diff --git a/packages/menu/src/Menu.ts b/packages/menu/src/Menu.ts
index a26acdaa06..4d4e7f70e2 100644
--- a/packages/menu/src/Menu.ts
+++ b/packages/menu/src/Menu.ts
@@ -591,7 +591,8 @@ export class Menu extends SizedMixin(SpectrumElement) {
         const focusedItem = this.childItems[this.focusedItemIndex];
         if (focusedItem) {
             focusedItem.focused = false;
-            focusedItem.active = false;
+            // Remain active while a submenu is opened.
+            focusedItem.active = focusedItem.open;
         }
         this.focusedItemIndex =
             (this.childItems.length + this.focusedItemIndex + offset) %
diff --git a/packages/menu/src/MenuItem.ts b/packages/menu/src/MenuItem.ts
index c10ad560fa..e840f6584d 100644
--- a/packages/menu/src/MenuItem.ts
+++ b/packages/menu/src/MenuItem.ts
@@ -369,6 +369,14 @@ export class MenuItem extends LikeAnchor(
         this.openOverlay();
     }
 
+    protected handleSubmenuFocus(): void {
+        requestAnimationFrame(() => {
+            // Wait till after `closeDescendentOverlays` has happened in Menu
+            // to reopen (keey open) the direct descendent of this Menu Item
+            this.overlayElement.open = this.open;
+        });
+    }
+
     protected handlePointerenter(): void {
         if (this.leaveTimeout) {
             clearTimeout(this.leaveTimeout);
@@ -512,6 +520,11 @@ export class MenuItem extends LikeAnchor(
                     this.handleSubmenuClick,
                     options
                 );
+                this.addEventListener(
+                    'focus',
+                    this.handleSubmenuFocus,
+                    options
+                );
                 this.addEventListener(
                     'pointerenter',
                     this.handlePointerenter,
diff --git a/packages/overlay/src/topLayerOverTransforms.ts b/packages/overlay/src/topLayerOverTransforms.ts
index 5e2c763bcc..a721d9339b 100644
--- a/packages/overlay/src/topLayerOverTransforms.ts
+++ b/packages/overlay/src/topLayerOverTransforms.ts
@@ -14,6 +14,7 @@ import {
     getContainingBlock,
     getWindow,
     isContainingBlock,
+    isWebKit,
 } from '@floating-ui/utils/dom';
 import { VirtualTrigger } from './VirtualTrigger.js';
 
@@ -79,7 +80,9 @@ export const topLayerOverTransforms = (): Middleware => ({
                 const css = getComputedStyle(containingBlock);
                 overTransforms =
                     withinReference &&
-                    (css.transform !== 'none' || css.filter !== 'none');
+                    (css.transform !== 'none' ||
+                        (!isWebKit() &&
+                            (css.filter ? css.filter !== 'none' : false)));
             }
 
