diff --git a/frontend/src/main.ts b/frontend/src/main.ts
index c408e41c9..835440a01 100644
--- a/frontend/src/main.ts
+++ b/frontend/src/main.ts
@@ -478,6 +478,7 @@ async function refreshDaemonStatus(): Promise<DaemonStatus> {
 		setDaemonStatus({
 			state: "stopped",
 			message: "AO daemon is no longer reachable.",
+			code: "daemon_unreachable",
 		});
 	}
 	return daemonStatus;
@@ -518,6 +519,7 @@ async function startDaemonInner(startEpoch: number): Promise<DaemonStatus> {
 		setDaemonStatus({
 			state: "stopped",
 			message: "AO_DAEMON_COMMAND is not configured; renderer uses loopback REST when available.",
+			code: "not_configured",
 		});
 		return daemonStatus;
 	}
@@ -640,6 +642,7 @@ async function startDaemonInner(startEpoch: number): Promise<DaemonStatus> {
 		setDaemonStatus({
 			state: "error",
 			message: `Bundled AO daemon binary was not found at ${launch.command}. Rebuild the desktop package.`,
+			code: "binary_missing",
 		});
 		return daemonStatus;
 	}
@@ -737,6 +740,7 @@ async function startDaemonInner(startEpoch: number): Promise<DaemonStatus> {
 			state: "ready",
 			port: process.env.AO_PORT ? Number(process.env.AO_PORT) : undefined,
 			message: "Daemon port not confirmed from logs or running.json; assuming the configured port.",
+			code: "port_unconfirmed",
 		});
 	}, PORT_DISCOVERY_TIMEOUT_MS);
 
@@ -745,17 +749,29 @@ async function startDaemonInner(startEpoch: number): Promise<DaemonStatus> {
 		if (daemonProcess !== child) return;
 		daemonProcess = null;
 		if (daemonStoppingProcess === child) daemonStoppingProcess = null;
-		setDaemonStatus({ state: "error", message: error.message });
+		setDaemonStatus({ state: "error", message: error.message, code: "spawn_failed" });
 	});
 
 	child.once("exit", (code, signal) => {
 		stopDiscovery();
 		if (daemonProcess !== child) return;
 		daemonProcess = null;
-		if (daemonStoppingProcess === child) daemonStoppingProcess = null;
+		// An explicit stopDaemon() already set a clean `{ state: "stopped" }`.
+		// daemon-telemetry reports any status carrying a `code` as
+		// ao.renderer.daemon_failure, so don't stamp `code: "exited"` on a stop
+		// the user or app asked for — that would count intentional stops as
+		// failures. Preserve the clean stopped status instead.
+		if (daemonStoppingProcess === child) {
+			daemonStoppingProcess = null;
+			setDaemonStatus({ state: "stopped" });
+			return;
+		}
 		setDaemonStatus({
 			state: "stopped",
 			message: signal ? `Daemon exited with ${signal}` : `Daemon exited with code ${code ?? "unknown"}`,
+			code: "exited",
+			exitCode: code,
+			signal,
 		});
 	});
 
diff --git a/frontend/src/renderer/components/NewTaskDialog.tsx b/frontend/src/renderer/components/NewTaskDialog.tsx
index 80a9bcddc..a51f379d9 100644
--- a/frontend/src/renderer/components/NewTaskDialog.tsx
+++ b/frontend/src/renderer/components/NewTaskDialog.tsx
@@ -7,6 +7,7 @@ import { Input } from "./ui/input";
 import { RequiredAgentField } from "./CreateProjectAgentSheet";
 import type { components } from "../../api/schema";
 import { apiClient, apiErrorMessage } from "../lib/api-client";
+import { captureRendererEvent } from "../lib/telemetry";
 import type { AgentProvider } from "../types/workspace";
 import { agentsQueryKey, agentsQueryOptions, refreshAgents } from "../hooks/useAgentsQuery";
 
@@ -88,6 +89,7 @@ export function NewTaskDialog({ open, projectId, onCreated, onOpenChange }: NewT
 
 		setIsSubmitting(true);
 		setError(undefined);
+		void captureRendererEvent("ao.renderer.task_create_requested", { project_id: projectId });
 		try {
 			const { data, error: apiError } = await apiClient.POST("/api/v1/sessions", {
 				body: {
@@ -101,9 +103,11 @@ export function NewTaskDialog({ open, projectId, onCreated, onOpenChange }: NewT
 			});
 			if (apiError) throw new Error(apiErrorMessage(apiError, "Unable to start task"));
 			if (!data?.session?.id) throw new Error("Task creation returned no session");
+			void captureRendererEvent("ao.renderer.task_create_succeeded", { project_id: projectId });
 			onCreated(data.session.id);
 			onOpenChange(false);
 		} catch (err) {
+			void captureRendererEvent("ao.renderer.task_create_failed", { project_id: projectId });
 			void queryClient.invalidateQueries({ queryKey: agentsQueryKey });
 			setError(err instanceof Error ? err.message : "Unable to start task");
 		} finally {
diff --git a/frontend/src/renderer/components/NotificationCenter.tsx b/frontend/src/renderer/components/NotificationCenter.tsx
index 582205261..02da22b80 100644
--- a/frontend/src/renderer/components/NotificationCenter.tsx
+++ b/frontend/src/renderer/components/NotificationCenter.tsx
@@ -10,6 +10,7 @@ import {
 import { aoBridge } from "../lib/bridge";
 import { formatTimeCompact } from "../lib/format-time";
 import { createNotificationsTransport, type NotificationDTO, unreadNotificationsQueryKey } from "../lib/notifications";
+import { captureRendererEvent } from "../lib/telemetry";
 import { cn } from "../lib/utils";
 import {
 	DropdownMenu,
@@ -37,11 +38,13 @@ export function NotificationCenter({ style }: NotificationCenterProps) {
 		(notification: NotificationDTO) => {
 			const target = notification.target;
 			if (target.kind === "pr" && target.prUrl) {
+				void captureRendererEvent("ao.renderer.notification_opened", { target: "pr" });
 				window.open(target.prUrl, "_blank", "noopener,noreferrer");
 				return;
 			}
 			const sessionId = target.sessionId || notification.sessionId;
 			if (!sessionId) return;
+			void captureRendererEvent("ao.renderer.notification_opened", { target: "session" });
 			if (notification.projectId) {
 				void navigate({
 					to: "/projects/$projectId/sessions/$sessionId",
@@ -66,6 +69,7 @@ export function NotificationCenter({ style }: NotificationCenterProps) {
 
 	const markOneRead = async (id: string) => {
 		setActionError(null);
+		void captureRendererEvent("ao.renderer.notification_marked_read", { scope: "single" });
 		try {
 			await markRead.mutateAsync(id);
 		} catch (error) {
@@ -75,6 +79,7 @@ export function NotificationCenter({ style }: NotificationCenterProps) {
 
