diff --git a/site/src/pages/TaskPage/TaskAppIframe.tsx b/site/src/pages/TaskPage/TaskAppIframe.tsx
new file mode 100644
index 0000000000000..1f247bfeaab71
--- /dev/null
+++ b/site/src/pages/TaskPage/TaskAppIframe.tsx
@@ -0,0 +1,40 @@
+import type { WorkspaceApp } from "api/typesGenerated";
+import { useAppLink } from "modules/apps/useAppLink";
+import type { Task } from "modules/tasks/tasks";
+import type { FC } from "react";
+import { cn } from "utils/cn";
+
+type TaskAppIFrameProps = {
+	task: Task;
+	app: WorkspaceApp;
+	active: boolean;
+};
+
+export const TaskAppIFrame: FC<TaskAppIFrameProps> = ({
+	task,
+	app,
+	active,
+}) => {
+	const agent = task.workspace.latest_build.resources
+		.flatMap((r) => r.agents)
+		.filter((a) => !!a)
+		.find((a) => a.apps.some((a) => a.id === app.id));
+
+	if (!agent) {
+		throw new Error(`Agent for app ${app.id} not found in task workspace`);
+	}
+
+	const link = useAppLink(app, {
+		agent,
+		workspace: task.workspace,
+	});
+
+	return (
+		<iframe
+			src={link.href}
+			title={link.label}
+			loading="eager"
+			className={cn([active ? "block" : "hidden", "w-full h-full border-0"])}
+		/>
+	);
+};
diff --git a/site/src/pages/TaskPage/TaskApps.tsx b/site/src/pages/TaskPage/TaskApps.tsx
new file mode 100644
index 0000000000000..7954447853c1e
--- /dev/null
+++ b/site/src/pages/TaskPage/TaskApps.tsx
@@ -0,0 +1,169 @@
+import type { WorkspaceApp } from "api/typesGenerated";
+import { Button } from "components/Button/Button";
+import {
+	DropdownMenu,
+	DropdownMenuContent,
+	DropdownMenuItem,
+	DropdownMenuTrigger,
+} from "components/DropdownMenu/DropdownMenu";
+import { ExternalImage } from "components/ExternalImage/ExternalImage";
+import { ChevronDownIcon, LayoutGridIcon } from "lucide-react";
+import { useAppLink } from "modules/apps/useAppLink";
+import type { Task } from "modules/tasks/tasks";
+import type React from "react";
+import { type FC, useState } from "react";
+import { Link as RouterLink } from "react-router-dom";
+import { cn } from "utils/cn";
+import { TaskAppIFrame } from "./TaskAppIframe";
+import { AI_APP_CHAT_SLUG } from "./constants";
+
+type TaskAppsProps = {
+	task: Task;
+};
+
+export const TaskApps: FC<TaskAppsProps> = ({ task }) => {
+	const agents = task.workspace.latest_build.resources
+		.flatMap((r) => r.agents)
+		.filter((a) => !!a);
+
+	// The Chat UI app will be displayed in the sidebar, so we don't want to show
+	// it here
+	const apps = agents
+		.flatMap((a) => a?.apps)
+		.filter((a) => !!a && a.slug !== AI_APP_CHAT_SLUG);
+
+	const [activeAppId, setActiveAppId] = useState<string>(() => {
+		const appId = task.workspace.latest_app_status?.app_id;
+		if (!appId) {
+			throw new Error("No active app found in task");
+		}
+		return appId;
+	});
+
+	const activeApp = apps.find((app) => app.id === activeAppId);
+	if (!activeApp) {
+		throw new Error(`Active app with ID ${activeAppId} not found in task`);
+	}
+
+	const agent = agents.find((a) =>
+		a.apps.some((app) => app.id === activeAppId),
+	);
+	if (!agent) {
+		throw new Error(`Agent for app ${activeAppId} not found in task workspace`);
+	}
+
+	const embeddedApps = apps.filter((app) => !app.external);
+	const externalApps = apps.filter((app) => app.external);
+
+	return (
+		<main className="flex-1 flex flex-col">
+			<div className="border-0 border-b border-border border-solid w-full p-1 flex gap-2">
+				{embeddedApps.map((app) => (
+					<TaskAppButton
+						key={app.id}
+						task={task}
+						app={app}
+						active={app.id === activeAppId}
+						onClick={(e) => {
+							e.preventDefault();
+							setActiveAppId(app.id);
+						}}
+					/>
+				))}
+
