diff --git a/site/src/modules/resources/AgentRow.tsx b/site/src/modules/resources/AgentRow.tsx
index 19fabffe3f..ea78e5d6ad 100644
--- a/site/src/modules/resources/AgentRow.tsx
+++ b/site/src/modules/resources/AgentRow.tsx
@@ -5,6 +5,7 @@ import {
 	EllipsisIcon,
 	PlayIcon,
 	SquareCheckBigIcon,
+	TriangleAlertIcon,
 } from "lucide-react";
 import {
 	type FC,
@@ -25,6 +26,7 @@ import type {
 } from "#/api/typesGenerated";
 import { CheckIcon } from "#/components/AnimatedIcons/Check";
 import { ChevronDownIcon } from "#/components/AnimatedIcons/ChevronDown";
+import { Badge } from "#/components/Badge/Badge";
 import { Button } from "#/components/Button/Button";
 import {
 	DropdownMenu,
@@ -45,6 +47,8 @@ import { useKebabMenu } from "#/components/Tabs/utils/useKebabMenu";
 import { useProxy } from "#/contexts/ProxyContext";
 import { useClipboard } from "#/hooks/useClipboard";
 import { useFeatureVisibility } from "#/modules/dashboard/useFeatureVisibility";
+import { getAgentHealthIssues } from "#/modules/workspaces/health";
+import { AgentAlert } from "#/pages/WorkspacePage/AgentAlert";
 import { AppStatuses } from "#/pages/WorkspacePage/AppStatuses";
 import { cn } from "#/utils/cn";
 import { AgentApps, organizeAgentApps } from "./AgentApps/AgentApps";
@@ -135,9 +139,12 @@ export const AgentRow: FC<AgentRowProps> = ({
 	const showVSCode = hasVSCodeApp && !browser_only;
 
 	const hasStartupFeatures = Boolean(agent.logs_length);
+	const healthIssues = getAgentHealthIssues(agent);
+	const hasAgentIssues = healthIssues.length > 0;
 	const { proxy } = useProxy();
 	const [showLogs, setShowLogs] = useState(
-		["starting", "start_timeout"].includes(agent.lifecycle_state) &&
+		(["starting", "start_timeout"].includes(agent.lifecycle_state) ||
+			hasAgentIssues) &&
 			hasStartupFeatures,
 	);
 	const agentLogs = useAgentLogs({ agentId: agent.id, enabled: showLogs });
@@ -146,8 +153,11 @@ export const AgentRow: FC<AgentRowProps> = ({
 	const [bottomOfLogs, setBottomOfLogs] = useState(true);
 
 	useEffect(() => {
-		setShowLogs(agent.lifecycle_state !== "ready" && hasStartupFeatures);
-	}, [agent.lifecycle_state, hasStartupFeatures]);
+		setShowLogs(
+			(agent.lifecycle_state !== "ready" || hasAgentIssues) &&
+				hasStartupFeatures,
+		);
+	}, [agent.lifecycle_state, hasAgentIssues, hasStartupFeatures]);
 
 	// This is a layout effect to remove flicker when we're scrolling to the bottom.
 	// biome-ignore lint/correctness/useExhaustiveDependencies: consider refactoring
@@ -208,7 +218,6 @@ export const AgentRow: FC<AgentRowProps> = ({
 		agent,
 		Boolean(hasDevcontainerErrors || shouldShowWildcardWarning),
 	);
-
 	const [selectedLogTab, setSelectedLogTab] = useState("all");
 	const sourceLogTabs = agent.log_sources
 		.filter((logSource) => {
@@ -459,20 +468,37 @@ export const AgentRow: FC<AgentRowProps> = ({
 				<AgentMetadata initialMetadata={initialMetadata} agent={agent} />
 			</div>
 