 	const markAll = async () => {
 		setActionError(null);
+		void captureRendererEvent("ao.renderer.notification_marked_read", { scope: "all" });
 		try {
 			await markAllRead.mutateAsync();
 		} catch (error) {
diff --git a/frontend/src/renderer/components/ProjectSettingsForm.tsx b/frontend/src/renderer/components/ProjectSettingsForm.tsx
index 513567027..f9a815678 100644
--- a/frontend/src/renderer/components/ProjectSettingsForm.tsx
+++ b/frontend/src/renderer/components/ProjectSettingsForm.tsx
@@ -4,6 +4,7 @@ import type { components } from "../../api/schema";
 import { agentsQueryKey, agentsQueryOptions, refreshAgents } from "../hooks/useAgentsQuery";
 import { useWorkspaceQuery, workspaceQueryKey } from "../hooks/useWorkspaceQuery";
 import { apiClient, apiErrorMessage } from "../lib/api-client";
+import { captureRendererEvent } from "../lib/telemetry";
 import { spawnOrchestrator } from "../lib/spawn-orchestrator";
 import { newestActiveOrchestrator } from "../types/workspace";
 import { RequiredAgentField } from "./CreateProjectAgentSheet";
@@ -120,6 +121,7 @@ function SettingsBody({ project, projectId, onSaved }: { project: Project; proje
 
 	const mutation = useMutation({
 		mutationFn: async () => {
+			void captureRendererEvent("ao.renderer.settings_save_requested", { project_id: projectId });
 			// PUT replaces the whole config; merge the edited fields over what loaded
 			// so we don't drop env/symlinks/postCreate the form doesn't expose.
 			const next: ProjectConfig = {
@@ -146,7 +148,7 @@ function SettingsBody({ project, projectId, onSaved }: { project: Project; proje
 				(activeOrchestrator && activeOrchestrator.provider !== form.orchestratorAgent)
 			) {
 				try {
-					await spawnOrchestrator(projectId, true);
+					await spawnOrchestrator(projectId, "settings", true);
 				} catch (error) {
 					return {
 						replacementError: error instanceof Error ? error.message : "Could not replace orchestrator",
@@ -156,12 +158,16 @@ function SettingsBody({ project, projectId, onSaved }: { project: Project; proje
 			return { replacementError: null };
 		},
 		onSuccess: (result) => {
+			void captureRendererEvent("ao.renderer.settings_save_succeeded", { project_id: projectId });
 			setSavedAt(Date.now());
 			setReplacementError(result.replacementError);
 			setValidationError(null);
 			void queryClient.invalidateQueries({ queryKey: ["project", projectId] });
 			onSaved();
 		},
+		onError: () => {
+			void captureRendererEvent("ao.renderer.settings_save_failed", { project_id: projectId });
+		},
 	});
 
 	return (
diff --git a/frontend/src/renderer/components/RestoreUnavailableDialog.tsx b/frontend/src/renderer/components/RestoreUnavailableDialog.tsx
index d5f99d338..f568cc01d 100644
--- a/frontend/src/renderer/components/RestoreUnavailableDialog.tsx
+++ b/frontend/src/renderer/components/RestoreUnavailableDialog.tsx
@@ -22,7 +22,7 @@ export function RestoreUnavailableDialog({ open, session, onOpenChange, onRecrea
 		setBusy(true);
 		setError(undefined);
 		try {
-			const id = await spawnOrchestrator(session.workspaceId, true);
+			const id = await spawnOrchestrator(session.workspaceId, "restore_dialog", true);
 			onOpenChange(false);
 			onRecreated(id);
 		} catch (err) {
diff --git a/frontend/src/renderer/components/SessionsBoard.tsx b/frontend/src/renderer/components/SessionsBoard.tsx
index ae7f12e7f..0103a5c30 100644
--- a/frontend/src/renderer/components/SessionsBoard.tsx
+++ b/frontend/src/renderer/components/SessionsBoard.tsx
@@ -117,7 +117,7 @@ export function SessionsBoard({ projectId }: SessionsBoardProps) {
 		}
 		setIsSpawning(true);
 		try {
-			const sessionId = await spawnOrchestrator(projectId);
+			const sessionId = await spawnOrchestrator(projectId, "board");
 			await queryClient.invalidateQueries({ queryKey: workspaceQueryKey });
 			void navigate({
 				to: "/projects/$projectId/sessions/$sessionId",
diff --git a/frontend/src/renderer/components/ShellTopbar.tsx b/frontend/src/renderer/components/ShellTopbar.tsx
index 2929475c7..892fcabbd 100644
--- a/frontend/src/renderer/components/ShellTopbar.tsx
+++ b/frontend/src/renderer/components/ShellTopbar.tsx
@@ -112,7 +112,7 @@ export function ShellTopbar() {
 		}
 		setIsSpawning(true);
 		try {
-			const sessionId = await spawnOrchestrator(projectId);
+			const sessionId = await spawnOrchestrator(projectId, "topbar");
 			await queryClient.invalidateQueries({ queryKey: workspaceQueryKey });
 			void navigate({
 				to: "/projects/$projectId/sessions/$sessionId",
@@ -252,16 +252,21 @@ export function TopbarKillButton({ session }: { session: WorkspaceSession }) {
 
 	const kill = useMutation({
 		mutationFn: async () => {
+			void captureRendererEvent("ao.renderer.session_kill_requested", { project_id: session.workspaceId });
 			const { error: apiError } = await apiClient.POST("/api/v1/sessions/{sessionId}/kill", {
 				params: { path: { sessionId: session.id } },
 			});
 			if (apiError) throw new Error(apiErrorMessage(apiError));
 		},
 		onSuccess: () => {
+			void captureRendererEvent("ao.renderer.session_kill_succeeded", { project_id: session.workspaceId });
 			setConfirming(false);
 			void queryClient.invalidateQueries({ queryKey: workspaceQueryKey });
 		},
-		onError: (e) => setError(e instanceof Error ? e.message : "Kill failed"),
+		onError: (e) => {
+			void captureRendererEvent("ao.renderer.session_kill_failed", { project_id: session.workspaceId });
+			setError(e instanceof Error ? e.message : "Kill failed");
+		},
 	});
 
 	if (confirming) {
diff --git a/frontend/src/renderer/components/Sidebar.tsx b/frontend/src/renderer/components/Sidebar.tsx
index eb54439e8..89c480fe9 100644
--- a/frontend/src/renderer/components/Sidebar.tsx
+++ b/frontend/src/renderer/components/Sidebar.tsx
@@ -445,7 +445,7 @@ function ProjectItem({
 		}
 		setIsSpawning(true);
 		try {
-			const sessionId = await spawnOrchestrator(workspace.id);
+			const sessionId = await spawnOrchestrator(workspace.id, "sidebar");
 			await queryClient.invalidateQueries({ queryKey: workspaceQueryKey });
 			selection.goSession(workspace.id, sessionId);
 		} catch (err) {
diff --git a/frontend/src/renderer/hooks/useTerminalSession.ts b/frontend/src/renderer/hooks/useTerminalSession.ts
index 70365e350..0ecfcfc21 100644
--- a/frontend/src/renderer/hooks/useTerminalSession.ts
+++ b/frontend/src/renderer/hooks/useTerminalSession.ts
@@ -10,6 +10,7 @@
 import { useQueryClient } from "@tanstack/react-query";
 import { useCallback, useEffect, useRef, useState } from "react";
 import { getApiBaseUrl } from "../lib/api-client";
+import { captureRendererEvent } from "../lib/telemetry";
 import { createTerminalMux, muxUrlFromApiBase, type TerminalMux } from "../lib/terminal-mux";
 import type { WorkspaceSession } from "../types/workspace";
 import { workspaceQueryKey } from "./useWorkspaceQuery";
@@ -213,6 +214,7 @@ export function useTerminalSession(session: WorkspaceSession | undefined, option
 				terminal.writeln(`\r\n\x1b[2m[terminal error] ${message}\x1b[0m`);
 				setError(message);
 				transition("error");
+				void captureRendererEvent("ao.renderer.terminal_attach_failed", { reason: "pane_error" });
 				invalidateWorkspaces();
 			}),
 			mux.onConnectionChange((connectionState) => {
@@ -268,6 +270,11 @@ export function useTerminalSession(session: WorkspaceSession | undefined, option
 		r.openTimer = setTimeout(() => {
 			if (!isCurrentAttachment(generation, handle, mux)) return;
 			r.openTimer = null;
+			// Only the first timeout of a reattach sequence is reported; the
+			// backoff loop retrying against a restarting daemon is not news.
+			if (r.attempts === 0) {
+				void captureRendererEvent("ao.renderer.terminal_attach_failed", { reason: "open_timeout" });
+			}
 			transition("reattaching");
 			teardownMux();
 			scheduleReattach();
diff --git a/frontend/src/renderer/lib/api-client.test.ts b/frontend/src/renderer/lib/api-client.test.ts
index df7898253..fe527981f 100644
--- a/frontend/src/renderer/lib/api-client.test.ts
+++ b/frontend/src/renderer/lib/api-client.test.ts
@@ -1,12 +1,20 @@
-import { afterEach, describe, expect, it, vi } from "vitest";
+import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
 import {
 	apiClient,
 	apiErrorMessage,
 	getApiBaseUrl,
 	hasTrustedApiBaseUrl,
+	normalizeApiOperation,
 	setApiBaseUrl,
 	subscribeApiBaseUrl,
 } from "./api-client";
+import { captureRendererEvent } from "./telemetry";
+
+vi.mock("./telemetry", () => ({
+	captureRendererEvent: vi.fn().mockResolvedValue(undefined),
+}));
+
+const captureMock = vi.mocked(captureRendererEvent);
 