+				{externalApps.length > 0 && (
+					<div className="ml-auto">
+						<DropdownMenu>
+							<DropdownMenuTrigger asChild>
+								<Button size="sm" variant="subtle">
+									Open locally
+									<ChevronDownIcon />
+								</Button>
+							</DropdownMenuTrigger>
+							<DropdownMenuContent>
+								{externalApps.map((app) => {
+									const link = useAppLink(app, {
+										agent,
+										workspace: task.workspace,
+									});
+
+									return (
+										<DropdownMenuItem key={app.id} asChild>
+											<RouterLink to={link.href}>
+												{app.icon ? (
+													<ExternalImage src={app.icon} />
+												) : (
+													<LayoutGridIcon />
+												)}
+												{link.label}
+											</RouterLink>
+										</DropdownMenuItem>
+									);
+								})}
+							</DropdownMenuContent>
+						</DropdownMenu>
+					</div>
+				)}
+			</div>
+
+			<div className="flex-1">
+				{embeddedApps.map((app) => {
+					return (
+						<TaskAppIFrame
+							key={app.id}
+							active={activeAppId === app.id}
+							app={app}
+							task={task}
+						/>
+					);
+				})}
+			</div>
+		</main>
+	);
+};
+
+type TaskAppButtonProps = {
+	task: Task;
+	app: WorkspaceApp;
+	active: boolean;
+	onClick: (e: React.MouseEvent<HTMLAnchorElement>) => void;
+};
+
+const TaskAppButton: FC<TaskAppButtonProps> = ({
+	task,
+	app,
+	active,
+	onClick,
+}) => {
+	const agent = task.workspace.latest_build.resources
+		.flatMap((r) => r.agents)
+		.filter((a) => !!a)
+		.find((a) => a.apps.some((a) => a.id === app.id));
+
+	if (!agent) {
+		throw new Error(`Agent for app ${app.id} not found in task workspace`);
+	}
+
+	const link = useAppLink(app, {
+		agent,
+		workspace: task.workspace,
+	});
+
+	return (
+		<Button
+			size="sm"
+			variant="subtle"
+			key={app.id}
+			asChild
+			className={cn([
+				{ "text-content-primary": active },
+				{ "opacity-75 hover:opacity-100": !active },
+			])}
+		>
+			<RouterLink to={link.href} onClick={onClick}>
+				{app.icon ? <ExternalImage src={app.icon} /> : <LayoutGridIcon />}
+				{link.label}
+			</RouterLink>
+		</Button>
+	);
+};
diff --git a/site/src/pages/TaskPage/TaskPage.tsx b/site/src/pages/TaskPage/TaskPage.tsx
index 29964ce834630..287568852d209 100644
--- a/site/src/pages/TaskPage/TaskPage.tsx
+++ b/site/src/pages/TaskPage/TaskPage.tsx
@@ -1,48 +1,20 @@
-import GitHub from "@mui/icons-material/GitHub";
 import { API } from "api/api";
 import { getErrorDetail, getErrorMessage } from "api/errors";
-import type { WorkspaceApp, WorkspaceStatus } from "api/typesGenerated";
+import type { WorkspaceStatus } from "api/typesGenerated";
 import { Button } from "components/Button/Button";
-import {
-	DropdownMenu,
-	DropdownMenuContent,
-	DropdownMenuItem,
-	DropdownMenuTrigger,
-} from "components/DropdownMenu/DropdownMenu";
-import { ExternalImage } from "components/ExternalImage/ExternalImage";
 import { Loader } from "components/Loader/Loader";
 import { Margins } from "components/Margins/Margins";
-import { ScrollArea } from "components/ScrollArea/ScrollArea";
 import { Spinner } from "components/Spinner/Spinner";
-import {
-	Tooltip,
-	TooltipContent,
-	TooltipProvider,
-	TooltipTrigger,
-} from "components/Tooltip/Tooltip";
-import {
-	ArrowLeftIcon,
-	BugIcon,
-	ChevronDownIcon,
-	EllipsisVerticalIcon,
-	ExternalLinkIcon,
-	GitPullRequestArrowIcon,
-	LayoutGridIcon,
-	RotateCcwIcon,
-} from "lucide-react";
-import { AppStatusStateIcon } from "modules/apps/AppStatusStateIcon";
-import { useAppLink } from "modules/apps/useAppLink";
+import { ArrowLeftIcon, RotateCcwIcon } from "lucide-react";
 import { AI_PROMPT_PARAMETER_NAME, type Task } from "modules/tasks/tasks";