-			{hasStartupFeatures && (
-				<section className="border-0 border-t border-solid border-border">
-					<div className="px-4 py-2 relative">
-						<Button
-							variant="subtle"
-							onClick={() => setShowLogs((v) => !v)}
-							className="after:content-[''] after:absolute after:inset-0"
-						>
-							<ChevronDownIcon open={showLogs} />
-							<span>Logs</span>
-						</Button>
-					</div>
-					<Collapse in={showLogs}>
-						<div className="px-4 pb-4">
+			<section className="border-0 border-t border-solid border-border">
+				<div className="px-4 py-2 relative">
+					<Button
+						variant="subtle"
+						onClick={() => setShowLogs((v) => !v)}
+						className="after:content-[''] after:absolute after:inset-0"
+					>
+						<ChevronDownIcon open={showLogs} />
+						<span>Logs</span>
+						{healthIssues.length > 0 && (
+							<Badge variant="warning" size="xs" className="ml-1.5">
+								<TriangleAlertIcon />
+								<span>{healthIssues.length}</span>
+							</Badge>
+						)}
+					</Button>
+				</div>
+				<Collapse in={showLogs || (!hasStartupFeatures && hasAgentIssues)}>
+					<div className={cn("px-4", hasStartupFeatures ? "pb-4" : "py-4")}>
+						{healthIssues.length > 0 && (
+							<div className="mb-4 flex flex-col gap-3">
+								{healthIssues.map((issue) => (
+									<AgentAlert
+										key={`${issue.title}-${issue.detail}`}
+										{...issue}
+										troubleshootingURL={agent.troubleshooting_url}
+									/>
+								))}
+							</div>
+						)}
+						{hasStartupFeatures && hasAnyLogs && (
 							<div className="border border-solid rounded-md overflow-clip">
 								<Tabs
 									className="-mx-px -mt-px"
@@ -585,10 +611,10 @@ export const AgentRow: FC<AgentRowProps> = ({
 									</TabsContent>
 								</Tabs>
 							</div>
-						</div>
-					</Collapse>
-				</section>
-			)}
+						)}
+					</div>
+				</Collapse>
+			</section>
 		</div>
 	);
 };
diff --git a/site/src/modules/workspaces/WorkspaceStatusIndicator/WorkspaceStatusIndicator.tsx b/site/src/modules/workspaces/WorkspaceStatusIndicator/WorkspaceStatusIndicator.tsx
index 0885253833..186296c514 100644
--- a/site/src/modules/workspaces/WorkspaceStatusIndicator/WorkspaceStatusIndicator.tsx
+++ b/site/src/modules/workspaces/WorkspaceStatusIndicator/WorkspaceStatusIndicator.tsx
@@ -11,7 +11,6 @@ import {
 	TooltipContent,
 	TooltipTrigger,
 } from "#/components/Tooltip/Tooltip";
-import { getAgentHealthIssue } from "#/modules/workspaces/health";
 import {
 	type DisplayWorkspaceStatusType,
 	getDisplayWorkspaceStatus,
@@ -68,7 +67,10 @@ export const WorkspaceStatusIndicator: FC<WorkspaceStatusIndicatorProps> = ({
 					{children}
 				</StatusIndicator>
 			</TooltipTrigger>
-			<TooltipContent>{getAgentHealthIssue(workspace).detail}</TooltipContent>
+			<TooltipContent>
+				One or more workspace agents need attention. Expand an agent's logs for
+				details.
+			</TooltipContent>
 		</Tooltip>
 	);
 };
diff --git a/site/src/modules/workspaces/health.test.ts b/site/src/modules/workspaces/health.test.ts
index 357a6ccadb..8800cb8791 100644
--- a/site/src/modules/workspaces/health.test.ts
+++ b/site/src/modules/workspaces/health.test.ts
@@ -1,16 +1,11 @@
 import { describe, expect, it } from "vitest";
 import type {
-	Workspace,
+	WorkspaceAgent,
 	WorkspaceAgentLifecycle,
 	WorkspaceAgentStatus,
 } from "#/api/typesGenerated";
-import {
-	MockWorkspace,
-	MockWorkspaceAgent,
-	MockWorkspaceBuild,
-	MockWorkspaceResource,
-} from "#/testHelpers/entities";
-import { getAgentHealthIssue } from "./health";
+import { MockWorkspaceAgent } from "#/testHelpers/entities";
+import { getAgentHealthIssues } from "./health";
 
 interface AgentOverrides {
 	status?: WorkspaceAgentStatus;
@@ -18,375 +13,119 @@ interface AgentOverrides {
 	parent_id?: string | null;
 }
 
-/**
- * Build a workspace mock with the given agent configurations and
- * failing-agent count. Defaults to status "connected" and lifecycle
- * "ready" so each test only needs to specify the fields it cares about.
- */
-function buildWorkspace(
-	agents: AgentOverrides[],
-	failingAgentCount: number,
-): Workspace {
+function buildAgent(overrides: AgentOverrides): WorkspaceAgent {
 	return {
-		...MockWorkspace,
-		latest_build: {
-			...MockWorkspaceBuild,
-			resources: [
-				{
-					...MockWorkspaceResource,
-					agents: agents.map((overrides, i) => ({
-						...MockWorkspaceAgent,
-						id: `agent-${i}`,
-						name: `agent-${i}`,
-						status: overrides.status ?? "connected",
-						lifecycle_state: overrides.lifecycle_state ?? "ready",
-						parent_id: overrides.parent_id ?? null,
-					})),
-				},
-			],
-		},
-		health: {
-			healthy: failingAgentCount === 0,
-			failing_agents: Array.from(
-				{ length: failingAgentCount },
-				(_, i) => `agent-${i}`,
-			),
-		},
+		...MockWorkspaceAgent,
+		status: overrides.status ?? "connected",
+		lifecycle_state: overrides.lifecycle_state ?? "ready",
+		parent_id: overrides.parent_id ?? null,
 	};
 }
 
