diff --git a/src/vs/workbench/contrib/chat/browser/actions/chatSessionActions.ts b/src/vs/workbench/contrib/chat/browser/actions/chatSessionActions.ts
index 3beb481833c1..c3b1f8195f6e 100644
--- a/src/vs/workbench/contrib/chat/browser/actions/chatSessionActions.ts
+++ b/src/vs/workbench/contrib/chat/browser/actions/chatSessionActions.ts
@@ -441,7 +441,10 @@ MenuRegistry.appendMenuItem(MenuId.ChatSessionsMenu, {
 	},
 	group: 'inline',
 	order: 1,
-	when: ChatContextKeys.sessionType.isEqualTo(localChatSessionType)
+	when: ContextKeyExpr.and(
+		ChatContextKeys.sessionType.isEqualTo(localChatSessionType),
+		ChatContextKeys.isCombinedSessionViewer.negate()
+	)
 });
 
 // Register delete menu item - only show for non-active sessions (history items)
diff --git a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsView.ts b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsView.ts
index 766335bd7f48..913bd2a6a7db 100644
--- a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsView.ts
+++ b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsView.ts
@@ -44,13 +44,14 @@ import { Event } from '../../../../../base/common/event.js';
 import { MutableDisposable } from '../../../../../base/common/lifecycle.js';
 import { ITreeContextMenuEvent } from '../../../../../base/browser/ui/tree/tree.js';
 import { MarshalledId } from '../../../../../base/common/marshallingIds.js';
-import { getActionBarActions } from '../../../../../platform/actions/browser/menuEntryActionViewItem.js';
+import { getActionBarActions, getFlatActionBarActions } from '../../../../../platform/actions/browser/menuEntryActionViewItem.js';
 import { IChatService } from '../../common/chatService.js';
 import { IChatWidgetService } from '../chat.js';
 import { AGENT_SESSIONS_VIEW_ID, AGENT_SESSIONS_VIEW_CONTAINER_ID, AgentSessionProviders } from './agentSessions.js';
 import { TreeFindMode } from '../../../../../base/browser/ui/tree/abstractTree.js';
 import { SIDE_GROUP } from '../../../../services/editor/common/editorService.js';
 import { IMarshalledChatSessionContext } from '../actions/chatSessionActions.js';
+import { distinct } from '../../../../../base/common/arrays.js';
 
 export class AgentSessionsView extends ViewPane {
 
@@ -158,18 +159,13 @@ export class AgentSessionsView extends ViewPane {
 		}
 
 		const provider = await this.chatSessionsService.activateChatSessionItemProvider(session.providerType);
-
-		const menu = this.menuService.createMenu(MenuId.ChatSessionsMenu, this.contextKeyService.createOverlay(getSessionItemContextOverlay(
-			session,
-			provider,
-			this.chatWidgetService,
-			this.chatService,
-			this.editorGroupsService
-		)));
+		const contextOverlay = getSessionItemContextOverlay(session, provider, this.chatWidgetService, this.chatService, this.editorGroupsService);
+		contextOverlay.push([ChatContextKeys.isCombinedSessionViewer.key, true]);
+		const menu = this.menuService.createMenu(MenuId.ChatSessionsMenu, this.contextKeyService.createOverlay(contextOverlay));
 
 		const marshalledSession: IMarshalledChatSessionContext = { session, $mid: MarshalledId.ChatSessionContext };
-		const { secondary } = getActionBarActions(menu.getActions({ arg: marshalledSession, shouldForwardArgs: true }), 'inline'); this.contextMenuService.showContextMenu({
-			getActions: () => secondary,
+		this.contextMenuService.showContextMenu({
+			getActions: () => distinct(getFlatActionBarActions(menu.getActions({ arg: marshalledSession, shouldForwardArgs: true })), action => action.id),
 			getAnchor: () => anchor,
 			getActionsContext: () => marshalledSession,
 		});
diff --git a/src/vs/workbench/contrib/chat/browser/chatSessions/view/sessionsViewPane.ts b/src/vs/workbench/contrib/chat/browser/chatSessions/view/sessionsViewPane.ts
index 34c92c5682ce..f8dd87df0669 100644
--- a/src/vs/workbench/contrib/chat/browser/chatSessions/view/sessionsViewPane.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatSessions/view/sessionsViewPane.ts
@@ -512,7 +512,8 @@ export class SessionsViewPane extends ViewPane {
 		// Get actions and filter for context menu (all actions that are NOT inline)
 		const actions = menu.getActions({ arg: marshalledSession, shouldForwardArgs: true });
 
-		const { secondary } = getActionBarActions(actions, 'inline'); this.contextMenuService.showContextMenu({
+		const { secondary } = getActionBarActions(actions, 'inline');
+		this.contextMenuService.showContextMenu({
 			getActions: () => secondary,
 			getAnchor: () => e.anchor,
 			getActionsContext: () => marshalledSession,
diff --git a/src/vs/workbench/contrib/chat/common/chatContextKeys.ts b/src/vs/workbench/contrib/chat/common/chatContextKeys.ts
index d5ab4e32dda5..68b89136a212 100644
--- a/src/vs/workbench/contrib/chat/common/chatContextKeys.ts
+++ b/src/vs/workbench/contrib/chat/common/chatContextKeys.ts
@@ -93,6 +93,7 @@ export namespace ChatContextKeys {
 
 	export const sessionType = new RawContextKey<string>('chatSessionType', '', { type: 'string', description: localize('chatSessionType', "The type of the current chat session item.") });
 	export const isArchivedItem = new RawContextKey<boolean>('chatIsArchivedItem', false, { type: 'boolean', description: localize('chatIsArchivedItem', "True when the chat session item is archived.") });
+	export const isCombinedSessionViewer = new RawContextKey<boolean>('chatIsCombinedSessionViewer', false, { type: 'boolean', description: localize('chatIsCombinedSessionViewer', "True when the chat session viewer uses the new combined style.") }); // TODO@bpasero eventually retire this context key
 	export const isActiveSession = new RawContextKey<boolean>('chatIsActiveSession', false, { type: 'boolean', description: localize('chatIsActiveSession', "True when the chat session is currently active (not deletable).") });
 	export const isKatexMathElement = new RawContextKey<boolean>('chatIsKatexMathElement', false, { type: 'boolean', description: localize('chatIsKatexMathElement', "True when focusing a KaTeX math element.") });
 }