-import type React from "react";
-import { type FC, type ReactNode, useState } from "react";
+import type { ReactNode } from "react";
 import { Helmet } from "react-helmet-async";
 import { useQuery } from "react-query";
 import { useParams } from "react-router-dom";
 import { Link as RouterLink } from "react-router-dom";
-import { cn } from "utils/cn";
 import { pageTitle } from "utils/page";
-import { timeFrom } from "utils/time";
-import { truncateURI } from "utils/uri";
+import { TaskApps } from "./TaskApps";
+import { TaskSidebar } from "./TaskSidebar";
 
 const TaskPage = () => {
 	const { workspace: workspaceName, username } = useParams() as {
@@ -204,364 +176,6 @@ const TaskPage = () => {
 
 export default TaskPage;
 
-type TaskSidebarProps = {
-	task: Task;
-};
-
-const TaskSidebar: FC<TaskSidebarProps> = ({ task }) => {
-	let statuses = task.workspace.latest_build.resources
-		.flatMap((r) => r.agents)
-		.flatMap((a) => a?.apps)
-		.flatMap((a) => a?.statuses)
-		.filter((s) => !!s)
-		.sort(
-			(a, b) =>
-				new Date(b.created_at).getTime() - new Date(a.created_at).getTime(),
-		);
-
-	// This happens when the workspace is not running so it has no resources to
-	// get the statuses so we can fallback to the latest status received from the
-	// workspace.
-	if (statuses.length === 0 && task.workspace.latest_app_status) {
-		statuses = [task.workspace.latest_app_status];
-	}
-
-	return (
-		<aside className="flex flex-col h-full border-0 border-r border-solid border-border w-[320px] shrink-0">
-			<header className="border-0 border-b border-solid border-border p-4 pt-0">
-				<div className="flex items-center justify-between py-1">
-					<TooltipProvider>
-						<Tooltip>
-							<TooltipTrigger asChild>
-								<Button size="icon" variant="subtle" asChild className="-ml-2">
-									<RouterLink to="/tasks">
-										<ArrowLeftIcon />
-										<span className="sr-only">Back to tasks</span>
-									</RouterLink>
-								</Button>
-							</TooltipTrigger>
-							<TooltipContent>Back to tasks</TooltipContent>
-						</Tooltip>
-					</TooltipProvider>
-
-					<DropdownMenu>
-						<TooltipProvider>
-							<Tooltip>
-								<TooltipTrigger asChild>
-									<DropdownMenuTrigger asChild>
-										<Button size="icon" variant="subtle" className="-mr-2">
-											<EllipsisVerticalIcon />
-											<span className="sr-only">Settings</span>
-										</Button>
-									</DropdownMenuTrigger>
-								</TooltipTrigger>
-								<TooltipContent>Settings</TooltipContent>
-							</Tooltip>
-						</TooltipProvider>
-
-						<DropdownMenuContent>
-							<DropdownMenuItem asChild>
-								<RouterLink
-									to={`/@${task.workspace.owner_name}/${task.workspace.name}`}
-								>
-									View workspace
-								</RouterLink>
-							</DropdownMenuItem>
-						</DropdownMenuContent>
-					</DropdownMenu>
-				</div>
-
-				<h1 className="m-0 mt-1 text-base font-medium">{task.prompt}</h1>
-
-				{task.workspace.latest_app_status?.uri && (
-					<div className="flex items-center gap-2 mt-2 flex-wrap">
-						<TaskStatusLink uri={task.workspace.latest_app_status.uri} />
-					</div>
-				)}
-			</header>
-
-			{statuses ? (
-				<ScrollArea className="h-full">
-					{statuses.length === 0 && (
-						<article className="px-4 py-2 flex gap-2 first-of-type:pt-4 last-of-type:pb-4">
-							<div className="flex flex-col gap-1 flex-1">
-								<h3 className="m-0 font-medium text-sm leading-normal">
-									Running your task
-								</h3>
-								<time
-									dateTime={task.workspace.latest_build.created_at}