-describe("getAgentHealthIssue", () => {
-	describe("individual branches", () => {
-		it("returns disconnected issue for a disconnected agent", () => {
-			const ws = buildWorkspace(
-				[{ status: "disconnected", lifecycle_state: "ready" }],
-				1,
-			);
-			expect(getAgentHealthIssue(ws)).toEqual({
+describe("getAgentHealthIssues", () => {
+	it("returns disconnected issue for a disconnected agent", () => {
+		expect(
+			getAgentHealthIssues(buildAgent({ status: "disconnected" })),
+		).toContainEqual(
+			expect.objectContaining({
 				title: "Workspace agent has disconnected",
-				detail:
-					"Check the log output for errors. If agents do not reconnect, try restarting the workspace.",
 				severity: "warning",
-				prominent: true,
-			});
-		});
+				prominent: false,
+			}),
+		);
+	});
 
-		it("returns timeout issue for a timed-out agent", () => {
-			const ws = buildWorkspace(
-				[{ status: "timeout", lifecycle_state: "ready" }],
-				1,
-			);
-			expect(getAgentHealthIssue(ws)).toEqual({
+	it("returns timeout issue for a timed-out agent", () => {
+		expect(
+			getAgentHealthIssues(buildAgent({ status: "timeout" })),
+		).toContainEqual(
+			expect.objectContaining({
 				title: "Agent is taking longer than expected to connect",
-				detail:
-					"Continue to wait and check the log output for errors. If agents do not connect, try restarting the workspace.",
 				severity: "warning",
 				prominent: false,
-			});
-		});
+			}),
+		);
+	});
 
-		it("returns shutting down issue for shutting_down lifecycle", () => {
-			const ws = buildWorkspace(
-				[{ status: "connected", lifecycle_state: "shutting_down" }],
-				1,
-			);
-			expect(getAgentHealthIssue(ws)).toEqual({
+	it("returns shutdown issue for shutdown lifecycle states", () => {
+		expect(
+			getAgentHealthIssues(buildAgent({ lifecycle_state: "shutting_down" })),
+		).toContainEqual(
+			expect.objectContaining({
 				title: "Workspace agent is shutting down",
-				detail: "The workspace is not available while agents shut down.",
 				severity: "info",
-				prominent: false,
-			});
-		});
-
-		it("returns shutting down issue for shutdown_error lifecycle", () => {
-			const ws = buildWorkspace(
-				[{ status: "connected", lifecycle_state: "shutdown_error" }],
-				1,
-			);
-			expect(getAgentHealthIssue(ws)).toEqual({
+			}),
+		);
+		expect(
+			getAgentHealthIssues(buildAgent({ lifecycle_state: "shutdown_error" })),
+		).toContainEqual(
+			expect.objectContaining({
 				title: "Workspace agent is shutting down",
-				detail: "The workspace is not available while agents shut down.",
 				severity: "info",
-				prominent: false,
-			});
-		});
-
-		it("returns shutting down issue for shutdown_timeout lifecycle", () => {
-			const ws = buildWorkspace(
-				[{ status: "connected", lifecycle_state: "shutdown_timeout" }],
-				1,
-			);
-			expect(getAgentHealthIssue(ws)).toEqual({
+			}),
+		);
+		expect(
+			getAgentHealthIssues(buildAgent({ lifecycle_state: "shutdown_timeout" })),
+		).toContainEqual(
+			expect.objectContaining({
 				title: "Workspace agent is shutting down",
-				detail: "The workspace is not available while agents shut down.",
 				severity: "info",
-				prominent: false,
-			});
-		});
+			}),
+		);
+	});
 
-		it("returns start error issue for start_error lifecycle", () => {
-			const ws = buildWorkspace(
-				[{ status: "connected", lifecycle_state: "start_error" }],
-				1,
-			);
-			expect(getAgentHealthIssue(ws)).toEqual({
+	it("returns startup script issues", () => {
+		expect(
+			getAgentHealthIssues(buildAgent({ lifecycle_state: "start_error" })),
+		).toContainEqual(
+			expect.objectContaining({
 				title: "Startup script failed",
-				detail:
-					"A startup script exited with an error. Check the agent logs for details.",
-				severity: "warning",
-				prominent: true,
-			});
-		});
-
-		it("returns start timeout issue for start_timeout lifecycle", () => {
-			const ws = buildWorkspace(
-				[{ status: "connected", lifecycle_state: "start_timeout" }],
-				1,
-			);
-			expect(getAgentHealthIssue(ws)).toEqual({
-				title: "Startup script is taking longer than expected",
-				detail:
-					"A startup script has exceeded the expected time. Check the agent logs for details.",
 				severity: "warning",
 				prominent: false,
-			});
-		});
+			}),
+		);
+		expect(
+			getAgentHealthIssues(buildAgent({ lifecycle_state: "start_timeout" })),
+		).toContainEqual(
+			expect.objectContaining({
+				title: "Startup script is taking longer than expected",
+				severity: "warning",
+				prominent: false,
+			}),
+		);
+	});
 
