diff --git a/src/vs/sessions/contrib/chat/browser/media/chatWidget.css b/src/vs/sessions/contrib/chat/browser/media/chatWidget.css
index 0ecc09577d9..785c0773b33 100644
--- a/src/vs/sessions/contrib/chat/browser/media/chatWidget.css
+++ b/src/vs/sessions/contrib/chat/browser/media/chatWidget.css
@@ -116,33 +116,59 @@
 	font-size: 16px;
 }
 
-/* Attach context button */
+/* Attach context button (matches AddFilesButton from chatInputPart) */
 .sessions-chat-attach-button {
 	display: flex;
 	align-items: center;
-	justify-content: center;
-	width: 26px;
-	height: 26px;
-	border-radius: 4px;
-	cursor: pointer;
-	color: var(--vscode-descriptionForeground);
-	background: transparent;
-	border: none;
-	outline: none;
 }
 
-.sessions-chat-attach-button:hover {
+.sessions-chat-attach-button.chat-attachment-button .action-label {
+	display: flex;
+	overflow: hidden;
+	font-size: 11px;
+	padding: 0 4px;
+	border: 1px solid var(--vscode-chat-requestBorder, var(--vscode-input-background, transparent));
+	border-radius: 4px;
+	height: 18px;
+	max-width: 100%;
+	width: fit-content;
+	cursor: pointer;
+	color: var(--vscode-descriptionForeground);
+	text-decoration: none;
+	align-items: center;
+	gap: 2px;
+	white-space: nowrap;
+}
+
+.sessions-chat-attach-button.chat-attachment-button .action-label:hover {
 	background-color: var(--vscode-toolbar-hoverBackground);
 	color: var(--vscode-foreground);
 }
 
-.sessions-chat-attach-button:focus-visible {
+.sessions-chat-attach-button.chat-attachment-button .action-label:focus-visible {
 	outline: 1px solid var(--vscode-focusBorder);
 	outline-offset: -1px;
 }
 
-.sessions-chat-attach-button .codicon {
-	font-size: 16px;
+.sessions-chat-attach-button.chat-attachment-button .action-label > .codicon {
+	font-size: 14px;
+	height: auto;
+}
+
+.sessions-chat-attach-button.chat-attachment-button .action-label:not(.has-label) {
+	display: flex;
+	align-items: center;
+	justify-content: center;
+	padding: 2px 4px;
+	height: fit-content;
+	gap: 0;
+	border: 1px solid var(--vscode-chat-requestBorder, var(--vscode-input-background, transparent));
+	border-radius: 4px;
+	box-sizing: border-box;
+}
+
+.sessions-chat-attach-button.chat-attachment-button .action-label:not(.has-label) .codicon {
+	width: 14px;
 }
 
 /* Attached context container */
diff --git a/src/vs/sessions/contrib/chat/browser/newChatViewPane.ts b/src/vs/sessions/contrib/chat/browser/newChatViewPane.ts
index bef050ad7fa..baa93c3d156 100644
--- a/src/vs/sessions/contrib/chat/browser/newChatViewPane.ts
+++ b/src/vs/sessions/contrib/chat/browser/newChatViewPane.ts
@@ -32,7 +32,7 @@ import { IOpenerService } from '../../../../platform/opener/common/opener.js';
 import { IThemeService } from '../../../../platform/theme/common/themeService.js';
 import { IHoverService } from '../../../../platform/hover/browser/hover.js';
 import { HoverPosition } from '../../../../base/browser/ui/hover/hoverWidget.js';
-import { renderIcon } from '../../../../base/browser/ui/iconLabel/iconLabels.js';
+import { renderIcon, renderLabelWithIcons } from '../../../../base/browser/ui/iconLabel/iconLabels.js';
 import { basename, isEqual } from '../../../../base/common/resources.js';
 import { localize } from '../../../../nls.js';
 import { AgentSessionProviders } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessions.js';
@@ -198,6 +198,7 @@ class NewChatWidget extends Disposable {
 	// Input
 	private _editor!: CodeEditorWidget;
 	private readonly _currentLanguageModel = observableValue<ILanguageModelChatMetadataAndIdentifier | undefined>('currentLanguageModel', undefined);
+	private _updateAddContextButtonLabel: (() => void) | undefined;
 	private readonly _modelPickerDisposable = this._register(new MutableDisposable());
 	private _pendingSessionResource: URI | undefined;
 
@@ -439,14 +440,9 @@ class NewChatWidget extends Disposable {
 	private _createToolbar(container: HTMLElement): void {
 		const toolbar = dom.append(container, dom.$('.sessions-chat-toolbar'));
 
-		// Plus button for attaching context
-		const attachButton = dom.append(toolbar, dom.$('.sessions-chat-attach-button'));
-		attachButton.tabIndex = 0;
-		attachButton.role = 'button';
-		attachButton.title = localize('addContext', "Add Context...");
-		attachButton.ariaLabel = localize('addContext', "Add Context...");
-		dom.append(attachButton, renderIcon(Codicon.add));
-		this._register(dom.addDisposableListener(attachButton, dom.EventType.CLICK, () => this._showAttachContextPicker()));
+		// Add context button (matches AddFilesButton from chatInputPart)
+		const attachContainer = dom.append(toolbar, dom.$('.sessions-chat-attach-button'));
+		this._renderAddContextButton(attachContainer);
 
 		const modelPickerContainer = dom.append(toolbar, dom.$('.sessions-chat-model-picker'));
 		this._createModelPicker(modelPickerContainer);
@@ -461,6 +457,29 @@ class NewChatWidget extends Disposable {
 		this._register(dom.addDisposableListener(sendButton, dom.EventType.CLICK, () => this._send()));
 	}
 
+	private _renderAddContextButton(container: HTMLElement): void {
+		container.classList.add('chat-attachment-button');
+
+		const label = dom.append(container, dom.$('a.action-label'));
+		label.tabIndex = 0;
+		label.role = 'button';
+		label.ariaLabel = localize('addContext', "Add Context...");
+
+		const updateLabel = () => {
+			const hasAttachments = this._attachedContext.length > 0;
+			label.classList.toggle('has-label', !hasAttachments);
+			const message = !hasAttachments
+				? `$(attach) ${localize('addContext.label', "Add Context...")}`
+				: '$(attach)';
+			dom.reset(label, ...renderLabelWithIcons(message));
+		};
+
+		updateLabel();
+		this._updateAddContextButtonLabel = updateLabel;
+
+		this._register(dom.addDisposableListener(label, dom.EventType.CLICK, () => this._showAttachContextPicker()));
+	}
+
 	// --- Model picker ---
 
 	private _createModelPicker(container: HTMLElement): void {
@@ -576,6 +595,7 @@ class NewChatWidget extends Disposable {
 		}
 
 		dom.clearNode(this._attachedContextContainer);
+		this._updateAddContextButtonLabel?.();
 
 		if (this._attachedContext.length === 0) {
 			this._attachedContextContainer.style.display = 'none';