             if (onTopLayer && overTransforms && containingBlock) {
diff --git a/packages/overlay/stories/overlay-element.stories.ts b/packages/overlay/stories/overlay-element.stories.ts
index ed271a5fc9..e4dc8f5f85 100644
--- a/packages/overlay/stories/overlay-element.stories.ts
+++ b/packages/overlay/stories/overlay-element.stories.ts
@@ -167,11 +167,24 @@ export const actionGroup = ({ delayed }: Properties): TemplateResult => {
     return html`
         <style>
             sp-popover sp-action-group {
-                padding: var(--spectrum-actiongroup-vertical-spacing-regular);
+                padding: calc(
+                        var(--spectrum-actiongroup-vertical-spacing-regular) *
+                            0.75
+                    )
+                    calc(
+                        var(--spectrum-actiongroup-vertical-spacing-regular) / 2
+                    );
             }
             .root {
-                inset-inline-end: 3em;
+                inset-inline-end: 0em;
                 inset-block-start: 3em;
+                padding-block-end: 3em;
+                overflow: hidden;
+            }
+            .root > sp-action-group > sp-action-button,
+            .root > sp-action-group > sp-action-menu {
+                top: 3em;
+                position: relative;
             }
         </style>
         <sp-popover open class="root">
@@ -187,6 +200,41 @@ export const actionGroup = ({ delayed }: Properties): TemplateResult => {
                 <sp-action-button id="trigger-3" hold-affordance>
                     <sp-icon-rect-select slot="icon"></sp-icon-rect-select>
                 </sp-action-button>
+                <sp-action-menu placement="left">
+                    <sp-menu-group id="cms">
+                        <span slot="header">cms</span>
+                        <sp-menu-item value="updateAllSiteContent">
+                            Update All Content
+                        </sp-menu-item>
+                        <sp-menu-item value="refreshAllXDs">
+                            Refresh All XDs
+                        </sp-menu-item>
+                    </sp-menu-group>
+                    <sp-menu-group id="ssg">
+                        <span slot="header">ssg</span>
+                        <sp-menu-item value="clearCache">
+                            Clear Cache
+                        </sp-menu-item>
+                    </sp-menu-group>
+                    <sp-menu-group id="vrt">
+                        <span slot="header">vrt</span>
+                        <sp-menu-item value="vrt-contributions">
+                            Contributions
+                        </sp-menu-item>
+                        <sp-menu-item value="vrt-internal">
+                            Internal
+                        </sp-menu-item>
+                        <sp-menu-item value="vrt-public">Public</sp-menu-item>
+                        <sp-menu-item value="vrt-patterns">
+                            Patterns
+                        </sp-menu-item>
+                        <sp-menu-item value="vrt">All</sp-menu-item>
+                    </sp-menu-group>
+                    <sp-menu-divider></sp-menu-divider>
+                    <sp-menu-group id="misc">
+                        <sp-menu-item value="logout">Logout</sp-menu-item>
+                    </sp-menu-group>
+                </sp-action-menu>
             </sp-action-group>
         </sp-popover>
         <sp-overlay ?delayed=${delayed} trigger="trigger-1@hover">
@@ -280,13 +328,27 @@ export const actionGroupWithFilters = ({
     return html`
         <style>
             sp-popover sp-action-group {
-                padding: var(--spectrum-actiongroup-vertical-spacing-regular);
+                padding: calc(
+                        var(--spectrum-actiongroup-vertical-spacing-regular) *
+                            0.75
+                    )
+                    calc(
+                        var(--spectrum-actiongroup-vertical-spacing-regular) / 2
+                    );
             }
             .root {
-                inset-inline-end: 3em;
+                inset-inline-end: 0em;
                 inset-block-start: 3em;
+                padding-block-end: 3em;
+                overflow: hidden;
+            }
+            .root > sp-action-group > sp-action-button,
+            .root > sp-action-group > sp-action-menu {
+                top: 3em;
+                position: relative;
             }
-            sp-action-button {
+            sp-action-button,
+            sp-action-menu {
                 background-image: linear-gradient(
                     rgba(125, 125, 125, 0.2),
                     rgba(125, 125, 125, 0.2)
@@ -340,6 +402,41 @@ export const actionGroupWithFilters = ({
                         Hover
                     </sp-tooltip>
                 </sp-action-button>
+                <sp-action-menu>
+                    <sp-menu-group id="cms">
+                        <span slot="header">cms</span>
+                        <sp-menu-item value="updateAllSiteContent">
+                            Update All Content
+                        </sp-menu-item>
+                        <sp-menu-item value="refreshAllXDs">
+                            Refresh All XDs
+                        </sp-menu-item>
+                    </sp-menu-group>
+                    <sp-menu-group id="ssg">
+                        <span slot="header">ssg</span>
+                        <sp-menu-item value="clearCache">
+                            Clear Cache
+                        </sp-menu-item>
+                    </sp-menu-group>
+                    <sp-menu-group id="vrt">
+                        <span slot="header">vrt</span>
+                        <sp-menu-item value="vrt-contributions">
+                            Contributions
+                        </sp-menu-item>
+                        <sp-menu-item value="vrt-internal">
+                            Internal
+                        </sp-menu-item>
+                        <sp-menu-item value="vrt-public">Public</sp-menu-item>
+                        <sp-menu-item value="vrt-patterns">
+                            Patterns
+                        </sp-menu-item>
+                        <sp-menu-item value="vrt">All</sp-menu-item>
+                    </sp-menu-group>
+                    <sp-menu-divider></sp-menu-divider>
+                    <sp-menu-group id="misc">
+                        <sp-menu-item value="logout">Logout</sp-menu-item>
+                    </sp-menu-group>
+                </sp-action-menu>
             </sp-action-group>
         </sp-popover>
         <sp-overlay ?delayed=${delayed} trigger="trigger-2@hover">