diff --git a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingActions.ts b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingActions.ts
index 8a2ac519e78dd..9e4102b583845 100644
--- a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingActions.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingActions.ts
@@ -98,6 +98,11 @@ registerAction2(class RemoveFileFromWorkingSet extends WorkingSetAction {
 				order: 5,
 				group: 'navigation'
 			}],
+			keybinding: {
+				primary: KeyCode.Delete,
+				when: ContextKeyExpr.and(ChatContextKeys.location.isEqualTo(ChatAgentLocation.EditingSession), ChatContextKeys.inChatEditWorkingSet),
+				weight: KeybindingWeight.WorkbenchContrib,
+			}
 		});
 	}
 
diff --git a/src/vs/workbench/contrib/chat/browser/chatInputPart.ts b/src/vs/workbench/contrib/chat/browser/chatInputPart.ts
index cc9ebf1b7baff..3dad10ec25c74 100644
--- a/src/vs/workbench/contrib/chat/browser/chatInputPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatInputPart.ts
@@ -149,6 +149,8 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 	readonly onDidAcceptFollowup = this._onDidAcceptFollowup.event;
 
 	private readonly _attachmentModel: ChatAttachmentModel;
+	private _inChatEditWorkingSetCtx: IContextKey<boolean> | undefined;
+
 	public get attachmentModel(): ChatAttachmentModel {
 		return this._attachmentModel;
 	}
@@ -643,6 +645,8 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		ChatContextKeys.inChatInput.bindTo(inputScopedContextKeyService).set(true);
 		const scopedInstantiationService = this._register(this.instantiationService.createChild(new ServiceCollection([IContextKeyService, inputScopedContextKeyService])));
 
+		this._inChatEditWorkingSetCtx = ChatContextKeys.inChatEditWorkingSet.bindTo(this.contextKeyService);
+
 		const { historyNavigationBackwardsEnablement, historyNavigationForwardsEnablement } = this._register(registerAndCreateHistoryNavigationContext(inputScopedContextKeyService, this));
 		this.historyNavigationBackwardsEnablement = historyNavigationBackwardsEnablement;
 		this.historyNavigationForewardsEnablement = historyNavigationForwardsEnablement;
@@ -1268,6 +1272,8 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 
 		// Working set
 		const workingSetContainer = innerContainer.querySelector('.chat-editing-session-list') as HTMLElement ?? dom.append(innerContainer, $('.chat-editing-session-list'));
+		this._register(addDisposableListener(workingSetContainer, 'focusin', () => this._inChatEditWorkingSetCtx?.set(true)));
+		this._register(addDisposableListener(workingSetContainer, 'focusout', () => this._inChatEditWorkingSetCtx?.set(false)));
 		if (!this._chatEditList) {
 			this._chatEditList = this._chatEditsListPool.get();
 			const list = this._chatEditList.object;
diff --git a/src/vs/workbench/contrib/chat/common/chatContextKeys.ts b/src/vs/workbench/contrib/chat/common/chatContextKeys.ts
index 68c50c90600a0..e9fa7f0ac91af 100644
--- a/src/vs/workbench/contrib/chat/common/chatContextKeys.ts
+++ b/src/vs/workbench/contrib/chat/common/chatContextKeys.ts
@@ -28,6 +28,7 @@ export namespace ChatContextKeys {
 	export const inputHasFocus = new RawContextKey<boolean>('chatInputHasFocus', false, { type: 'boolean', description: localize('interactiveInputHasFocus', "True when the chat input has focus.") });
 	export const inChatInput = new RawContextKey<boolean>('inChatInput', false, { type: 'boolean', description: localize('inInteractiveInput', "True when focus is in the chat input, false otherwise.") });
 	export const inChatSession = new RawContextKey<boolean>('inChat', false, { type: 'boolean', description: localize('inChat', "True when focus is in the chat widget, false otherwise.") });
+	export const inChatEditWorkingSet = new RawContextKey<boolean>('inChatEditWorkingSet', false, { type: 'boolean', description: localize('inChatEditWorkingSet', "True when focus is in the chat edit working set, false otherwise.") });
 
 	export const supported = ContextKeyExpr.or(IsWebContext.toNegated(), RemoteNameContext.notEqualsTo('')); // supported on desktop and in web only with a remote connection
 	export const enabled = new RawContextKey<boolean>('chatIsEnabled', false, { type: 'boolean', description: localize('chatIsEnabled', "True when chat is enabled because a default chat participant is activated with an implementation.") });