diff --git a/client/scss/components/_pill.scss b/client/scss/components/_pill.scss
index 70ec41efef..75f4501648 100644
--- a/client/scss/components/_pill.scss
+++ b/client/scss/components/_pill.scss
@@ -7,6 +7,10 @@
   }
 
   &__remove {
-    @apply w-pr-3 w-py-1 w-rounded-r-xl w-border w-border-info-100 w-bg-info-100 hover:w-bg-info-125 w-text-white hover:w-text-white w-p-0 w-pl-2 w-flex w-items-center w-justify-center w-h-full;
+    @apply w-pr-3 w-py-1 w-rounded-r-xl w-border w-border-info-100 w-bg-info-100 w-text-white w-p-0 w-pl-2 w-flex w-items-center w-justify-center w-h-full;
+  }
+
+  button {
+    @apply hover:w-bg-info-125;
   }
 }
diff --git a/client/src/controllers/DrilldownController.ts b/client/src/controllers/DrilldownController.ts
index a227b03e7d..f1c4886e8b 100644
--- a/client/src/controllers/DrilldownController.ts
+++ b/client/src/controllers/DrilldownController.ts
@@ -1,4 +1,6 @@
 import { Controller } from '@hotwired/stimulus';
+import { ActionController } from './ActionController';
+import { DropdownController } from './DropdownController';
 
 /**
  * Drilldown menu interaction combined with URL-driven
@@ -13,17 +15,44 @@ export class DrilldownController extends Controller<HTMLElement> {
     countAttr: { default: '', type: String },
   };
 
+  static outlets = [
+    // w-action outlet for submenu toggles that are outside the drilldown.
+    // We don't really use anything specific to ActionController, we just need
+    // a Stimulus controller to be able to use the outlet. As with toggle targets,
+    // these need to have aria-controls.
+    'w-action',
+
+    // w-dropdown outlet for the popup menu, to allow interacting with the
+    // DropdownController programmatically.
+    'w-dropdown',
+  ];
+
   declare activeSubmenuValue: string;
   declare countAttrValue: string;
 
   declare readonly countTargets: HTMLElement[];
   declare readonly menuTarget: HTMLElement;
   declare readonly toggleTargets: HTMLButtonElement[];
+  declare readonly hasWDropdownOutlet: boolean;
+  declare readonly wActionOutlets: ActionController[];
+  declare readonly wDropdownOutlet: DropdownController;
 
   countTargetConnected() {
     this.updateCount();
   }
 
+  connect(): void {
+    this.open = this.open.bind(this);
+  }
+
+  wActionOutletConnected(_: ActionController, element: HTMLElement) {
+    element.addEventListener('click', this.open);
+  }
+
+  wActionOutletDisconnected(_: ActionController, element: HTMLElement) {
+    element.removeEventListener('click', this.open);
+  }
+
   /**
    * Update the count of items in the menu.
    * This is done by counting the number of elements with the data attribute
@@ -107,7 +136,33 @@ export class DrilldownController extends Controller<HTMLElement> {
     }
   }
 
+  /**
+   * Prevent clicks on the w-action outlets from closing the dropdown.
+   * Usage: data-action="w-dropdown:clickaway->w-drilldown#preventOutletClickaway"
+   */
+  preventOutletClickaway(e: Event) {
+    const clickawayEvent = e as CustomEvent<{ target: HTMLElement }>;
+    const target = clickawayEvent.detail.target;
+    if (!target) return;
+    const controlledIds = this.toggleTargets.map((toggle) =>
+      toggle.getAttribute('aria-controls'),
+    );
+    const clickawayControl =
+      target.closest('button')?.getAttribute('aria-controls') || '';
+    if (controlledIds.includes(clickawayControl)) {
+      e.preventDefault();
+    }
+  }
+
   toggle(expanded: boolean, toggle: HTMLButtonElement) {
+    // If we're expanding, the toggle may be inside the w-dropdown outlet while
+    // the dropdown is hidden (e.g. opening directly to a submenu from an
+    // overall collapsed state).
+    // Ensure that the dropdown is shown so Tippy renders the toggle in the DOM.
+    if (this.hasWDropdownOutlet && expanded) {
+      this.wDropdownOutlet.show();
+    }
+
     const controls = toggle.getAttribute('aria-controls');
     const content = this.element.querySelector<HTMLElement>(`#${controls}`);
     if (!content) {
diff --git a/wagtail/admin/templates/wagtailadmin/shared/active_filters.html b/wagtail/admin/templates/wagtailadmin/shared/active_filters.html
index 6d79509bfc..ba665da817 100644
--- a/wagtail/admin/templates/wagtailadmin/shared/active_filters.html
+++ b/wagtail/admin/templates/wagtailadmin/shared/active_filters.html
@@ -1,11 +1,11 @@
 {% load i18n wagtailadmin_tags %}
 <ul class="w-active-filters">
     {% for filter in active_filters %}
-        <li class="w-pill" data-w-active-filter-name="{{ filter.auto_id }}">
-            <div class="w-pill__content">
+        <li class="w-pill">
+            <button class="w-pill__content" data-controller="w-action" data-w-active-filter-name="{{ filter.auto_id }}" aria-controls="drilldown-{{ filter.auto_id }}">
                 <span class="w-text-14">{{ filter.field_label }}:</span>
                 <b class="w-ml-1">{{ filter.value }}</b>
-            </div>
+            </button>
             <button
                 data-controller="w-swap"
                 data-action="click->w-swap#replaceLazy"
diff --git a/wagtail/admin/templates/wagtailadmin/shared/headers/slim_header.html b/wagtail/admin/templates/wagtailadmin/shared/headers/slim_header.html
index 8fc44b9cff..cae299f69d 100644
--- a/wagtail/admin/templates/wagtailadmin/shared/headers/slim_header.html
+++ b/wagtail/admin/templates/wagtailadmin/shared/headers/slim_header.html
@@ -79,7 +79,15 @@
                         {% endif %}
 
                         {% if filters %}
-                            <div id="filters-drilldown" class="w-drilldown" data-controller="w-drilldown" data-action="w-swap:success@document->w-drilldown#updateParams w-dropdown:hide->w-drilldown#delayedClose" data-w-drilldown-count-attr-value="data-w-active-filter-name">
+                            <div
+                                id="filters-drilldown"
+                                class="w-drilldown"
+                                data-controller="w-drilldown"
+                                data-action="w-swap:success@document->w-drilldown#updateParams w-dropdown:hide->w-drilldown#delayedClose w-dropdown:clickaway->w-drilldown#preventOutletClickaway"
+                                data-w-drilldown-count-attr-value="data-w-active-filter-name"
+                                data-w-drilldown-w-action-outlet="[data-w-active-filter-name][data-controller='w-action']"
+                                data-w-drilldown-w-dropdown-outlet="#filters-drilldown [data-controller='w-dropdown']"
+                            >
                                 {% include "wagtailadmin/shared/headers/_filters.html" with filters=filters only %}
                             </div>
                         {% endif %}