 describe("apiClient runtime base URL", () => {
 	afterEach(() => {
@@ -162,6 +170,123 @@ describe("subscribeApiBaseUrl", () => {
 	});
 });
 
+describe("normalizeApiOperation", () => {
+	it("replaces identifier segments after resource collections", () => {
+		expect(normalizeApiOperation("get", "/api/v1/projects/my project id")).toBe("GET /api/v1/projects/:id");
+		expect(normalizeApiOperation("POST", "/api/v1/sessions/ao-42/kill")).toBe("POST /api/v1/sessions/:id/kill");
+		expect(normalizeApiOperation("PUT", "/api/v1/projects/p1/config")).toBe("PUT /api/v1/projects/:id/config");
+	});
+
+	it("leaves collection and non-resource paths untouched", () => {
+		expect(normalizeApiOperation("GET", "/api/v1/projects")).toBe("GET /api/v1/projects");
+		expect(normalizeApiOperation("POST", "/api/v1/orchestrators")).toBe("POST /api/v1/orchestrators");
+	});
+
+	it("keeps static child routes instead of treating them as ids", () => {
+		// These match an exact OpenAPI template, so the trailing segment must not
+		// be collapsed to :id (which would break aggregation and hide the route).
+		expect(normalizeApiOperation("POST", "/api/v1/notifications/read-all")).toBe("POST /api/v1/notifications/read-all");
+		expect(normalizeApiOperation("POST", "/api/v1/sessions/cleanup")).toBe("POST /api/v1/sessions/cleanup");
+	});
+
+	it("normalizes ids for resources a collection heuristic would miss", () => {
+		expect(normalizeApiOperation("GET", "/api/v1/orchestrators/orch-abc")).toBe("GET /api/v1/orchestrators/:id");
+		expect(normalizeApiOperation("POST", "/api/v1/prs/pr-1/merge")).toBe("POST /api/v1/prs/:id/merge");
+	});
+});
+
+describe("api error telemetry", () => {
+	// The dedupe window keys off Date.now(); jump the clock far past any
+	// earlier test's reports so each test starts with a clean window.
+	let clock = Date.UTC(2100, 0, 1);
+	beforeEach(() => {
+		vi.useFakeTimers({ toFake: ["Date"] });
+		clock += 10 * 60_000;
+		vi.setSystemTime(clock);
+		captureMock.mockClear();
+	});
+	afterEach(() => {
+		vi.useRealTimers();
+		vi.restoreAllMocks();
+		setApiBaseUrl("http://127.0.0.1:3001");
+	});
+
+	it("reports http_5xx with a normalized operation", async () => {
+		vi.spyOn(globalThis, "fetch").mockResolvedValue(new Response("oops", { status: 500 }));
+		setApiBaseUrl("http://127.0.0.1:3037");
+
+		await apiClient.GET("/api/v1/projects");
+
+		expect(captureMock).toHaveBeenCalledWith("ao.renderer.api_error", {
+			operation: "GET /api/v1/projects",
+			error_category: "http_5xx",
+			status: 500,
+		});
+	});
+
+	it("reports http_4xx with ids stripped from the operation", async () => {
+		vi.spyOn(globalThis, "fetch").mockResolvedValue(new Response("nope", { status: 404 }));
+		setApiBaseUrl("http://127.0.0.1:3037");
+
+		await apiClient.POST("/api/v1/sessions/{sessionId}/kill", {
+			params: { path: { sessionId: "ao-raw-id" } },
+		});
+
+		expect(captureMock).toHaveBeenCalledWith("ao.renderer.api_error", {
+			operation: "POST /api/v1/sessions/:id/kill",
+			error_category: "http_4xx",
+			status: 404,
+		});
+	});
+
+	it("reports network_error and rethrows", async () => {
+		vi.spyOn(globalThis, "fetch").mockRejectedValue(new TypeError("Failed to fetch"));
+		setApiBaseUrl("http://127.0.0.1:3037");
+
+		await expect(apiClient.GET("/api/v1/projects")).rejects.toThrow("Failed to fetch");
+
+		expect(captureMock).toHaveBeenCalledWith("ao.renderer.api_error", {
+			operation: "GET /api/v1/projects",
+			error_category: "network_error",
+			status: undefined,
+		});
+	});
+
+	it("does not report caller-initiated aborts", async () => {
+		vi.spyOn(globalThis, "fetch").mockRejectedValue(new DOMException("Aborted", "AbortError"));
+		setApiBaseUrl("http://127.0.0.1:3037");
+
+		await expect(apiClient.GET("/api/v1/projects")).rejects.toThrow("Aborted");
+
+		expect(captureMock).not.toHaveBeenCalled();
+	});
+
+	it("reports daemon_unavailable when the base URL is untrusted", async () => {
+		setApiBaseUrl(null);
+
+		await apiClient.GET("/api/v1/projects");
+
+		expect(captureMock).toHaveBeenCalledWith("ao.renderer.api_error", {
+			operation: "GET /api/v1/projects",
+			error_category: "daemon_unavailable",
+			status: 503,
+		});
+	});
+
+	it("dedupes repeated identical failures within the 30s window", async () => {
+		vi.spyOn(globalThis, "fetch").mockImplementation(async () => new Response("oops", { status: 502 }));
+		setApiBaseUrl("http://127.0.0.1:3037");
+
+		await apiClient.GET("/api/v1/projects");
+		await apiClient.GET("/api/v1/projects");
+		expect(captureMock).toHaveBeenCalledTimes(1);
+
+		vi.setSystemTime(clock + 31_000);
+		await apiClient.GET("/api/v1/projects");
+		expect(captureMock).toHaveBeenCalledTimes(2);
+	});
+});
+
 describe("apiErrorMessage", () => {
 	it("preserves daemon error codes next to human messages", () => {
 		expect(apiErrorMessage({ code: "AGENT_BINARY_NOT_FOUND", message: "agent binary not found on PATH" })).toBe(
diff --git a/frontend/src/renderer/lib/api-client.ts b/frontend/src/renderer/lib/api-client.ts
index 8bc2551aa..6afdecde1 100644
--- a/frontend/src/renderer/lib/api-client.ts
+++ b/frontend/src/renderer/lib/api-client.ts
@@ -1,5 +1,6 @@
 import createClient from "openapi-fetch";
 import type { paths } from "../../api/schema";
+import { captureRendererEvent } from "./telemetry";
 
 function devApiBaseUrl(): string {
 	return typeof window === "undefined" ? "http://127.0.0.1:3001" : window.location.origin;
@@ -39,43 +40,179 @@ export function setApiBaseUrl(nextBaseUrl: string | null): void {
 	baseUrlListeners.forEach((listener) => listener());
 }
 