-									className="font-medium text-xs text-content-secondary first-letter:uppercase"
-								>
-									{timeFrom(new Date(task.workspace.latest_build.created_at))}
-								</time>
-							</div>
-
-							<AppStatusStateIcon state="working" latest className="size-5" />
-						</article>
-					)}
-					{statuses.map((status, index) => {
-						return (
-							<article
-								className={cn(
-									["px-4 py-2 flex gap-2 first-of-type:pt-4 last-of-type:pb-4"],
-									{
-										"opacity-50 hover:opacity-100": index !== 0,
-									},
-								)}
-								key={status.id}
-							>
-								<div className="flex flex-col gap-1 flex-1">
-									<h3 className="m-0 font-medium text-sm leading-normal">
-										{status.message}
-									</h3>
-									<time
-										dateTime={status.created_at}
-										className="font-medium text-xs text-content-secondary first-letter:uppercase"
-									>
-										{timeFrom(new Date(status.created_at))}
-									</time>
-								</div>
-
-								<AppStatusStateIcon
-									state={status.state}
-									latest={index === 0}
-									disabled={task.workspace.latest_build.status !== "running"}
-									className={cn(["size-5", { "opacity-0": index !== 0 }])}
-								/>
-							</article>
-						);
-					})}
-				</ScrollArea>
-			) : (
-				<Spinner loading />
-			)}
-		</aside>
-	);
-};
-
-type TaskAppsProps = {
-	task: Task;
-};
-
-const TaskApps: FC<TaskAppsProps> = ({ task }) => {
-	const agents = task.workspace.latest_build.resources
-		.flatMap((r) => r.agents)
-		.filter((a) => !!a);
-
-	const apps = agents.flatMap((a) => a?.apps).filter((a) => !!a);
-
-	const [activeAppId, setActiveAppId] = useState<string>(() => {
-		const appId = task.workspace.latest_app_status?.app_id;
-		if (!appId) {
-			throw new Error("No active app found in task");
-		}
-		return appId;
-	});
-
-	const activeApp = apps.find((app) => app.id === activeAppId);
-	if (!activeApp) {
-		throw new Error(`Active app with ID ${activeAppId} not found in task`);
-	}
-
-	const agent = agents.find((a) =>
-		a.apps.some((app) => app.id === activeAppId),
-	);
-	if (!agent) {
-		throw new Error(`Agent for app ${activeAppId} not found in task workspace`);
-	}
-
-	const embeddedApps = apps.filter((app) => !app.external);
-	const externalApps = apps.filter((app) => app.external);
-
-	return (
-		<main className="flex-1 flex flex-col">
-			<div className="border-0 border-b border-border border-solid w-full p-1 flex gap-2">
-				{embeddedApps
-					.filter((app) => !app.external)
-					.map((app) => (
-						<TaskAppButton
-							key={app.id}
-							task={task}
-							app={app}
-							active={app.id === activeAppId}
-							onClick={(e) => {
-								if (app.external) {
-									return;
-								}
-
-								e.preventDefault();
-								setActiveAppId(app.id);
-							}}
-						/>
-					))}
-
-				{externalApps.length > 0 && (
-					<div className="ml-auto">
-						<DropdownMenu>
-							<DropdownMenuTrigger asChild>
-								<Button size="sm" variant="subtle">
-									Open locally
-									<ChevronDownIcon />
-								</Button>
-							</DropdownMenuTrigger>
-							<DropdownMenuContent>
-								{externalApps
-									.filter((app) => app.external)
-									.map((app) => {
-										const link = useAppLink(app, {
-											agent,
-											workspace: task.workspace,
-										});
-
-										return (
-											<DropdownMenuItem key={app.id} asChild>
-												<RouterLink to={link.href}>
-													{app.icon ? (
-														<ExternalImage src={app.icon} />
-													) : (
-														<LayoutGridIcon />
-													)}
-													{link.label}
-												</RouterLink>