-		it("returns connecting issue for a connecting agent", () => {
-			const ws = buildWorkspace(
-				[{ status: "connecting", lifecycle_state: "starting" }],
-				1,
-			);
-			expect(getAgentHealthIssue(ws)).toEqual({
+	it("returns connecting issue for a connecting agent", () => {
+		expect(
+			getAgentHealthIssues(
+				buildAgent({ status: "connecting", lifecycle_state: "starting" }),
+			),
+		).toContainEqual(
+			expect.objectContaining({
 				title: "Workspace agent is connecting",
-				detail:
-					"The workspace agent has not connected yet. Wait for it to connect or check the logs if it does not.",
 				severity: "info",
 				prominent: false,
-			});
-		});
+			}),
+		);
 	});
 
-	describe("plural path", () => {
-		it("uses plural title when multiple agents are disconnected", () => {
-			const ws = buildWorkspace(
-				[
-					{ status: "disconnected", lifecycle_state: "ready" },
-					{ status: "disconnected", lifecycle_state: "ready" },
-					{ status: "disconnected", lifecycle_state: "ready" },
-				],
-				3,
-			);
-			const result = getAgentHealthIssue(ws);
-			expect(result.title).toBe("3 workspace agents have disconnected");
-		});
-
-		it("uses plural title when multiple agents time out", () => {
-			const ws = buildWorkspace(
-				[
-					{ status: "timeout", lifecycle_state: "ready" },
-					{ status: "timeout", lifecycle_state: "ready" },
-				],
-				2,
-			);
-			const result = getAgentHealthIssue(ws);
-			expect(result.title).toBe(
-				"2 agents are taking longer than expected to connect",
-			);
-		});
-
-		it("uses plural title when multiple agents have start errors", () => {
-			const ws = buildWorkspace(
-				[
-					{ status: "connected", lifecycle_state: "start_error" },
-					{ status: "connected", lifecycle_state: "start_error" },
-				],
-				2,
-			);
-			const result = getAgentHealthIssue(ws);
-			expect(result.title).toBe("Startup scripts failed on 2 agents");
-		});
-
-		it("uses plural title when multiple agents are shutting down", () => {
-			const ws = buildWorkspace(
-				[
-					{ status: "connected", lifecycle_state: "shutting_down" },
-					{ status: "connected", lifecycle_state: "shutdown_error" },
-				],
-				2,
-			);
-			const result = getAgentHealthIssue(ws);
-			expect(result.title).toBe("2 workspace agents are shutting down");
-		});
-
-		it("uses plural title when multiple agents are connecting", () => {
-			const ws = buildWorkspace(
-				[
-					{ status: "connecting", lifecycle_state: "starting" },
-					{ status: "connecting", lifecycle_state: "starting" },
-				],
-				2,
-			);
-			const result = getAgentHealthIssue(ws);
-			expect(result.title).toBe("2 workspace agents are connecting");
-		});
-
-		it("uses singular title when only one agent is failing", () => {
-			const ws = buildWorkspace(
-				[{ status: "disconnected", lifecycle_state: "ready" }],
-				1,
-			);
-			const result = getAgentHealthIssue(ws);
-			expect(result.title).toBe("Workspace agent has disconnected");
-		});
+	it("returns empty list for healthy ready connected agent", () => {
+		expect(
+			getAgentHealthIssues(
+				buildAgent({ status: "connected", lifecycle_state: "ready" }),
+			),
+		).toEqual([]);
 	});
 