+// Route templates from the generated OpenAPI schema (frontend/src/api/schema.ts).
+// Operation strings sent to telemetry must never contain raw IDs (project IDs
+// are user-chosen strings), so we match each request path against these
+// templates and report the template — collapsing `{param}` to `:id` — rather
+// than guessing which segments are identifiers. Matching from the schema keeps
+// static child routes (notifications/read-all, sessions/cleanup) intact and
+// still normalizes IDs for every resource, including ones a segment heuristic
+// would miss (orchestrators/{id}). Keep in sync with schema.ts.
+const ROUTE_TEMPLATES = [
+	"/api/v1/events",
+	"/api/v1/import",
+	"/api/v1/notifications",
+	"/api/v1/notifications/{id}",
+	"/api/v1/notifications/read-all",
+	"/api/v1/notifications/stream",
+	"/api/v1/orchestrators",
+	"/api/v1/orchestrators/{id}",
+	"/api/v1/projects",
+	"/api/v1/projects/{id}",
+	"/api/v1/projects/{id}/config",
+	"/api/v1/prs/{id}/merge",
+	"/api/v1/prs/{id}/resolve-comments",
+	"/api/v1/sessions",
+	"/api/v1/sessions/{sessionId}",
+	"/api/v1/sessions/{sessionId}/activity",
+	"/api/v1/sessions/{sessionId}/kill",
+	"/api/v1/sessions/{sessionId}/pr",
+	"/api/v1/sessions/{sessionId}/pr/claim",
+	"/api/v1/sessions/{sessionId}/preview",
+	"/api/v1/sessions/{sessionId}/preview/files/*",
+	"/api/v1/sessions/{sessionId}/restore",
+	"/api/v1/sessions/{sessionId}/reviews",
+	"/api/v1/sessions/{sessionId}/reviews/submit",
+	"/api/v1/sessions/{sessionId}/reviews/trigger",
+	"/api/v1/sessions/{sessionId}/rollback",
+	"/api/v1/sessions/{sessionId}/send",
+	"/api/v1/sessions/cleanup",
+] as const;
+
+// Resource collections whose next path segment is an identifier. Only used as a
+// defensive fallback for paths not covered by ROUTE_TEMPLATES; keeps IDs out of
+// telemetry for known collections even if a route is ever missed above.
+const RESOURCE_SEGMENTS = new Set(["projects", "sessions", "notifications", "workspaces", "prs", "orchestrators"]);
+
+// Match a path against one template. `{param}` matches any single segment
+// (reported as `:id`), a trailing `*` matches the remaining path, and every
+// other segment must match literally. Returns the normalized template plus a
+// score = number of literal segments matched, so the most specific template
+// wins when several match (e.g. `read-all` beats `{id}`).
+function matchRouteTemplate(pathname: string, template: string): { normalized: string; score: number } | null {
+	const pathSegs = pathname.split("/");
+	const tmplSegs = template.split("/");
+	const out: string[] = [];
+	let score = 0;
+	for (let i = 0; i < tmplSegs.length; i += 1) {
+		const t = tmplSegs[i];
+		if (t === "*") {
+			out.push("*");
+			return { normalized: out.join("/"), score };
+		}
+		const p = pathSegs[i];
+		if (p === undefined) return null;
+		if (t.startsWith("{") && t.endsWith("}")) {
+			out.push(":id");
+		} else if (t === p) {
+			out.push(t);
+			score += 1;
+		} else {
+			return null;
+		}
+	}
+	if (pathSegs.length !== tmplSegs.length) return null;
+	return { normalized: out.join("/"), score };
+}
+
+function fallbackNormalize(pathname: string): string {
+	const segments = pathname.split("/");
+	for (let i = 0; i < segments.length - 1; i += 1) {
+		if (RESOURCE_SEGMENTS.has(segments[i]) && segments[i + 1]) {
+			segments[i + 1] = ":id";
+			i += 1;
+		}
+	}
+	return segments.join("/");
+}
+
+export function normalizeApiOperation(method: string, pathname: string): string {
+	let best: { normalized: string; score: number } | null = null;
+	for (const template of ROUTE_TEMPLATES) {
+		const match = matchRouteTemplate(pathname, template);
+		if (match && (best === null || match.score > best.score)) best = match;
+	}
+	return `${method.toUpperCase()} ${best?.normalized ?? fallbackNormalize(pathname)}`;
+}
+
+type ApiErrorCategory = "daemon_unavailable" | "network_error" | "http_4xx" | "http_5xx";
+
+// One event per (operation, category, status) per window: a daemon outage
+// makes every polling query fail at once and on every retry — the failure
+// signal matters, the storm does not.
+const API_ERROR_DEDUPE_MS = 30_000;
+const lastApiErrorAt = new Map<string, number>();
+
+function reportApiError(operation: string, category: ApiErrorCategory, status?: number): void {
+	const key = `${operation}|${category}|${status ?? ""}`;
+	const now = Date.now();
+	const last = lastApiErrorAt.get(key);
+	if (last !== undefined && now - last < API_ERROR_DEDUPE_MS) return;
+	lastApiErrorAt.set(key, now);
+	void captureRendererEvent("ao.renderer.api_error", {
+		operation,
+		error_category: category,
+		status,
+	});
+}
+
 async function runtimeFetch(input: Request): Promise<Response> {
+	const operation = normalizeApiOperation(input.method, new URL(input.url).pathname);
 	const baseUrl = runtimeApiBaseUrl;
 	if (baseUrl === null) {
+		reportApiError(operation, "daemon_unavailable", 503);
 		return new Response(JSON.stringify({ message: "AO daemon is not ready." }), {
 			status: 503,
 			headers: { "Content-Type": "application/json" },
 		});
 	}
-	if (!baseUrl) {
-		return fetch(input);
-	}
 
-	const url = new URL(input.url);
-	const target = new URL(url.pathname + url.search + url.hash, baseUrl);
-	if (target.href === input.url) {
-		return fetch(input);
-	}
+	const send = async (): Promise<Response> => {
+		if (!baseUrl) {
+			return fetch(input);
+		}
 
