diff --git a/site/src/pages/AgentsPage/components/ChatConversation/ConversationTimeline.stories.tsx b/site/src/pages/AgentsPage/components/ChatConversation/ConversationTimeline.stories.tsx
index ead619fb7e..d086f81eb8 100644
--- a/site/src/pages/AgentsPage/components/ChatConversation/ConversationTimeline.stories.tsx
+++ b/site/src/pages/AgentsPage/components/ChatConversation/ConversationTimeline.stories.tsx
@@ -2031,14 +2031,13 @@ export const ToolDisplayModesFromPreferences: Story = {
 	},
 	play: async ({ canvasElement }) => {
 		const canvas = within(canvasElement);
-		expect(canvas.getByText("pnpm test")).toBeVisible();
+		const commandOutputButton = canvas.getByRole("button", {
+			name: "Expand command",
+		});
+		expect(commandOutputButton).toHaveTextContent("Ran pnpm test");
 		expect(canvas.queryByText("tests passed")).not.toBeInTheDocument();
 		expect(canvas.getByText(/Edited config\.ts/)).toBeVisible();
 		expect(canvas.queryAllByTestId("edit-file-diff")).toHaveLength(0);
-
-		const commandOutputButton = canvas.getByRole("button", {
-			name: "Expand command output",
-		});
 		expect(commandOutputButton).toHaveAttribute("aria-expanded", "false");
 		await userEvent.click(commandOutputButton);
 		await waitFor(() => {
diff --git a/site/src/pages/AgentsPage/components/ChatElements/tools/ExecuteTool.stories.tsx b/site/src/pages/AgentsPage/components/ChatElements/tools/ExecuteTool.stories.tsx
index 2400d856ab..bfdf822268 100644
--- a/site/src/pages/AgentsPage/components/ChatElements/tools/ExecuteTool.stories.tsx
+++ b/site/src/pages/AgentsPage/components/ChatElements/tools/ExecuteTool.stories.tsx
@@ -1,5 +1,5 @@
 import type { Meta, StoryObj } from "@storybook/react-vite";
-import { expect, screen, userEvent, within } from "storybook/test";
+import { userEvent, within } from "storybook/test";
 import { ExecuteTool } from "./ExecuteTool";
 
 const longCommand =
@@ -30,6 +30,13 @@ export const ShortCommand: Story = {
 		command: "git status",
 		output: "",
 	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		const summaryButton = await canvas.findByRole("button", {
+			name: "Expand command",
+		});
+		await userEvent.click(summaryButton);
+	},
 };
 
 export const RunningWithoutCommand: Story = {
@@ -38,31 +45,26 @@ export const RunningWithoutCommand: Story = {
 		status: "running",
 		output: "",
 	},
-	play: async ({ canvasElement }) => {
-		const canvas = within(canvasElement);
-		expect(canvas.queryByText("$")).not.toBeInTheDocument();
-		expect(
-			canvas.queryByRole("button", { name: "Copy command" }),
-		).not.toBeInTheDocument();
-	},
 };
 
 export const LongCommand: Story = {
+	decorators: [
+		(Story) => (
+			<div className="w-72">
+				<Story />
+			</div>
+		),
+	],
 	args: {
 		command: longCommand,
 		output: "",
 	},
 	play: async ({ canvasElement }) => {
 		const canvas = within(canvasElement);
-		const command = canvas.getByText(longCommand);
-		expect(command).toBeVisible();
-		expect(
-			canvas.queryByRole("button", { name: longCommand }),
-		).not.toBeInTheDocument();
-		await userEvent.hover(command);
-		expect(
-			await screen.findByRole("tooltip", undefined, { timeout: 2000 }),
-		).toHaveTextContent(longCommand);
+		const summaryButton = await canvas.findByRole("button", {
+			name: "Expand command",
+		});
+		await userEvent.click(summaryButton);
 	},
 };
 