-											</DropdownMenuItem>
-										);
-									})}
-							</DropdownMenuContent>
-						</DropdownMenu>
-					</div>
-				)}
-			</div>
-
-			<div className="flex-1">
-				{embeddedApps.map((app) => {
-					return (
-						<TaskAppIFrame
-							key={app.id}
-							active={activeAppId === app.id}
-							app={app}
-							task={task}
-						/>
-					);
-				})}
-			</div>
-		</main>
-	);
-};
-
-type TaskAppButtonProps = {
-	task: Task;
-	app: WorkspaceApp;
-	active: boolean;
-	onClick: (e: React.MouseEvent<HTMLAnchorElement>) => void;
-};
-
-const TaskAppButton: FC<TaskAppButtonProps> = ({
-	task,
-	app,
-	active,
-	onClick,
-}) => {
-	const agent = task.workspace.latest_build.resources
-		.flatMap((r) => r.agents)
-		.filter((a) => !!a)
-		.find((a) => a.apps.some((a) => a.id === app.id));
-
-	if (!agent) {
-		throw new Error(`Agent for app ${app.id} not found in task workspace`);
-	}
-
-	const link = useAppLink(app, {
-		agent,
-		workspace: task.workspace,
-	});
-
-	return (
-		<Button
-			size="sm"
-			variant="subtle"
-			key={app.id}
-			asChild
-			className={cn([
-				{ "text-content-primary": active },
-				{ "opacity-75 hover:opacity-100": !active },
-			])}
-		>
-			<RouterLink to={link.href} onClick={onClick}>
-				{app.icon ? <ExternalImage src={app.icon} /> : <LayoutGridIcon />}
-				{link.label}
-			</RouterLink>
-		</Button>
-	);
-};
-
-type TaskAppIFrameProps = {
-	task: Task;
-	app: WorkspaceApp;
-	active: boolean;
-};
-
-const TaskAppIFrame: FC<TaskAppIFrameProps> = ({ task, app, active }) => {
-	const agent = task.workspace.latest_build.resources
-		.flatMap((r) => r.agents)
-		.filter((a) => !!a)
-		.find((a) => a.apps.some((a) => a.id === app.id));
-
-	if (!agent) {
-		throw new Error(`Agent for app ${app.id} not found in task workspace`);
-	}
-
-	const link = useAppLink(app, {
-		agent,
-		workspace: task.workspace,
-	});
-
-	return (
-		<iframe
-			src={link.href}
-			title={link.label}
-			loading="eager"
-			className={cn([active ? "block" : "hidden", "w-full h-full border-0"])}
-		/>
-	);
-};
-
-type TaskStatusLinkProps = {
-	uri: string;
-};
-
-const TaskStatusLink: FC<TaskStatusLinkProps> = ({ uri }) => {
-	let icon = <ExternalLinkIcon />;
-	let label = truncateURI(uri);
-
-	if (uri.startsWith("https://github.com")) {
-		const issueNumber = uri.split("/").pop();
-		const [org, repo] = uri.split("/").slice(3, 5);
-		const prefix = `${org}/${repo}`;
-
-		if (uri.includes("pull/")) {
-			icon = <GitPullRequestArrowIcon />;
-			label = issueNumber
-				? `${prefix}#${issueNumber}`
-				: `${prefix} Pull Request`;
-		} else if (uri.includes("issues/")) {
-			icon = <BugIcon />;
-			label = issueNumber ? `${prefix}#${issueNumber}` : `${prefix} Issue`;
-		} else {
-			icon = <GitHub />;
-			label = `${org}/${repo}`;
-		}
-	}
-
-	return (
-		<Button asChild variant="outline" size="sm" className="min-w-0">
-			<a href={uri} target="_blank" rel="noreferrer">
-				{icon}
-				{label}
-			</a>
-		</Button>
-	);
-};
-
 export const data = {
 	fetchTask: async (workspaceOwnerUsername: string, workspaceName: string) => {
 		const workspace = await API.getWorkspaceByOwnerAndName(
diff --git a/site/src/pages/TaskPage/TaskSidebar.tsx b/site/src/pages/TaskPage/TaskSidebar.tsx
new file mode 100644
index 0000000000000..df469b796528d
--- /dev/null
+++ b/site/src/pages/TaskPage/TaskSidebar.tsx
@@ -0,0 +1,230 @@
+import GitHub from "@mui/icons-material/GitHub";
+import { Button } from "components/Button/Button";
+import {
+	DropdownMenu,
+	DropdownMenuContent,
+	DropdownMenuItem,
+	DropdownMenuTrigger,
+} from "components/DropdownMenu/DropdownMenu";
+import { ScrollArea } from "components/ScrollArea/ScrollArea";