-	// Rebase onto the runtime base URL by copying fields explicitly and
-	// buffering the body. `new Request(target, input)` reads the source
-	// request's `duplex` getter, which Electron's Chromium lacks — it throws
-	// "The duplex member must be specified" for any request with a body, so
-	// every POST would fail in the packaged app. API bodies are small JSON;
-	// buffering sidesteps streaming-duplex semantics entirely.
-	const body = input.method === "GET" || input.method === "HEAD" ? undefined : await input.arrayBuffer();
-	return fetch(target, {
-		method: input.method,
-		headers: input.headers,
-		body,
-		signal: input.signal,
-		credentials: input.credentials,
-		cache: input.cache,
-		redirect: input.redirect,
-		referrerPolicy: input.referrerPolicy,
-		integrity: input.integrity,
-		keepalive: input.keepalive,
-	});
+		const url = new URL(input.url);
+		const target = new URL(url.pathname + url.search + url.hash, baseUrl);
+		if (target.href === input.url) {
+			return fetch(input);
+		}
+
+		// Rebase onto the runtime base URL by copying fields explicitly and
+		// buffering the body. `new Request(target, input)` reads the source
+		// request's `duplex` getter, which Electron's Chromium lacks — it throws
+		// "The duplex member must be specified" for any request with a body, so
+		// every POST would fail in the packaged app. API bodies are small JSON;
+		// buffering sidesteps streaming-duplex semantics entirely.
+		const body = input.method === "GET" || input.method === "HEAD" ? undefined : await input.arrayBuffer();
+		return fetch(target, {
+			method: input.method,
+			headers: input.headers,
+			body,
+			signal: input.signal,
+			credentials: input.credentials,
+			cache: input.cache,
+			redirect: input.redirect,
+			referrerPolicy: input.referrerPolicy,
+			integrity: input.integrity,
+			keepalive: input.keepalive,
+		});
+	};
+
+	let response: Response;
+	try {
+		response = await send();
+	} catch (error) {
+		// Caller-initiated aborts (unmounted components cancelling queries) are not failures.
+		if (!(error instanceof DOMException && error.name === "AbortError")) {
+			reportApiError(operation, "network_error");
+		}
+		throw error;
+	}
+	if (!response.ok) {
+		reportApiError(operation, response.status >= 500 ? "http_5xx" : "http_4xx", response.status);
+	}
+	return response;
 }
 
 export const apiClient = createClient<paths>({
diff --git a/frontend/src/renderer/lib/daemon-telemetry.test.ts b/frontend/src/renderer/lib/daemon-telemetry.test.ts
new file mode 100644
index 000000000..718f120cd
--- /dev/null
+++ b/frontend/src/renderer/lib/daemon-telemetry.test.ts
@@ -0,0 +1,119 @@
+import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
+import type { DaemonStatus } from "../../shared/daemon-status";
+import { aoBridge } from "./bridge";
+import { startDaemonFailureTelemetry } from "./daemon-telemetry";
+import { captureRendererEvent } from "./telemetry";
+
+vi.mock("./telemetry", () => ({
+	captureRendererEvent: vi.fn().mockResolvedValue(undefined),
+}));
+
+vi.mock("./bridge", () => ({
+	aoBridge: {
+		daemon: {
+			getStatus: vi.fn(),
+			onStatus: vi.fn(),
+		},
+	},
+}));
+
+const captureMock = vi.mocked(captureRendererEvent);
+const getStatusMock = vi.mocked(aoBridge.daemon.getStatus);
+const onStatusMock = vi.mocked(aoBridge.daemon.onStatus);
+
+describe("daemon failure telemetry", () => {
+	let pushStatus!: (status: DaemonStatus) => void;
+	let stop: () => void = () => undefined;
+
+	beforeEach(() => {
+		captureMock.mockClear();
+		onStatusMock.mockClear();
+		getStatusMock.mockResolvedValue({ state: "starting" });
+		onStatusMock.mockImplementation((listener) => {
+			pushStatus = listener;
+			return () => undefined;
+		});
+	});
+
+	afterEach(() => {
+		stop();
+	});
+
+	it("reports a failing status with coarse fields only", () => {
+		stop = startDaemonFailureTelemetry();
+
+		pushStatus({ state: "error", message: "spawn /Users/alice/ao failed", code: "spawn_failed" });
+
+		expect(captureMock).toHaveBeenCalledTimes(1);
+		expect(captureMock).toHaveBeenCalledWith("ao.renderer.daemon_failure", {
+			daemon_state: "error",
+			code: "spawn_failed",
+			exit_code: undefined,
+			signal: undefined,
+		});
+	});
+
+	it("includes exit code and signal for daemon exits", () => {
+		stop = startDaemonFailureTelemetry();
+
+		pushStatus({ state: "stopped", code: "exited", exitCode: 1, signal: "SIGKILL" });
+
+		expect(captureMock).toHaveBeenCalledWith("ao.renderer.daemon_failure", {
+			daemon_state: "stopped",
+			code: "exited",
+			exit_code: 1,
+			signal: "SIGKILL",
+		});
+	});
+
+	it("ignores statuses without a failure code (healthy or user-initiated stop)", () => {
+		stop = startDaemonFailureTelemetry();
+
+		pushStatus({ state: "ready", port: 3037 });
+		pushStatus({ state: "stopped" });
+
+		expect(captureMock).not.toHaveBeenCalled();
+	});
+
+	it("dedupes identical consecutive failures and resets on recovery", () => {
+		stop = startDaemonFailureTelemetry();
+
+		pushStatus({ state: "error", code: "daemon_unreachable" });
+		pushStatus({ state: "error", code: "daemon_unreachable" });
+		expect(captureMock).toHaveBeenCalledTimes(1);
+
+		// A different failure is a new event.
+		pushStatus({ state: "stopped", code: "exited", exitCode: 137 });
+		expect(captureMock).toHaveBeenCalledTimes(2);
+
+		// Recovery resets dedupe: the same failure recurring is reported again.
+		pushStatus({ state: "ready", port: 3037 });
+		pushStatus({ state: "error", code: "daemon_unreachable" });
+		expect(captureMock).toHaveBeenCalledTimes(3);
+	});
+
+	it("reports the initial status from getStatus on start", async () => {
+		getStatusMock.mockResolvedValue({ state: "error", code: "binary_missing" });
+
+		stop = startDaemonFailureTelemetry();
+		await vi.waitFor(() => expect(captureMock).toHaveBeenCalledTimes(1));
+
+		expect(captureMock).toHaveBeenCalledWith("ao.renderer.daemon_failure", {
+			daemon_state: "error",
+			code: "binary_missing",
+			exit_code: undefined,
+			signal: undefined,
+		});
+	});
+
+	it("is idempotent while started and restartable after stop", () => {
+		stop = startDaemonFailureTelemetry();
+		const noop = startDaemonFailureTelemetry();
+		expect(onStatusMock).toHaveBeenCalledTimes(1);
+		noop();
+
+		stop();
+		stop = startDaemonFailureTelemetry();
+		expect(onStatusMock).toHaveBeenCalledTimes(2);
+	});
+});
diff --git a/frontend/src/renderer/lib/daemon-telemetry.ts b/frontend/src/renderer/lib/daemon-telemetry.ts
new file mode 100644
index 000000000..a02987227
--- /dev/null
+++ b/frontend/src/renderer/lib/daemon-telemetry.ts
@@ -0,0 +1,53 @@
+// Daemon failures happen in the Electron main process, which has no PostHog
+// client. Main stamps a machine-readable `code` on every failing DaemonStatus
+// (shared/daemon-status.ts); this module rides the existing daemon:status IPC
+// push and reports those failures through the renderer's telemetry client.
+import type { DaemonStatus } from "../../shared/daemon-status";
+import { aoBridge } from "./bridge";
+import { captureRendererEvent } from "./telemetry";
+
+let started = false;
+let lastFailureKey: string | null = null;
+
+function failureKey(status: DaemonStatus): string | null {
+	if (!status.code) return null;
+	return [status.state, status.code, status.exitCode ?? "", status.signal ?? ""].join("|");
+}
+
+function reportStatus(status: DaemonStatus): void {
+	const key = failureKey(status);
+	if (!key) {
+		// Healthy status resets dedupe so a repeat failure after recovery is a new event.
+		lastFailureKey = null;
+		return;
+	}
+	if (key === lastFailureKey) return;
+	lastFailureKey = key;
+	void captureRendererEvent("ao.renderer.daemon_failure", {
+		daemon_state: status.state,
+		code: status.code,
+		exit_code: typeof status.exitCode === "number" ? status.exitCode : undefined,
+		signal: status.signal ?? undefined,
+	});
+}
+
+/** Idempotent; returns a stop function (used by tests). */
+export function startDaemonFailureTelemetry(): () => void {
+	if (started) return () => undefined;
+	started = true;
+	void aoBridge.daemon
+		.getStatus()
+		.then(reportStatus)
+		.catch(() => undefined);
+	let stopListener: () => void = () => undefined;
+	try {
+		stopListener = aoBridge.daemon.onStatus(reportStatus);
+	} catch {
+		// Preload bridge unavailable (browser preview): initial getStatus already handled.
+	}
+	return () => {
+		started = false;
+		lastFailureKey = null;
+		stopListener();
+	};
+}
diff --git a/frontend/src/renderer/lib/restart-orchestrator.test.ts b/frontend/src/renderer/lib/restart-orchestrator.test.ts
index 8b85b9bf8..a202fc21b 100644
--- a/frontend/src/renderer/lib/restart-orchestrator.test.ts
+++ b/frontend/src/renderer/lib/restart-orchestrator.test.ts
@@ -36,7 +36,7 @@ describe("restartProjectOrchestrator", () => {
 			onError,
 		});
 