-	describe("priority ordering", () => {
-		it("disconnected takes priority over timeout", () => {
-			const ws = buildWorkspace(
-				[
-					{ status: "disconnected", lifecycle_state: "ready" },
-					{ status: "timeout", lifecycle_state: "ready" },
-				],
-				2,
-			);
-			const result = getAgentHealthIssue(ws);
-			expect(result.title).toBe("2 workspace agents have disconnected");
-			expect(result.severity).toBe("warning");
-			expect(result.prominent).toBe(true);
-		});
-
-		it("timeout takes priority over shutdown states", () => {
-			const ws = buildWorkspace(
-				[
-					{ status: "timeout", lifecycle_state: "ready" },
-					{ status: "connected", lifecycle_state: "shutting_down" },
-				],
-				2,
-			);
-			const result = getAgentHealthIssue(ws);
-			expect(result.title).toBe(
-				"2 agents are taking longer than expected to connect",
-			);
-			expect(result.severity).toBe("warning");
-			expect(result.prominent).toBe(false);
-		});
-
-		it("shutdown states take priority over start_error", () => {
-			const ws = buildWorkspace(
-				[
-					{ status: "connected", lifecycle_state: "shutting_down" },
-					{ status: "connected", lifecycle_state: "start_error" },
-				],
-				2,
-			);
-			const result = getAgentHealthIssue(ws);
-			expect(result.title).toBe("2 workspace agents are shutting down");
-			expect(result.severity).toBe("info");
-		});
-
-		it("start_error takes priority over start_timeout", () => {
-			const ws = buildWorkspace(
-				[
-					{ status: "connected", lifecycle_state: "start_error" },
-					{ status: "connected", lifecycle_state: "start_timeout" },
-				],
-				2,
-			);
-			const result = getAgentHealthIssue(ws);
-			expect(result.title).toBe("Startup scripts failed on 2 agents");
-			expect(result.severity).toBe("warning");
-			expect(result.prominent).toBe(true);
-		});
-
-		it("disconnected takes priority over all lifecycle states", () => {
-			const ws = buildWorkspace(
-				[
-					{ status: "disconnected", lifecycle_state: "start_error" },
-					{ status: "connected", lifecycle_state: "shutting_down" },
-					{ status: "connected", lifecycle_state: "start_timeout" },
-				],
-				3,
-			);
-			const result = getAgentHealthIssue(ws);
-			expect(result.title).toBe("3 workspace agents have disconnected");
-		});
-	});
-
-	describe("sub-agent filtering", () => {
-		it("ignores a sub-agent whose status would change the result", () => {
-			const ws = buildWorkspace(
-				[
-					// Parent agent: still connecting.
-					{ status: "connecting", lifecycle_state: "starting" },
-					// Sub-agent: disconnected, which would be highest priority
-					// if not filtered out.
-					{
-						status: "disconnected",
-						lifecycle_state: "ready",
-						parent_id: "agent-0",
-					},
-				],
-				1,
-			);
-			const result = getAgentHealthIssue(ws);
-			expect(result.title).toBe("Workspace agent is connecting");
-			expect(result.severity).toBe("info");
-		});
-
-		it("ignores a sub-agent whose lifecycle would promote severity", () => {
-			const ws = buildWorkspace(
-				[
-					// Parent agent: soft start_timeout issue.
-					{ status: "connected", lifecycle_state: "start_timeout" },
-					// Sub-agent: start_error, which would take priority over
-					// start_timeout if not filtered.
-					{
-						status: "connected",
-						lifecycle_state: "start_error",
-						parent_id: "agent-0",
-					},
-				],
-				1,
-			);
-			const result = getAgentHealthIssue(ws);
-			expect(result.title).toBe(
-				"Startup script is taking longer than expected",
-			);
-			expect(result.prominent).toBe(false);
-		});
-	});
-
-	describe("start_timeout reachability", () => {
-		it("is overshadowed by start_error in a multi-agent workspace", () => {
-			const ws = buildWorkspace(
-				[
-					{ status: "connected", lifecycle_state: "start_timeout" },
-					{ status: "connected", lifecycle_state: "start_error" },
-				],
-				2,
-			);
-			const result = getAgentHealthIssue(ws);
-			expect(result.title).toBe("Startup scripts failed on 2 agents");
-			expect(result.prominent).toBe(true);
-		});
-
-		it("is returned when it is the sole lifecycle issue", () => {
-			// In a multi-agent workspace another agent may have triggered
-			// the unhealthy flag while this agent only has start_timeout.
-			const ws = buildWorkspace(
-				[
-					{ status: "connected", lifecycle_state: "start_timeout" },
-					{ status: "connected", lifecycle_state: "ready" },
-				],
-				1,
-			);
-			const result = getAgentHealthIssue(ws);
-			expect(result.title).toBe(
-				"Startup script is taking longer than expected",
-			);
-			expect(result.severity).toBe("warning");
-			expect(result.prominent).toBe(false);
-		});
+	it("returns multiple issues when multiple conditions match", () => {
+		const issues = getAgentHealthIssues(
+			buildAgent({ status: "disconnected", lifecycle_state: "start_error" }),
+		);
+		expect(issues).toContainEqual(
+			expect.objectContaining({ title: "Workspace agent has disconnected" }),
+		);
+		expect(issues).toContainEqual(
+			expect.objectContaining({ title: "Startup script failed" }),
+		);
 	});
 });
diff --git a/site/src/modules/workspaces/health.ts b/site/src/modules/workspaces/health.ts
index 88d8ff43b7..e1faa72597 100644
--- a/site/src/modules/workspaces/health.ts
+++ b/site/src/modules/workspaces/health.ts
@@ -1,10 +1,10 @@
-import type { Workspace, WorkspaceAgentStatus } from "#/api/typesGenerated";
+import type { WorkspaceAgent } from "#/api/typesGenerated";
 
 /**
  * Canonical messages for startup and shutdown script issues.
  * Used by the per-agent-row tooltips in AgentStatus; the
- * start-related entries are also shared with the workspace-level
- * health classification in getAgentHealthIssue.
+ * start-related entries are also shared with per-agent health
+ * classification in getAgentHealthIssues.
  */
 export const agentScriptMessages = {
 	start_error: {
@@ -62,121 +62,70 @@ interface AgentHealthIssue {
 }
 