diff --git a/site/src/pages/AgentsPage/components/ChatElements/tools/ExecuteTool.tsx b/site/src/pages/AgentsPage/components/ChatElements/tools/ExecuteTool.tsx
index 602053992c..6620a39229 100644
--- a/site/src/pages/AgentsPage/components/ChatElements/tools/ExecuteTool.tsx
+++ b/site/src/pages/AgentsPage/components/ChatElements/tools/ExecuteTool.tsx
@@ -6,7 +6,6 @@ import {
 	LayersIcon,
 	LoaderIcon,
 	OctagonXIcon,
-	TerminalIcon,
 	TriangleAlertIcon,
 } from "lucide-react";
 import type React from "react";
@@ -79,13 +78,10 @@ const ExecuteToolInner: React.FC<ExecuteToolInnerProps> = ({
 	outputInitiallyOpen,
 }) => {
 	const hasCommand = command.trim().length > 0;
-	const hasOutput = output.length > 0;
 	const isRunning = status === "running";
 	const showFailureIndicator = isError && !isRunning;
 	const [outputOpen, setOutputOpen] = useState(outputInitiallyOpen);
-	const outputToggleLabel = outputOpen
-		? "Collapse command output"
-		: "Expand command output";
+	const outputToggleLabel = outputOpen ? "Collapse command" : "Expand command";
 	const durationLabel = formatShellDurationMs(durationMs);
 
 	if (!hasCommand) {
@@ -93,36 +89,20 @@ const ExecuteToolInner: React.FC<ExecuteToolInnerProps> = ({
 	}
 
 	return (
-		<div className="group/exec grid w-full grid-cols-[minmax(0,1fr)_auto] items-start gap-x-2 rounded-md bg-surface-primary font-mono font-normal text-xs leading-5">
-			<Tooltip delayDuration={300}>
-				<TooltipTrigger asChild>
-					{hasOutput ? (
-						<button
-							type="button"
-							aria-expanded={outputOpen}
-							aria-label={outputToggleLabel}
-							onClick={() => setOutputOpen((value) => !value)}
-							className="col-start-1 row-start-1 m-0 flex w-full min-w-0 cursor-pointer items-center gap-2 border-0 bg-transparent p-0 text-left font-[inherit] font-normal text-[inherit] text-content-secondary transition-colors hover:text-content-primary"
-						>
-							<ShellCommandLine
-								command={command}
-								durationLabel={durationLabel}
-								expanded={outputOpen}
-							/>
-						</button>
-					) : (
-						<div className="col-start-1 row-start-1 flex min-w-0 items-center gap-2 font-normal text-content-secondary">
-							<ShellCommandLine
-								command={command}
-								durationLabel={durationLabel}
-							/>
-						</div>
-					)}
-				</TooltipTrigger>
-				<TooltipContent className="max-w-xl whitespace-pre-wrap break-all font-mono font-normal">
-					{command}
-				</TooltipContent>
-			</Tooltip>
+		<div className="group/exec grid w-full grid-cols-[minmax(0,1fr)_auto] items-start gap-x-2 rounded-md bg-surface-primary font-sans font-normal text-xs leading-5">
+			<button
+				type="button"
+				aria-expanded={outputOpen}
+				aria-label={outputToggleLabel}
+				onClick={() => setOutputOpen((value) => !value)}
+				className="col-start-1 row-start-1 m-0 flex w-full min-w-0 cursor-pointer items-center gap-2 border-0 bg-transparent p-0 text-left font-[inherit] font-normal text-[inherit] text-content-secondary transition-colors hover:text-content-primary"
+			>
+				<ShellCommandLine
+					command={command}
+					durationLabel={durationLabel}
+					expanded={outputOpen}
+				/>
+			</button>
 			<div className="col-start-2 row-start-1 flex shrink-0 items-center gap-1">
 				{isRunning && (
 					<LoaderIcon className="h-3.5 w-3.5 shrink-0 animate-spin motion-reduce:animate-none text-content-secondary" />
@@ -174,8 +154,12 @@ const ExecuteToolInner: React.FC<ExecuteToolInnerProps> = ({
 					className="-my-0.5 size-6 p-0 opacity-0 transition-opacity hover:bg-surface-tertiary group-hover/exec:opacity-100"
 				/>
 			</div>
-			{hasOutput && outputOpen && (
-				<ShellOutputBody output={output} isError={isError} />
+			{outputOpen && (
+				<ShellTranscriptBody
+					command={command}
+					output={output}
+					isError={isError}
+				/>
 			)}
 		</div>
 	);
@@ -188,9 +172,8 @@ const ShellCommandLine: React.FC<{
 }> = ({ command, durationLabel, expanded }) => {
 	return (
 		<>
-			<TerminalIcon aria-hidden className="size-3.5 shrink-0 text-current" />
 			<span className="block min-w-0 truncate text-[13px] font-normal text-current">
-				{command}
+				Ran {command}
 			</span>
 			{durationLabel && (
 				<span className="shrink-0 text-[13px] font-normal text-content-secondary">
@@ -209,24 +192,35 @@ const ShellCommandLine: React.FC<{
 	);
 };
 
