diff --git a/site/src/pages/AgentsPage/AgentChatPage.tsx b/site/src/pages/AgentsPage/AgentChatPage.tsx
index 2f0c6aa01c..140599324c 100644
--- a/site/src/pages/AgentsPage/AgentChatPage.tsx
+++ b/site/src/pages/AgentsPage/AgentChatPage.tsx
@@ -470,6 +470,7 @@ type _UncoveredAgentFields = Omit<
 	| "status"
 	| "name"
 	| "expanded_directory"
+	| "lifecycle_state"
 	// Fields below are intentionally not compared. They change
 	// frequently (stats, metadata) or are objects/arrays that would
 	// require deep comparison, and the UI does not read them.
@@ -481,7 +482,6 @@ type _UncoveredAgentFields = Omit<
 	| "disconnected_at"
 	| "started_at"
 	| "ready_at"
-	| "lifecycle_state"
 	| "resource_id"
 	| "instance_id"
 	| "architecture"
@@ -641,7 +641,8 @@ const AgentChatPage: FC = () => {
 									prevAgent?.status === nextAgent?.status &&
 									prevAgent?.name === nextAgent?.name &&
 									prevAgent?.expanded_directory ===
-										nextAgent?.expanded_directory
+										nextAgent?.expanded_directory &&
+									prevAgent?.lifecycle_state === nextAgent?.lifecycle_state
 								) {
 									return prev;
 								}
diff --git a/site/src/pages/AgentsPage/AgentChatPageView.stories.tsx b/site/src/pages/AgentsPage/AgentChatPageView.stories.tsx
index ced1b0506f..c00958a329 100644
--- a/site/src/pages/AgentsPage/AgentChatPageView.stories.tsx
+++ b/site/src/pages/AgentsPage/AgentChatPageView.stories.tsx
@@ -5,7 +5,11 @@ import { reactRouterParameters } from "storybook-addon-remix-react-router";
 import { API } from "#/api/api";
 import type * as TypesGen from "#/api/typesGenerated";
 import type { ChatDiffStatus, ChatMessagePart } from "#/api/typesGenerated";
-import { MockUserOwner } from "#/testHelpers/entities";
+import {
+	MockUserOwner,
+	MockWorkspace,
+	MockWorkspaceAgent,
+} from "#/testHelpers/entities";
 import {
 	withAuthProvider,
 	withDashboardProvider,
@@ -373,6 +377,74 @@ export const WithWorkspaceActions: Story = {
 	),
 };
 
+// ---------------------------------------------------------------------------
+// Workspace status pill stories
+// ---------------------------------------------------------------------------
+
+export const WorkspaceAgentStarting: Story = {
+	render: () => (
+		<StoryAgentChatPageView
+			workspace={MockWorkspace}
+			workspaceAgent={{
+				...MockWorkspaceAgent,
+				lifecycle_state: "starting",
+			}}
+		/>
+	),
+};
+
+export const WorkspaceAgentCreated: Story = {
+	render: () => (
+		<StoryAgentChatPageView
+			workspace={MockWorkspace}
+			workspaceAgent={{
+				...MockWorkspaceAgent,
+				lifecycle_state: "created",
+			}}
+		/>
+	),
+};
+
+export const WorkspaceAgentReady: Story = {
+	render: () => (
+		<StoryAgentChatPageView
+			workspace={MockWorkspace}
+			workspaceAgent={{
+				...MockWorkspaceAgent,
+				lifecycle_state: "ready",
+			}}
+		/>
+	),
+};
+
+export const WorkspaceAgentStartError: Story = {
+	render: () => (
+		<StoryAgentChatPageView
+			workspace={MockWorkspace}
+			workspaceAgent={{
+				...MockWorkspaceAgent,
+				lifecycle_state: "start_error",
+			}}
+		/>
+	),
+};
+
+export const WorkspaceAgentStartTimeout: Story = {
+	render: () => (
+		<StoryAgentChatPageView
+			workspace={MockWorkspace}
+			workspaceAgent={{
+				...MockWorkspaceAgent,
+				lifecycle_state: "start_timeout",
+			}}
+		/>
+	),
+};
+
+export const WorkspaceNoAgent: Story = {
+	render: () => <StoryAgentChatPageView workspace={MockWorkspace} />,
+};
+
 // ---------------------------------------------------------------------------
 // AgentChatPageLoadingView stories
 // ---------------------------------------------------------------------------
diff --git a/site/src/pages/AgentsPage/AgentChatPageView.tsx b/site/src/pages/AgentsPage/AgentChatPageView.tsx
index 2056ba48c0..6655c4d27c 100644
--- a/site/src/pages/AgentsPage/AgentChatPageView.tsx
+++ b/site/src/pages/AgentsPage/AgentChatPageView.tsx
@@ -278,10 +278,25 @@ export const AgentChatPageView: FC<AgentChatPageViewProps> = ({
 
 	const attachedWorkspace = (() => {
 		if (!workspace || !workspaceRoute) return undefined;
-		const { type, text } = getDisplayWorkspaceStatus(
+		let { type, text } = getDisplayWorkspaceStatus(
 			workspace.latest_build.status,
 			workspace.latest_build.job,
 		);
+		const agentPreparing =
+			workspace.latest_build.status === "running" &&
+			(workspaceAgent?.lifecycle_state === "created" ||
+				workspaceAgent?.lifecycle_state === "starting");
+		const agentStartupFailed =
+			workspace.latest_build.status === "running" &&
+			(workspaceAgent?.lifecycle_state === "start_error" ||
+				workspaceAgent?.lifecycle_state === "start_timeout");
+		if (agentPreparing) {
+			type = "active";
+			text = "Preparing";
+		} else if (agentStartupFailed) {
+			type = "warning";
+			text = "Startup failed";
+		}
 		const effectiveType = workspace.health.healthy ? type : "warning";
 		const statusLabel = workspace.health.healthy
 			? `Workspace ${text.toLowerCase()}`