 /**
- * Classifies the health issue affecting a workspace based on agent
- * status and lifecycle state. Returns a title and detail message
- * that accurately describes the root cause rather than using a
- * generic "unhealthy" label.
+ * Classifies all health issues for an individual agent.
  */
-export function getAgentHealthIssue(workspace: Workspace): AgentHealthIssue {
-	const failingAgentCount = workspace.health.failing_agents.length;
-	const statusSet = new Set<WorkspaceAgentStatus>();
-	let hasStartError = false;
-	let hasStartTimeout = false;
-	let hasShutdownState = false;
+export function getAgentHealthIssues(
+	agent: WorkspaceAgent,
+): AgentHealthIssue[] {
+	const issues: AgentHealthIssue[] = [];
 
-	for (const resource of workspace.latest_build.resources) {
-		for (const agent of resource.agents ?? []) {
-			// Skip sub-agents (devcontainer agents) to match the
-			// backend health calculation which excludes them.
-			if (agent.parent_id !== null) {
-				continue;
-			}
-			statusSet.add(agent.status);
-			if (agent.lifecycle_state === "start_error") {
-				hasStartError = true;
-			}
-			if (agent.lifecycle_state === "start_timeout") {
-				hasStartTimeout = true;
-			}
-			if (
-				agent.lifecycle_state === "shutting_down" ||
-				agent.lifecycle_state === "shutdown_error" ||
-				agent.lifecycle_state === "shutdown_timeout"
-			) {
-				hasShutdownState = true;
-			}
-		}
-	}
-
-	const plural = failingAgentCount > 1;
-
-	if (statusSet.has("disconnected")) {
-		return {
-			title: plural
-				? `${failingAgentCount} workspace agents have disconnected`
-				: agentConnectionMessages.disconnected.title,
+	if (agent.status === "disconnected") {
+		issues.push({
+			title: agentConnectionMessages.disconnected.title,
 			detail: agentConnectionMessages.disconnected.detail,
 			severity: "warning",
-			prominent: true,
-		};
+			prominent: false,
+		});
 	}
 
-	if (statusSet.has("timeout")) {
-		return {
-			title: plural
-				? `${failingAgentCount} agents are taking longer than expected to connect`
-				: agentConnectionMessages.timeout.title,
+	if (agent.status === "timeout") {
+		issues.push({
+			title: agentConnectionMessages.timeout.title,
 			detail: agentConnectionMessages.timeout.detail,
 			severity: "warning",
 			prominent: false,
-		};
+		});
 	}
 
-	if (hasShutdownState) {
-		return {
-			title: plural
-				? `${failingAgentCount} workspace agents are shutting down`
-				: "Workspace agent is shutting down",
+	if (
+		agent.lifecycle_state === "shutting_down" ||
+		agent.lifecycle_state === "shutdown_error" ||
+		agent.lifecycle_state === "shutdown_timeout"
+	) {
+		issues.push({
+			title: "Workspace agent is shutting down",
 			detail: "The workspace is not available while agents shut down.",
 			severity: "info",
 			prominent: false,
-		};
+		});
 	}
 
-	if (hasStartError) {
-		return {
-			title: plural
-				? `Startup scripts failed on ${failingAgentCount} agents`
-				: agentScriptMessages.start_error.title,
+	if (agent.lifecycle_state === "start_error") {
+		issues.push({
+			title: agentScriptMessages.start_error.title,
 			detail: agentScriptMessages.start_error.detail,
 			severity: "warning",
-			prominent: true,
-		};
+			prominent: false,
+		});
 	}
 
-	// The backend does not mark start_timeout agents as unhealthy on
-	// their own (it treats it as a soft issue). This branch is only
-	// reachable in multi-agent workspaces where a different agent
-	// triggered the unhealthy flag but none of the higher-priority
-	// branches matched.
-	if (hasStartTimeout) {
-		return {
-			title: plural
-				? `Startup scripts are taking longer than expected on ${failingAgentCount} agents`
-				: agentScriptMessages.start_timeout.title,
+	if (agent.lifecycle_state === "start_timeout") {
+		issues.push({
+			title: agentScriptMessages.start_timeout.title,
 			detail: agentScriptMessages.start_timeout.detail,
 			severity: "warning",
 			prominent: false,
-		};
+		});
 	}
 
-	if (statusSet.has("connecting")) {
-		return {
-			title: plural
-				? `${failingAgentCount} workspace agents are connecting`
-				: agentConnectionMessages.connecting.title,
+	if (agent.status === "connecting") {
+		issues.push({
+			title: agentConnectionMessages.connecting.title,
 			detail: agentConnectionMessages.connecting.detail,
 			severity: "info",
 			prominent: false,
-		};
+		});
 	}
 
