diff --git a/src/vs/sessions/contrib/automations/browser/automationDialogService.ts b/src/vs/sessions/contrib/automations/browser/automationDialogService.ts
index 192f2c5b5e5e9..0fed1d6a25920 100644
--- a/src/vs/sessions/contrib/automations/browser/automationDialogService.ts
+++ b/src/vs/sessions/contrib/automations/browser/automationDialogService.ts
@@ -6,7 +6,7 @@
 import * as DOM from '../../../../base/browser/dom.js';
 import { IButton } from '../../../../base/browser/ui/button/button.js';
 import { Dialog } from '../../../../base/browser/ui/dialog/dialog.js';
-import { DisposableStore } from '../../../../base/common/lifecycle.js';
+import { DisposableStore, toDisposable } from '../../../../base/common/lifecycle.js';
 import { localize } from '../../../../nls.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
@@ -89,8 +89,9 @@ export class AutomationDialogService implements IAutomationDialogService {
 			localize('automation.dialog.cancel', "Cancel"),
 		];
 
+		const activeContainer = this.layoutService.activeContainer;
 		const dialog = disposables.add(new Dialog(
-			this.layoutService.activeContainer,
+			activeContainer,
 			title,
 			buttonLabels,
 			createWorkbenchDialogOptions({
@@ -133,6 +134,9 @@ export class AutomationDialogService implements IAutomationDialogService {
 			}, this.keybindingService, this.layoutService, this.hostService),
 		));
 
+		activeContainer.classList.add('automation-dialog-open');
+		disposables.add(toDisposable(() => activeContainer.classList.remove('automation-dialog-open')));
+
 		try {
 			const result = await dialog.show();
 			if (result.button !== 0) {
diff --git a/src/vs/workbench/contrib/chat/browser/aiCustomization/media/aiCustomizationManagement.css b/src/vs/workbench/contrib/chat/browser/aiCustomization/media/aiCustomizationManagement.css
index c235ca03e96b4..3812224c6f2bb 100644
--- a/src/vs/workbench/contrib/chat/browser/aiCustomization/media/aiCustomizationManagement.css
+++ b/src/vs/workbench/contrib/chat/browser/aiCustomization/media/aiCustomizationManagement.css
@@ -2348,20 +2348,18 @@ pane is first mounted. View switches inside the modal are not animated. */
  * contextview.ts as `2575 + layer`). DOM order means the dialog
  * shows on top, hiding any popup the chat input chips, the quick
  * input, or a context menu try to open. We can't change the inline
- * z-index from outside, so use `!important` on rules scoped to
- * `body:has(.automation-dialog)`. They only apply while the
- * automations dialog is on screen, so other dialogs' popup stacking
- * is untouched.
+ * z-index from outside, so use `!important` while the dialog service
+ * marks the active container as automation-dialog-open.
  */
-body:has(.automation-dialog) .context-view.monaco-component {
+.automation-dialog-open .context-view.monaco-component {
 	z-index: 2600 !important;
 }
 
-body:has(.automation-dialog) .quick-input-widget {
+.automation-dialog-open .quick-input-widget {
 	z-index: 2600 !important;
 }
 
-body:has(.automation-dialog) .monaco-menu-container {
+.automation-dialog-open .monaco-menu-container {
 	z-index: 2600 !important;
 }
 
@@ -2858,4 +2856,4 @@ body:has(.automation-dialog) .monaco-menu-container {
 	overflow: hidden;
 	text-overflow: ellipsis;
 	max-width: 240px;
-}
\ No newline at end of file
+}