-		expect(spawnMock).toHaveBeenCalledWith("proj-1", true);
+		expect(spawnMock).toHaveBeenCalledWith("proj-1", "restart", true);
 		expect(invalidateSpy).toHaveBeenCalledWith({ queryKey: workspaceQueryKey });
 		expect(setOrchestratorReplacementError).toHaveBeenNthCalledWith(1, "proj-1", null);
 		expect(setOrchestratorReplacementError).toHaveBeenNthCalledWith(2, "proj-1", "missing goose binary");
diff --git a/frontend/src/renderer/lib/restart-orchestrator.ts b/frontend/src/renderer/lib/restart-orchestrator.ts
index d921a4c80..c1619add1 100644
--- a/frontend/src/renderer/lib/restart-orchestrator.ts
+++ b/frontend/src/renderer/lib/restart-orchestrator.ts
@@ -36,7 +36,7 @@ export async function restartProjectOrchestrator({
 	setProjectRestarting(projectId, true);
 	setOrchestratorReplacementError(projectId, null);
 	try {
-		const sessionId = await spawnOrchestrator(projectId, true);
+		const sessionId = await spawnOrchestrator(projectId, "restart", true);
 		await refreshWorkspaceState(queryClient);
 		void navigate({
 			to: "/projects/$projectId/sessions/$sessionId",
diff --git a/frontend/src/renderer/lib/spawn-orchestrator.test.ts b/frontend/src/renderer/lib/spawn-orchestrator.test.ts
index a8748fd20..2d547fadd 100644
--- a/frontend/src/renderer/lib/spawn-orchestrator.test.ts
+++ b/frontend/src/renderer/lib/spawn-orchestrator.test.ts
@@ -1,6 +1,7 @@
 import { describe, expect, it, vi, beforeEach } from "vitest";
 import { spawnOrchestrator } from "./spawn-orchestrator";
 import { apiClient } from "./api-client";
+import { captureRendererEvent } from "./telemetry";
 
 vi.mock("./api-client", () => ({
 	apiClient: { POST: vi.fn() },
@@ -14,6 +15,12 @@ vi.mock("./api-client", () => ({
 	},
 }));
 
+vi.mock("./telemetry", () => ({
+	captureRendererEvent: vi.fn().mockResolvedValue(undefined),
+}));
+
+const captureMock = vi.mocked(captureRendererEvent);
+
 describe("spawnOrchestrator", () => {
 	beforeEach(() => vi.clearAllMocks());
 
@@ -23,7 +30,7 @@ describe("spawnOrchestrator", () => {
 			error: undefined,
 			response: { status: 201 },
 		});
-		const id = await spawnOrchestrator("proj", true);
+		const id = await spawnOrchestrator("proj", "restore_dialog", true);
 		expect(id).toBe("proj-9");
 		expect(apiClient.POST).toHaveBeenCalledWith("/api/v1/orchestrators", {
 			body: { projectId: "proj", clean: true },
@@ -36,12 +43,43 @@ describe("spawnOrchestrator", () => {
 			error: undefined,
 			response: { status: 201 },
 		});
-		await spawnOrchestrator("proj");
+		await spawnOrchestrator("proj", "board");
 		expect(apiClient.POST).toHaveBeenCalledWith("/api/v1/orchestrators", {
 			body: { projectId: "proj", clean: false },
 		});
 	});
 
+	it("emits the requested + succeeded triad keyed by source", async () => {
+		(apiClient.POST as ReturnType<typeof vi.fn>).mockResolvedValue({
+			data: { orchestrator: { id: "proj-7" } },
+			error: undefined,
+			response: { status: 201 },
+		});
+		await spawnOrchestrator("proj", "sidebar");
+		expect(captureMock).toHaveBeenCalledWith("ao.renderer.orchestrator_spawn_requested", {
+			project_id: "proj",
+			source: "sidebar",
+		});
+		expect(captureMock).toHaveBeenCalledWith("ao.renderer.orchestrator_spawn_succeeded", {
+			project_id: "proj",
+			source: "sidebar",
+		});
+	});
+
+	it("emits the failed event and rethrows when the daemon rejects the spawn", async () => {
+		(apiClient.POST as ReturnType<typeof vi.fn>).mockResolvedValue({
+			data: undefined,
+			error: { message: "boom" },
+			response: { status: 500 },
+		});
+		await expect(spawnOrchestrator("proj", "topbar")).rejects.toThrow("boom");
+		expect(captureMock).toHaveBeenCalledWith("ao.renderer.orchestrator_spawn_failed", {
+			project_id: "proj",
+			source: "topbar",
+		});
+		expect(captureMock).not.toHaveBeenCalledWith("ao.renderer.orchestrator_spawn_succeeded", expect.anything());
+	});
+
 	it("surfaces daemon spawn error messages and codes", async () => {
 		(apiClient.POST as ReturnType<typeof vi.fn>).mockResolvedValue({
 			data: undefined,
@@ -49,6 +87,8 @@ describe("spawnOrchestrator", () => {
 			response: { status: 400 },
 		});
 
-		await expect(spawnOrchestrator("proj")).rejects.toThrow("agent binary not found on PATH (AGENT_BINARY_NOT_FOUND)");
+		await expect(spawnOrchestrator("proj", "board")).rejects.toThrow(
+			"agent binary not found on PATH (AGENT_BINARY_NOT_FOUND)",
+		);
 	});
 });
diff --git a/frontend/src/renderer/lib/spawn-orchestrator.ts b/frontend/src/renderer/lib/spawn-orchestrator.ts
index 13d2f5533..c1be2ad62 100644
--- a/frontend/src/renderer/lib/spawn-orchestrator.ts
+++ b/frontend/src/renderer/lib/spawn-orchestrator.ts
@@ -1,19 +1,46 @@
 import { apiClient, apiErrorMessage } from "./api-client";
+import { captureRendererEvent } from "./telemetry";
+
+// Every UI entry point that spawns an orchestrator: the board CTA, the topbar
+// and sidebar launchers, the restore-unavailable dialog, and the auto-spawn
+// right after a project is added. Emitting the triad from inside
+// spawnOrchestrator (keyed by source) guarantees each path reports, instead of
+// each call site remembering to instrument itself. Keep in sync with the
+// allowed-source list in telemetry.ts.
+export type OrchestratorSpawnSource =
+	| "board"
+	| "restore_dialog"
+	| "topbar"
+	| "sidebar"
+	| "project_add"
+	| "settings"
+	| "restart";
 