+import { Spinner } from "components/Spinner/Spinner";
+import {
+	Tooltip,
+	TooltipContent,
+	TooltipProvider,
+	TooltipTrigger,
+} from "components/Tooltip/Tooltip";
+import {
+	ArrowLeftIcon,
+	BugIcon,
+	EllipsisVerticalIcon,
+	ExternalLinkIcon,
+	GitPullRequestArrowIcon,
+} from "lucide-react";
+import { AppStatusStateIcon } from "modules/apps/AppStatusStateIcon";
+import type { Task } from "modules/tasks/tasks";
+import type { FC } from "react";
+import { Link as RouterLink } from "react-router-dom";
+import { cn } from "utils/cn";
+import { timeFrom } from "utils/time";
+import { truncateURI } from "utils/uri";
+import { TaskAppIFrame } from "./TaskAppIframe";
+import { AI_APP_CHAT_SLUG } from "./constants";
+
+type TaskSidebarProps = {
+	task: Task;
+};
+
+export const TaskSidebar: FC<TaskSidebarProps> = ({ task }) => {
+	const chatApp = task.workspace.latest_build.resources
+		.flatMap((r) => r.agents)
+		.flatMap((a) => a?.apps)
+		.find((a) => a?.slug === AI_APP_CHAT_SLUG);
+
+	return (
+		<aside
+			className={cn([
+				[
+					"flex flex-col h-full shrink-0",
+					"border-0 border-r border-solid border-border",
+				],
+				// We want to make the sidebar wider for chat apps
+				chatApp ? "w-[440px]" : "w-[320px]",
+			])}
+		>
+			<header className="border-0 border-b border-solid border-border p-4 pt-0">
+				<div className="flex items-center justify-between py-1">
+					<TooltipProvider>
+						<Tooltip>
+							<TooltipTrigger asChild>
+								<Button size="icon" variant="subtle" asChild className="-ml-2">
+									<RouterLink to="/tasks">
+										<ArrowLeftIcon />
+										<span className="sr-only">Back to tasks</span>
+									</RouterLink>
+								</Button>
+							</TooltipTrigger>
+							<TooltipContent>Back to tasks</TooltipContent>
+						</Tooltip>
+					</TooltipProvider>
+
+					<DropdownMenu>
+						<TooltipProvider>
+							<Tooltip>
+								<TooltipTrigger asChild>
+									<DropdownMenuTrigger asChild>
+										<Button size="icon" variant="subtle" className="-mr-2">
+											<EllipsisVerticalIcon />
+											<span className="sr-only">Settings</span>
+										</Button>
+									</DropdownMenuTrigger>
+								</TooltipTrigger>
+								<TooltipContent>Settings</TooltipContent>
+							</Tooltip>
+						</TooltipProvider>
+
+						<DropdownMenuContent>
+							<DropdownMenuItem asChild>
+								<RouterLink
+									to={`/@${task.workspace.owner_name}/${task.workspace.name}`}
+								>
+									View workspace
+								</RouterLink>
+							</DropdownMenuItem>
+						</DropdownMenuContent>
+					</DropdownMenu>
+				</div>
+
+				<h1 className="m-0 mt-1 text-base font-medium">{task.prompt}</h1>
+
+				{task.workspace.latest_app_status?.uri && (
+					<div className="flex items-center gap-2 mt-2 flex-wrap">
+						<TaskStatusLink uri={task.workspace.latest_app_status.uri} />
+					</div>
+				)}
+			</header>
+
+			{chatApp ? (
+				<TaskAppIFrame active key={chatApp.id} app={chatApp} task={task} />
+			) : (
+				<TaskStatuses task={task} />
+			)}
+		</aside>
+	);
+};
+
+type TaskStatusesProps = {
+	task: Task;
+};
+
+const TaskStatuses: FC<TaskStatusesProps> = ({ task }) => {
+	let statuses = task.workspace.latest_build.resources
+		.flatMap((r) => r.agents)
+		.flatMap((a) => a?.apps)
+		.flatMap((a) => a?.statuses)
+		.filter((s) => !!s)
+		.sort(
+			(a, b) =>
+				new Date(b.created_at).getTime() - new Date(a.created_at).getTime(),
+		);
+
+	// This happens when the workspace is not running so it has no resources to
+	// get the statuses so we can fallback to the latest status received from the
+	// workspace.