-	return {
-		title: plural
-			? `${failingAgentCount} workspace agents are still connecting`
-			: "Workspace agent is still connecting",
-		detail: "Check the log output if the connection does not complete.",
-		severity: "info",
-		prominent: false,
-	};
+	return issues;
 }
diff --git a/site/src/pages/WorkspacePage/WorkspaceAlert.stories.tsx b/site/src/pages/WorkspacePage/AgentAlert.stories.tsx
similarity index 79%
rename from site/src/pages/WorkspacePage/WorkspaceAlert.stories.tsx
rename to site/src/pages/WorkspacePage/AgentAlert.stories.tsx
index 4ca68e98e6..464e7cb8ab 100644
--- a/site/src/pages/WorkspacePage/WorkspaceAlert.stories.tsx
+++ b/site/src/pages/WorkspacePage/AgentAlert.stories.tsx
@@ -1,9 +1,9 @@
 import type { Meta, StoryObj } from "@storybook/react-vite";
-import { WorkspaceAlert } from "./WorkspaceAlert";
+import { AgentAlert } from "./AgentAlert";
 
-const meta: Meta<typeof WorkspaceAlert> = {
-	title: "pages/WorkspacePage/WorkspaceAlert",
-	component: WorkspaceAlert,
+const meta: Meta<typeof AgentAlert> = {
+	title: "pages/WorkspacePage/AgentAlert",
+	component: AgentAlert,
 	args: {
 		title: "Something went wrong",
 		detail:
@@ -13,7 +13,7 @@ const meta: Meta<typeof WorkspaceAlert> = {
 };
 
 export default meta;
-type Story = StoryObj<typeof WorkspaceAlert>;
+type Story = StoryObj<typeof AgentAlert>;
 
 export const WarningProminent: Story = {
 	args: {
diff --git a/site/src/pages/WorkspacePage/WorkspaceAlert.tsx b/site/src/pages/WorkspacePage/AgentAlert.tsx
similarity index 56%
rename from site/src/pages/WorkspacePage/WorkspaceAlert.tsx
rename to site/src/pages/WorkspacePage/AgentAlert.tsx
index 0343309856..3d40843c02 100644
--- a/site/src/pages/WorkspacePage/WorkspaceAlert.tsx
+++ b/site/src/pages/WorkspacePage/AgentAlert.tsx
@@ -1,16 +1,16 @@
 import type { FC } from "react";
 import { Alert, AlertDescription, AlertTitle } from "#/components/Alert/Alert";
-import { Link } from "#/components/Link/Link";
+import { Button } from "#/components/Button/Button";
 
-interface WorkspaceAlertProps {
+interface AgentAlertProps {
 	title: string;
 	detail: string;
 	severity: "info" | "warning";
 	prominent: boolean;
-	troubleshootingURL: string | undefined;
+	troubleshootingURL?: string;
 }
 
-export const WorkspaceAlert: FC<WorkspaceAlertProps> = ({
+export const AgentAlert: FC<AgentAlertProps> = ({
 	title,
 	detail,
 	severity,
@@ -21,14 +21,14 @@ export const WorkspaceAlert: FC<WorkspaceAlertProps> = ({
 		<Alert severity={severity} prominent={prominent}>
 			<AlertTitle>{title}</AlertTitle>
 			<AlertDescription>
-				<p>{detail}</p>
-				<p>
-					{troubleshootingURL && (
-						<Link href={troubleshootingURL} target="_blank">
+				<div className="mb-2">{detail}</div>
+				{troubleshootingURL && (
+					<Button size="sm" asChild>
+						<a href={troubleshootingURL} target="_blank" rel="noopener">
 							View docs to troubleshoot
-						</Link>
-					)}
-				</p>
+						</a>
+					</Button>
+				)}
 			</AlertDescription>
 		</Alert>
 	);
diff --git a/site/src/pages/WorkspacePage/Workspace.tsx b/site/src/pages/WorkspacePage/Workspace.tsx
index 8a3e6c8d55..f1ca8fdb66 100644
--- a/site/src/pages/WorkspacePage/Workspace.tsx
+++ b/site/src/pages/WorkspacePage/Workspace.tsx
@@ -7,21 +7,18 @@ import { SidebarIconButton } from "#/components/FullPageLayout/Sidebar";
 import { useSearchParamsKey } from "#/hooks/useSearchParamsKey";
 import { ProvisionerStatusAlert } from "#/modules/provisioners/ProvisionerStatusAlert";
 import { AgentRow } from "#/modules/resources/AgentRow";
-import { getAgentHealthIssue } from "#/modules/workspaces/health";
 import { WorkspaceTimings } from "#/modules/workspaces/WorkspaceTiming/WorkspaceTimings";
 import type { WorkspacePermissions } from "../../modules/workspaces/permissions";
 import { HistorySidebar } from "./HistorySidebar";
 import { ResourceMetadata } from "./ResourceMetadata";
 import { ResourcesSidebar } from "./ResourcesSidebar";
 import { resourceOptionValue, useResourcesNav } from "./useResourcesNav";
-import { WorkspaceAlert } from "./WorkspaceAlert";
 import { WorkspaceBuildLogsSection } from "./WorkspaceBuildLogsSection";
 import {
 	getActiveTransitionStats,
 	WorkspaceBuildProgress,
 } from "./WorkspaceBuildProgress";
 import { WorkspaceDeletedBanner } from "./WorkspaceDeletedBanner";
-import { findTroubleshootingURL } from "./WorkspaceNotifications/WorkspaceNotifications";
 import { WorkspaceTopbar } from "./WorkspaceTopbar";
 