 /** Spawn the project's orchestrator session via the daemon API. When clean is
  *  true the daemon first tears down any active orchestrator for the project, then
  *  re-spawns one on the canonical branch (reattaching the existing branch). */
-export async function spawnOrchestrator(projectId: string, clean = false): Promise<string> {
-	const { data, error, response } = await apiClient.POST("/api/v1/orchestrators", {
-		body: { projectId, clean },
-	});
+export async function spawnOrchestrator(
+	projectId: string,
+	source: OrchestratorSpawnSource,
+	clean = false,
+): Promise<string> {
+	void captureRendererEvent("ao.renderer.orchestrator_spawn_requested", { project_id: projectId, source });
+	try {
+		const { data, error, response } = await apiClient.POST("/api/v1/orchestrators", {
+			body: { projectId, clean },
+		});
 
-	if (error || !data?.orchestrator?.id) {
-		const message = error
-			? apiErrorMessage(error, `Failed to spawn orchestrator (${response.status})`)
-			: `Failed to spawn orchestrator (${response.status})`;
-		throw new Error(message);
+		if (error || !data?.orchestrator?.id) {
+			const message = error
+				? apiErrorMessage(error, `Failed to spawn orchestrator (${response.status})`)
+				: `Failed to spawn orchestrator (${response.status})`;
+			throw new Error(message);
+		}
+
+		void captureRendererEvent("ao.renderer.orchestrator_spawn_succeeded", { project_id: projectId, source });
+		return data.orchestrator.id;
+	} catch (err) {
+		void captureRendererEvent("ao.renderer.orchestrator_spawn_failed", { project_id: projectId, source });
+		throw err;
 	}
-
-	return data.orchestrator.id;
 }
diff --git a/frontend/src/renderer/lib/telemetry.test.ts b/frontend/src/renderer/lib/telemetry.test.ts
index 34e70d9e3..b14cb1cf5 100644
--- a/frontend/src/renderer/lib/telemetry.test.ts
+++ b/frontend/src/renderer/lib/telemetry.test.ts
@@ -111,4 +111,95 @@ describe("telemetry sanitizers", () => {
 			"https://api.example.com/endpoint",
 		);
 	});
+
+	it("hashes project ids and drops everything else on CTA triads", async () => {
+		const triads = [
+			"ao.renderer.task_create_requested",
+			"ao.renderer.task_create_succeeded",
+			"ao.renderer.task_create_failed",
+			"ao.renderer.session_kill_requested",
+			"ao.renderer.session_kill_succeeded",
+			"ao.renderer.session_kill_failed",
+			"ao.renderer.settings_save_requested",
+			"ao.renderer.settings_save_succeeded",
+			"ao.renderer.settings_save_failed",
+		];
+		for (const event of triads) {
+			const props = await sanitizeRendererProperties(event, {
+				project_id: "demo-project",
+				title: "raw user text",
+				error: "raw error with /Users/alice/path",
+			});
+			expect(Object.keys(props)).toEqual(["project_id_hash"]);
+		}
+	});
+
+	it("keeps only the source enum on orchestrator_spawn events", async () => {
+		const props = await sanitizeRendererProperties("ao.renderer.orchestrator_spawn_requested", {
+			project_id: "demo-project",
+			source: "board",
+		});
+		expect(Object.keys(props).sort()).toEqual(["project_id_hash", "source"]);
+		expect(props.source).toBe("board");
+
+		const badSource = await sanitizeRendererProperties("ao.renderer.orchestrator_spawn_failed", {
+			project_id: "demo-project",
+			source: "/Users/alice/private",
+		});
+		expect(badSource).not.toHaveProperty("source");
+	});
+
+	it("keeps every whitelisted spawn source, including topbar/sidebar/project_add/settings/restart", async () => {
+		for (const source of ["board", "restore_dialog", "topbar", "sidebar", "project_add", "settings", "restart"]) {
+			const props = await sanitizeRendererProperties("ao.renderer.orchestrator_spawn_succeeded", {
+				project_id: "demo-project",
+				source,
+			});
+			expect(Object.keys(props).sort()).toEqual(["project_id_hash", "source"]);
+			expect(props.source).toBe(source);
+		}
+	});
+
+	it("keeps only enum values on notification events", async () => {
+		expect(await sanitizeRendererProperties("ao.renderer.notification_opened", { target: "pr" })).toEqual({
+			target: "pr",
+		});
+		expect(await sanitizeRendererProperties("ao.renderer.notification_opened", { target: "http://x" })).toEqual({});
+		expect(await sanitizeRendererProperties("ao.renderer.notification_marked_read", { scope: "all" })).toEqual({
+			scope: "all",
+		});
+		expect(await sanitizeRendererProperties("ao.renderer.notification_marked_read", { scope: "everything" })).toEqual(
+			{},
+		);
+	});
+
+	it("whitelists coarse daemon failure fields and drops messages", async () => {
+		const props = await sanitizeRendererProperties("ao.renderer.daemon_failure", {
+			daemon_state: "error",
+			code: "spawn_failed",
+			exit_code: 1,
+			signal: "SIGKILL",
+			message: "spawn /Users/alice/ao failed",
+		});
+		expect(props).toEqual({ daemon_state: "error", code: "spawn_failed", exit_code: 1, signal: "SIGKILL" });
+	});
+
+	it("whitelists normalized api_error fields", async () => {
+		const props = await sanitizeRendererProperties("ao.renderer.api_error", {
+			operation: "GET /api/v1/projects/:id",
+			error_category: "http_5xx",
+			status: 500,
+			body: "raw response body",
+		});
+		expect(props).toEqual({ operation: "GET /api/v1/projects/:id", error_category: "http_5xx", status: 500 });
+	});
+
+	it("keeps only the reason enum on terminal_attach_failed", async () => {
+		expect(await sanitizeRendererProperties("ao.renderer.terminal_attach_failed", { reason: "open_timeout" })).toEqual({
+			reason: "open_timeout",
+		});
+		expect(
+			await sanitizeRendererProperties("ao.renderer.terminal_attach_failed", { reason: "something else" }),
+		).toEqual({});
+	});
 });
diff --git a/frontend/src/renderer/lib/telemetry.ts b/frontend/src/renderer/lib/telemetry.ts
index 100c290b5..e71f0bdbb 100644
--- a/frontend/src/renderer/lib/telemetry.ts
+++ b/frontend/src/renderer/lib/telemetry.ts
@@ -128,6 +128,19 @@ async function sanitizeRendererContextProperties(properties?: TelemetryPropertie
 	return safe;
 }
 