-const ShellOutputBody: React.FC<{
+const ShellTranscriptBody: React.FC<{
+	command: string;
 	output: string;
 	isError: boolean;
-}> = ({ output, isError }) => {
+}> = ({ command, output, isError }) => {
 	return (
 		<ScrollArea
-			className="col-start-1 col-span-2 mt-1 rounded-md border border-solid border-border-default/50 bg-surface-secondary/30 text-2xs"
+			className="col-start-1 col-span-2 mt-2 rounded-xl bg-surface-secondary/60 text-2xs"
 			viewportClassName="max-h-64"
 			scrollBarClassName="w-1.5"
 		>
-			<pre
-				className={cn(
-					"m-0 whitespace-pre-wrap break-all border-0 bg-transparent px-2 py-1.5 font-mono text-xs leading-5",
-					isError ? "text-content-destructive" : "text-content-secondary",
+			<div className="px-3 py-2.5">
+				<pre className="m-0 whitespace-pre-wrap break-words border-0 bg-transparent p-0 font-mono text-xs font-semibold leading-5 text-content-primary">
+					<span aria-hidden className="select-none">
+						$
+					</span>{" "}
+					{command}
+				</pre>
+				{output.length > 0 && (
+					<pre
+						className={cn(
+							"m-0 mt-4 whitespace-pre-wrap break-words border-0 bg-transparent p-0 font-mono text-xs font-normal leading-5",
+							isError ? "text-content-destructive" : "text-content-secondary",
+						)}
+					>
+						{output}
+					</pre>
 				)}
-			>
-				{output}
-			</pre>
+			</div>
 		</ScrollArea>
 	);
 };
diff --git a/site/src/pages/AgentsPage/components/ChatElements/tools/Tool.stories.tsx b/site/src/pages/AgentsPage/components/ChatElements/tools/Tool.stories.tsx
index fc8b23793c..802d114658 100644
--- a/site/src/pages/AgentsPage/components/ChatElements/tools/Tool.stories.tsx
+++ b/site/src/pages/AgentsPage/components/ChatElements/tools/Tool.stories.tsx
@@ -99,7 +99,7 @@ export const ExecuteError: Story = {
 		expect(canvas.getByRole("img", { name: "Command failed" })).toBeVisible();
 		expect(canvas.queryByText("exit 1")).not.toBeInTheDocument();
 		await userEvent.click(
-			canvas.getByRole("button", { name: "Expand command output" }),
+			canvas.getByRole("button", { name: "Expand command" }),
 		);
 		await waitFor(() => {
 			expect(canvas.getByText(/error line 1/)).toBeVisible();
@@ -144,13 +144,16 @@ export const ExecuteAlwaysCollapsed: Story = {
 	},
 	play: async ({ canvasElement }) => {
 		const canvas = within(canvasElement);
-		expect(canvas.getByText(executeCommand)).toBeVisible();
+		const commandButton = canvas.getByRole("button", {
+			name: "Expand command",
+		});
+		expect(commandButton).toHaveTextContent(`Ran ${executeCommand}`);
 		expect(canvas.queryByText("exit 0")).not.toBeInTheDocument();
 		expect(canvas.queryByText("2 lines")).not.toBeInTheDocument();
 		expect(
 			canvas.queryByText(/From github\.com:coder\/coder/),
 		).not.toBeInTheDocument();
-		await userEvent.click(canvas.getByText(executeCommand));
+		await userEvent.click(commandButton);
 		await waitFor(() => {
 			expect(canvas.getByText(/From github\.com:coder\/coder/)).toBeVisible();
 		});
@@ -174,11 +177,11 @@ export const ExecuteLongCommandCollapsed: Story = {
 	},
 	play: async ({ canvasElement }) => {
 		const canvas = within(canvasElement);
-		const command = canvas.getByText(longExecuteCommand);
-		expect(command).toBeVisible();
-		expect(
-			canvas.queryByRole("button", { name: longExecuteCommand }),
-		).not.toBeInTheDocument();
+		const commandButton = canvas.getByRole("button", {
+			name: "Expand command",
+		});
+		expect(commandButton).toHaveTextContent(`Ran ${longExecuteCommand}`);
+		expect(commandButton).toHaveAttribute("aria-expanded", "false");
 		expect(canvas.queryByText("exit 0")).not.toBeInTheDocument();
 		expect(canvas.getByText("47.2s")).toBeVisible();
 		expect(canvas.queryByText("61 lines")).not.toBeInTheDocument();