 interface WorkspaceProps {
@@ -99,7 +96,6 @@ export const Workspace: FC<WorkspaceProps> = ({
 		(workspace.latest_build.matched_provisioners?.available ?? 1) > 0;
 	const shouldShowProvisionerAlert =
 		workspacePending && !haveBuildLogs && !provisionersHealthy && !isRestarting;
-	const troubleshootingURL = findTroubleshootingURL(workspace.latest_build);
 
 	return (
 		<div className="flex flex-col flex-1 min-h-0">
@@ -195,13 +191,6 @@ export const Workspace: FC<WorkspaceProps> = ({
 								</Alert>
 							)}
 
-							{!workspace.health.healthy && (
-								<WorkspaceAlert
-									{...getAgentHealthIssue(workspace)}
-									troubleshootingURL={troubleshootingURL}
-								/>
-							)}
-
 							{transitionStats !== undefined && (
 								<WorkspaceBuildProgress
 									workspace={workspace}
diff --git a/site/src/pages/WorkspacePage/WorkspaceNotifications/WorkspaceNotifications.stories.tsx b/site/src/pages/WorkspacePage/WorkspaceNotifications/WorkspaceNotifications.stories.tsx
index 7a94a8001f..9fcc81fb16 100644
--- a/site/src/pages/WorkspacePage/WorkspaceNotifications/WorkspaceNotifications.stories.tsx
+++ b/site/src/pages/WorkspacePage/WorkspaceNotifications/WorkspaceNotifications.stories.tsx
@@ -156,7 +156,7 @@ export const StartupScriptFailed: Story = {
 			await userEvent.hover(screen.getByTestId("warning-notifications"));
 			await waitFor(() =>
 				expect(screen.getByRole("tooltip")).toHaveTextContent(
-					/startup script failed/i,
+					/one or more workspace agents need attention/i,
 				),
 			);
 		});
@@ -177,7 +177,7 @@ export const AgentDisconnected: Story = {
 			await userEvent.hover(screen.getByTestId("warning-notifications"));
 			await waitFor(() =>
 				expect(screen.getByRole("tooltip")).toHaveTextContent(
-					/agent has disconnected/i,
+					/one or more workspace agents need attention/i,
 				),
 			);
 		});
@@ -198,7 +198,7 @@ export const AgentTimeout: Story = {
 			await userEvent.hover(screen.getByTestId("warning-notifications"));
 			await waitFor(() =>
 				expect(screen.getByRole("tooltip")).toHaveTextContent(
-					/taking longer than expected/i,
+					/one or more workspace agents need attention/i,
 				),
 			);
 		});
diff --git a/site/src/pages/WorkspacePage/WorkspaceNotifications/WorkspaceNotifications.tsx b/site/src/pages/WorkspacePage/WorkspaceNotifications/WorkspaceNotifications.tsx
index bc34eb6c97..019a656667 100644
--- a/site/src/pages/WorkspacePage/WorkspaceNotifications/WorkspaceNotifications.tsx
+++ b/site/src/pages/WorkspacePage/WorkspaceNotifications/WorkspaceNotifications.tsx
@@ -13,7 +13,6 @@ import type {
 import { MemoizedInlineMarkdown } from "#/components/Markdown/InlineMarkdown";
 import { useDashboard } from "#/modules/dashboard/useDashboard";
 import { TemplateUpdateMessage } from "#/modules/templates/TemplateUpdateMessage";
-import { getAgentHealthIssue } from "#/modules/workspaces/health";
 
 dayjs.extend(relativeTime);
 
@@ -93,12 +92,10 @@ export const WorkspaceNotifications: FC<WorkspaceNotificationsProps> = ({
 	) {
 		const troubleshootingURL = findTroubleshootingURL(workspace.latest_build);
 		const hasActions = permissions.updateWorkspace || troubleshootingURL;
-		const healthIssue = getAgentHealthIssue(workspace);
-
 		notifications.push({
-			title: healthIssue.title,
-			severity: healthIssue.severity,
-			detail: healthIssue.detail,
+			title: "One or more workspace agents need attention",
+			severity: "warning",
+			detail: "Expand an agent's logs to view per-agent health details.",
 			actions: hasActions ? (
 				<>
 					{permissions.updateWorkspace && (
@@ -270,7 +267,7 @@ const styles = {
 	},
 } satisfies Record<string, Interpolation<Theme>>;
 
-export const findTroubleshootingURL = (
+const findTroubleshootingURL = (
 	workspaceBuild: WorkspaceBuild,
 ): string | undefined => {
 	for (const resource of workspaceBuild.resources) {