diff --git a/src/vs/workbench/contrib/terminal/common/terminalContextKey.ts b/src/vs/workbench/contrib/terminal/common/terminalContextKey.ts
index 78fd7df6712..7f777f94f62 100644
--- a/src/vs/workbench/contrib/terminal/common/terminalContextKey.ts
+++ b/src/vs/workbench/contrib/terminal/common/terminalContextKey.ts
@@ -43,6 +43,7 @@ export const enum TerminalContextKeyStrings {
 	ChatVisible = 'terminalChatVisible',
 	ChatActiveRequest = 'terminalChatActiveRequest',
 	ChatInputHasText = 'terminalChatInputHasText',
+	ChatAgentRegistered = 'terminalChatAgentRegistered',
 }
 
 export namespace TerminalContextKeys {
@@ -175,4 +176,7 @@ export namespace TerminalContextKeys {
 
 	/** Whether the chat input has text */
 	export const chatInputHasText = new RawContextKey<boolean>(TerminalContextKeyStrings.ChatInputHasText, false, localize('chatInputHasTextContextKey', "Whether the chat input has text."));
+
+	/** Whether the terminal chat agent has been registered */
+	export const chatAgentRegistered = new RawContextKey<boolean>(TerminalContextKeyStrings.ChatAgentRegistered, false, localize('chatAgentRegisteredContextKey', "Whether the terminal chat agent has been registered."));
 }
diff --git a/src/vs/workbench/contrib/terminalContrib/chat/browser/terminalChatActions.ts b/src/vs/workbench/contrib/terminalContrib/chat/browser/terminalChatActions.ts
index bb1a012026a..dcf2aec0617 100644
--- a/src/vs/workbench/contrib/terminalContrib/chat/browser/terminalChatActions.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chat/browser/terminalChatActions.ts
@@ -72,7 +72,8 @@ registerActiveXtermAction({
 	precondition: ContextKeyExpr.and(
 		ContextKeyExpr.has(`config.${TerminalSettingId.ExperimentalInlineChat}`),
 		ContextKeyExpr.or(TerminalContextKeys.processSupported, TerminalContextKeys.terminalHasBeenCreated),
-		TerminalContextKeys.chatRequestActive.negate()
+		TerminalContextKeys.chatRequestActive.negate(),
+		TerminalContextKeys.chatAgentRegistered
 	),
 	icon: Codicon.send,
 	keybinding: {
@@ -103,6 +104,7 @@ registerActiveXtermAction({
 	precondition: ContextKeyExpr.and(
 		ContextKeyExpr.has(`config.${TerminalSettingId.ExperimentalInlineChat}`),
 		TerminalContextKeys.chatRequestActive,
+		TerminalContextKeys.chatAgentRegistered
 	),
 	icon: Codicon.debugStop,
 	menu: {
diff --git a/src/vs/workbench/contrib/terminalContrib/chat/browser/terminalChatController.ts b/src/vs/workbench/contrib/terminalContrib/chat/browser/terminalChatController.ts
index 432d5fd0cbf..b3b9c002aad 100644
--- a/src/vs/workbench/contrib/terminalContrib/chat/browser/terminalChatController.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chat/browser/terminalChatController.ts
@@ -41,6 +41,7 @@ export class TerminalChatController extends Disposable implements ITerminalContr
 	get chatWidget(): TerminalChatWidget | undefined { return this._chatWidget?.value; }
 
 	private readonly _ctxHasActiveRequest!: IContextKey<boolean>;
+	private readonly _ctxHasTerminalAgent!: IContextKey<boolean>;
 
 	private _cancellationTokenSource!: CancellationTokenSource;
 
@@ -60,6 +61,16 @@ export class TerminalChatController extends Disposable implements ITerminalContr
 			return;
 		}
 		this._ctxHasActiveRequest = TerminalContextKeys.chatRequestActive.bindTo(this._contextKeyService);
+		this._ctxHasTerminalAgent = TerminalContextKeys.chatAgentRegistered.bindTo(this._contextKeyService);
+		if (!this._chatAgentService.hasAgent('terminal')) {
+			this._register(this._chatAgentService.onDidChangeAgents(() => {
+				if (this._chatAgentService.getAgent('terminal')) {
+					this._ctxHasTerminalAgent.set(true);
+				}
+			}));
+		} else {
+			this._ctxHasTerminalAgent.set(true);
+		}
 		this._cancellationTokenSource = new CancellationTokenSource();
 	}