+                        :on-close on-close
+                        :on-pointer-enter on-pointer-enter
+                        :on-pointer-leave on-pointer-leave}
 
      [:> dropdown-menu-item* {:class (stl/css :submenu-item)
                               :on-click show-release-notes}
@@ -1255,6 +1261,11 @@
         show-profile-menu? (deref show-profile-menu*)
         sub-menu*      (mf/use-state false)
         sub-menu       (deref sub-menu*)
+
+        ;; Tracks whether the pointer is over an expandable option or
+        ;; its floating submenu, so the submenu survives the gap
+        ;; between them while the pointer travels across.
+        hovering?*     (mf/use-ref false)
         version        (:base cf/version)
 
         close-sub-menu
@@ -1320,6 +1331,24 @@
                           (keyword))]
              (reset! sub-menu* menu))))
 
+        on-menu-pointer-enter
+        (mf/use-fn
+         (fn [event]
+           (mf/set-ref-val! hovering?* true)
+           (on-menu-click event)))
+
+        on-menu-pointer-leave
+        (mf/use-fn
+         (fn [_]
+           (mf/set-ref-val! hovering?* false)
+           (ts/schedule 200 #(when-not (mf/ref-val hovering?*)
+                               (reset! sub-menu* nil)))))
+
+        on-sub-menu-pointer-enter
+        (mf/use-fn
+         (fn [_]
+           (mf/set-ref-val! hovering?* true)))
+
         on-power-up-click
         (mf/use-fn
          (fn []
@@ -1393,7 +1422,8 @@
                                 :on-key-down (fn [event]
                                                (when (kbd/enter? event)
                                                  (on-menu-click event)))
-                                :on-pointer-enter on-menu-click
+                                :on-pointer-enter on-menu-pointer-enter
+                                :on-pointer-leave on-menu-pointer-leave
                                 :data-testid "help-learning"
                                 :id          "help-learning"}
         [:span {:class (stl/css :item-name)} (tr "labels.help-learning")]
@@ -1404,7 +1434,8 @@
                                 :on-key-down (fn [event]
                                                (when (kbd/enter? event)
                                                  (on-menu-click event)))
-                                :on-pointer-enter on-menu-click
+                                :on-pointer-enter on-menu-pointer-enter
+                                :on-pointer-leave on-menu-pointer-leave
                                 :data-testid "community-contributions"
                                 :id          "community-contributions"}
         [:span {:class (stl/css :item-name)} (tr "labels.community-contributions")]
@@ -1415,7 +1446,8 @@
                                 :on-key-down (fn [event]
                                                (when (kbd/enter? event)
                                                  (on-menu-click event)))
-                                :on-pointer-enter on-menu-click
+                                :on-pointer-enter on-menu-pointer-enter
+                                :on-pointer-leave on-menu-pointer-leave
                                 :data-testid "about-penpot"
                                 :id          "about-penpot"}
 
@@ -1440,13 +1472,20 @@
      (when show-profile-menu?
        (case sub-menu
          :help-learning
-         [:> help-learning-menu* {:on-close close-sub-menu :on-click on-click}]
+         [:> help-learning-menu* {:on-close close-sub-menu
+                                  :on-click on-click
+                                  :on-pointer-enter on-sub-menu-pointer-enter
+                                  :on-pointer-leave on-menu-pointer-leave}]
 
          :community-contributions
-         [:> community-contributions-menu* {:on-close close-sub-menu}]
+         [:> community-contributions-menu* {:on-close close-sub-menu
+                                            :on-pointer-enter on-sub-menu-pointer-enter
+                                            :on-pointer-leave on-menu-pointer-leave}]
 
          :about-penpot
-         [:> about-penpot-menu* {:on-close close-sub-menu}]
+         [:> about-penpot-menu* {:on-close close-sub-menu
+                                 :on-pointer-enter on-sub-menu-pointer-enter
+                                 :on-pointer-leave on-menu-pointer-leave}]
          nil))]))
 
 (mf/defc sidebar*