+	if (statuses.length === 0 && task.workspace.latest_app_status) {
+		statuses = [task.workspace.latest_app_status];
+	}
+
+	return statuses ? (
+		<ScrollArea className="h-full">
+			{statuses.length === 0 && (
+				<article className="px-4 py-2 flex gap-2 first-of-type:pt-4 last-of-type:pb-4">
+					<div className="flex flex-col gap-1 flex-1">
+						<h3 className="m-0 font-medium text-sm leading-normal">
+							Running your task
+						</h3>
+						<time
+							dateTime={task.workspace.latest_build.created_at}
+							className="font-medium text-xs text-content-secondary first-letter:uppercase"
+						>
+							{timeFrom(new Date(task.workspace.latest_build.created_at))}
+						</time>
+					</div>
+
+					<AppStatusStateIcon state="working" latest className="size-5" />
+				</article>
+			)}
+			{statuses.map((status, index) => {
+				return (
+					<article
+						className={cn(
+							["px-4 py-2 flex gap-2 first-of-type:pt-4 last-of-type:pb-4"],
+							{
+								"opacity-50 hover:opacity-100": index !== 0,
+							},
+						)}
+						key={status.id}
+					>
+						<div className="flex flex-col gap-1 flex-1">
+							<h3 className="m-0 font-medium text-sm leading-normal">
+								{status.message}
+							</h3>
+							<time
+								dateTime={status.created_at}
+								className="font-medium text-xs text-content-secondary first-letter:uppercase"
+							>
+								{timeFrom(new Date(status.created_at))}
+							</time>
+						</div>
+
+						<AppStatusStateIcon
+							state={status.state}
+							latest={index === 0}
+							disabled={task.workspace.latest_build.status !== "running"}
+							className={cn(["size-5", { "opacity-0": index !== 0 }])}
+						/>
+					</article>
+				);
+			})}
+		</ScrollArea>
+	) : (
+		<Spinner loading />
+	);
+};
+
+type TaskStatusLinkProps = {
+	uri: string;
+};
+
+const TaskStatusLink: FC<TaskStatusLinkProps> = ({ uri }) => {
+	let icon = <ExternalLinkIcon />;
+	let label = truncateURI(uri);
+
+	if (uri.startsWith("https://github.com")) {
+		const issueNumber = uri.split("/").pop();
+		const [org, repo] = uri.split("/").slice(3, 5);
+		const prefix = `${org}/${repo}`;
+
+		if (uri.includes("pull/")) {
+			icon = <GitPullRequestArrowIcon />;
+			label = issueNumber
+				? `${prefix}#${issueNumber}`
+				: `${prefix} Pull Request`;
+		} else if (uri.includes("issues/")) {
+			icon = <BugIcon />;
+			label = issueNumber ? `${prefix}#${issueNumber}` : `${prefix} Issue`;
+		} else {
+			icon = <GitHub />;
+			label = `${org}/${repo}`;
+		}
+	}
+
+	return (
+		<Button asChild variant="outline" size="sm" className="min-w-0">
+			<a href={uri} target="_blank" rel="noreferrer">
+				{icon}
+				{label}
+			</a>
+		</Button>
+	);
+};
diff --git a/site/src/pages/TaskPage/constants.ts b/site/src/pages/TaskPage/constants.ts
new file mode 100644
index 0000000000000..a7a24f21ff411
--- /dev/null
+++ b/site/src/pages/TaskPage/constants.ts
@@ -0,0 +1 @@
+export const AI_APP_CHAT_SLUG = "claude-code-web";