+// Allowed `source` enum for the orchestrator-spawn triad. Kept as a literal set
+// here (rather than imported from spawn-orchestrator.ts, which imports this
+// module) to avoid a cycle; keep in sync with OrchestratorSpawnSource.
+const ORCHESTRATOR_SPAWN_SOURCES = new Set([
+	"board",
+	"restore_dialog",
+	"topbar",
+	"sidebar",
+	"project_add",
+	"settings",
+	"restart",
+]);
+
 export async function sanitizeRendererProperties(
 	event: string,
 	properties?: TelemetryProperties,
@@ -147,11 +160,52 @@ export async function sanitizeRendererProperties(
 			break;
 		case "ao.renderer.project_add_succeeded":
 		case "ao.renderer.project_removed":
-		case "ao.renderer.orchestrator_open_requested": {
+		case "ao.renderer.orchestrator_open_requested":
+		case "ao.renderer.task_create_requested":
+		case "ao.renderer.task_create_succeeded":
+		case "ao.renderer.task_create_failed":
+		case "ao.renderer.session_kill_requested":
+		case "ao.renderer.session_kill_succeeded":
+		case "ao.renderer.session_kill_failed":
+		case "ao.renderer.settings_save_requested":
+		case "ao.renderer.settings_save_succeeded":
+		case "ao.renderer.settings_save_failed": {
 			const projectIDHash = await hashedTelemetryID(properties?.project_id);
 			if (projectIDHash) safe.project_id_hash = projectIDHash;
 			break;
 		}
+		case "ao.renderer.orchestrator_spawn_requested":
+		case "ao.renderer.orchestrator_spawn_succeeded":
+		case "ao.renderer.orchestrator_spawn_failed": {
+			const projectIDHash = await hashedTelemetryID(properties?.project_id);
+			if (projectIDHash) safe.project_id_hash = projectIDHash;
+			if (typeof properties?.source === "string" && ORCHESTRATOR_SPAWN_SOURCES.has(properties.source)) {
+				safe.source = properties.source;
+			}
+			break;
+		}
+		case "ao.renderer.notification_opened":
+			if (properties?.target === "pr" || properties?.target === "session") safe.target = properties.target;
+			break;
+		case "ao.renderer.notification_marked_read":
+			if (properties?.scope === "single" || properties?.scope === "all") safe.scope = properties.scope;
+			break;
+		case "ao.renderer.daemon_failure":
+			if (typeof properties?.daemon_state === "string") safe.daemon_state = properties.daemon_state;
+			if (typeof properties?.code === "string") safe.code = properties.code;
+			if (typeof properties?.exit_code === "number") safe.exit_code = properties.exit_code;
+			if (typeof properties?.signal === "string") safe.signal = properties.signal;
+			break;
+		case "ao.renderer.api_error":
+			if (typeof properties?.operation === "string") safe.operation = properties.operation;
+			if (typeof properties?.error_category === "string") safe.error_category = properties.error_category;
+			if (typeof properties?.status === "number") safe.status = properties.status;
+			break;
+		case "ao.renderer.terminal_attach_failed":
+			if (properties?.reason === "open_timeout" || properties?.reason === "pane_error") {
+				safe.reason = properties.reason;
+			}
+			break;
 	}
 	return safe;
 }
diff --git a/frontend/src/renderer/main.tsx b/frontend/src/renderer/main.tsx
index 48ce485a3..a575674db 100644
--- a/frontend/src/renderer/main.tsx
+++ b/frontend/src/renderer/main.tsx
@@ -8,9 +8,11 @@ import { queryClient } from "./lib/query-client";
 import { createAppRouter } from "./router";
 import { TelemetryBoundary } from "./components/TelemetryBoundary";
 import { initTelemetry } from "./lib/telemetry";
+import { startDaemonFailureTelemetry } from "./lib/daemon-telemetry";
 
 const router = createAppRouter(queryClient);
 void initTelemetry();
+startDaemonFailureTelemetry();
 
 declare module "@tanstack/react-router" {
 	interface Register {
diff --git a/frontend/src/renderer/routes/_shell.tsx b/frontend/src/renderer/routes/_shell.tsx
index 8891662b2..9e176122d 100644
--- a/frontend/src/renderer/routes/_shell.tsx
+++ b/frontend/src/renderer/routes/_shell.tsx
@@ -112,7 +112,7 @@ function ShellLayout() {
 			void captureRendererEvent("ao.renderer.project_add_succeeded", { project_id: workspace.id });
 			updateWorkspaces((current) => [workspace, ...current.filter((item) => item.id !== workspace.id)]);
 			try {
-				const sessionId = await spawnOrchestrator(workspace.id);
+				const sessionId = await spawnOrchestrator(workspace.id, "project_add");
 				await queryClient.invalidateQueries({ queryKey: workspaceQueryKey });
 				void navigate({
 					to: "/projects/$projectId/sessions/$sessionId",
diff --git a/frontend/src/shared/daemon-attach.test.ts b/frontend/src/shared/daemon-attach.test.ts
index 12dba66fd..66da84ccc 100644
--- a/frontend/src/shared/daemon-attach.test.ts
+++ b/frontend/src/shared/daemon-attach.test.ts
@@ -174,6 +174,7 @@ describe("resolveDaemonFromRunFile", () => {
 			executablePath: undefined,
 			workingDirectory: undefined,
 			message: "An AO daemon is already running, but it is not ready yet.",
+			code: "not_ready",
 		});
 	});
 
@@ -271,6 +272,7 @@ describe("resolveDaemonFromPort", () => {
 			executablePath: undefined,
 			workingDirectory: undefined,
 			message: "An AO daemon is already running, but it is not ready yet.",
+			code: "not_ready",
 		});
 	});
 
diff --git a/frontend/src/shared/daemon-attach.ts b/frontend/src/shared/daemon-attach.ts
index 31bc702fd..8298c7e60 100644
--- a/frontend/src/shared/daemon-attach.ts
+++ b/frontend/src/shared/daemon-attach.ts
@@ -147,6 +147,7 @@ async function readinessStatus(
 			executablePath: health.executablePath,
 			workingDirectory: health.workingDirectory,
 			message: "An AO daemon is already running, but it is not ready yet.",
+			code: "not_ready",
 		};
 	}
 
@@ -159,6 +160,7 @@ async function readinessStatus(
 			executablePath: ready.executablePath,
 			workingDirectory: ready.workingDirectory,
 			message,
+			code: "identity_mismatch",
 		};
 	}
 
diff --git a/frontend/src/shared/daemon-status.ts b/frontend/src/shared/daemon-status.ts
index 4476d6ffd..679ea5ce1 100644
--- a/frontend/src/shared/daemon-status.ts
+++ b/frontend/src/shared/daemon-status.ts
@@ -1,6 +1,19 @@
 // DaemonStatus is the supervisor → renderer handshake payload, shared by the
 // Electron main process (which derives it) and the preload bridge (which types
 // the IPC surface). The renderer picks it up through the preload's AoBridge type.
+// Machine-readable failure classification for telemetry. `message` is
+// human-facing and may contain local paths; `code` is what gets reported.
+// Statuses without a code (normal ready, user-initiated stop) are not failures.
+export type DaemonFailureCode =
+	| "not_configured"
+	| "daemon_unreachable"
+	| "binary_missing"
+	| "spawn_failed"
+	| "exited"
+	| "port_unconfirmed"
+	| "not_ready"
+	| "identity_mismatch";
+
 export type DaemonStatus = {
 	state: "starting" | "ready" | "stopped" | "error";
 	port?: number;
@@ -8,4 +21,7 @@ export type DaemonStatus = {
 	executablePath?: string;
 	workingDirectory?: string;
 	message?: string;
+	code?: DaemonFailureCode;
+	exitCode?: number | null;
+	signal?: string | null;
 };