diff --git a/apps/leaf/src/agent/runMessage/engines/claudeManagedEngine.ts b/apps/leaf/src/agent/runMessage/engines/claudeManagedEngine.ts
index 185edeccb..81471f2fb 100644
--- a/apps/leaf/src/agent/runMessage/engines/claudeManagedEngine.ts
+++ b/apps/leaf/src/agent/runMessage/engines/claudeManagedEngine.ts
@@ -20,6 +20,16 @@ import { createBraintrustLogger } from "../../../providers/braintrust/index.js";
 import type { AgentEngine } from "../types.js";
 
 const client = new Anthropic();
+
+const AUTH_FAILURE_PATTERN =
+	/invalid or expired access token|request failed \(401\)/i;
+const isAutumnAuthFailure = (output: unknown) => {
+	try {
+		return AUTH_FAILURE_PATTERN.test(JSON.stringify(output) ?? "");
+	} catch {
+		return false;
+	}
+};
 // initLogger sets Braintrust's ambient logger so traced()/spans are recorded.
 const braintrustLogger = createBraintrustLogger();
 const braintrustEnabled = Boolean(braintrustLogger);
diff --git a/apps/leaf/src/harness/claudeManaged/repos/claudeManagedRepo.ts b/apps/leaf/src/harness/claudeManaged/repos/claudeManagedRepo.ts
index 77f064206..09ac76ae9 100644
--- a/apps/leaf/src/harness/claudeManaged/repos/claudeManagedRepo.ts
+++ b/apps/leaf/src/harness/claudeManaged/repos/claudeManagedRepo.ts
@@ -113,6 +113,22 @@ export const cmaRepo = {
 		return row;
 	},
 
+	// Forces the next ensureAutumnVault to resync tokens into the vault.
+	markVaultStale: async ({
+		db,
+		env,
+		orgId,
+	}: {
+		db: ChatDb;
+		env: AppEnv;
+		orgId: string;
+	}) => {
+		await db
+			.update(cmaVaults)
+			.set({ updated_at: 0 })
+			.where(and(eq(cmaVaults.org_id, orgId), eq(cmaVaults.env, env)));
+	},
+
 	upsertVault: async ({
 		credentialId,
 		db,
diff --git a/apps/leaf/src/ui/blocks.ts b/apps/leaf/src/ui/blocks.ts
index 1a3ad6905..9325661a8 100644
--- a/apps/leaf/src/ui/blocks.ts
+++ b/apps/leaf/src/ui/blocks.ts
@@ -824,6 +824,7 @@ export const approvalStatusCard = ({
 						),
 					]
 				: []),
+			...(config ? [CardText(config, { style: "muted" })] : []),
 		],
 	});
 };
diff --git a/apps/leaf/src/ui/previewContent.ts b/apps/leaf/src/ui/previewContent.ts
new file mode 100644
index 000000000..07b4a12a0
--- /dev/null
+++ b/apps/leaf/src/ui/previewContent.ts
@@ -0,0 +1,185 @@
+import type { CardChild } from "chat";
+import { CardText, Table } from "chat";
+import { format } from "date-fns";
+
+type LooseRecord = Record<string, unknown>;
+
+const MAX_LINE_ITEM_ROWS = 10;
+
+const asRecord = (value: unknown): LooseRecord | null =>
+	value && typeof value === "object" && !Array.isArray(value)
+		? (value as LooseRecord)
+		: null;
+
+const parseJson = (text: string): unknown => {
+	try {
+		return JSON.parse(text);
+	} catch {
+		return null;
+	}
+};
+
+export const formatEpochDate = (epochMs: number) =>
+	format(epochMs, "MMM d, yyyy");
+
+// Amounts are major currency units (the schema's "in cents" wording is stale —
+// the dashboard renders these values directly).
+const formatMoney = (amount: number, currency: string) => {
+	try {
+		return new Intl.NumberFormat("en-US", {
+			currency: currency.toUpperCase(),
+			currencyDisplay: "narrowSymbol",
+			style: "currency",
+		}).format(amount);
+	} catch {
+		return `$${amount.toFixed(2)}`;
+	}
+};
+
+// Unwraps MCP transport shapes around the preview payload: JSON strings,
+// [{text}] content arrays, {content} results, and the {preview, pending} wrapper.
+export const parsePreviewPayload = (preview: unknown): LooseRecord | null => {
+	if (typeof preview === "string") {
+		const parsed = parseJson(preview.trim());
+		return parsed ? parsePreviewPayload(parsed) : null;
+	}
+	if (Array.isArray(preview)) {
+		for (const entry of preview) {
+			const record = asRecord(entry);
+			if (typeof record?.text !== "string") continue;
+			const parsed = parsePreviewPayload(record.text);
+			if (parsed) return parsed;
+		}
+		return null;
+	}
+	const record = asRecord(preview);
+	if (!record) return null;
+	if (Array.isArray(record.content)) return parsePreviewPayload(record.content);
+	if ("preview" in record) return parsePreviewPayload(record.preview);
+	return record;
+};
+
+const UPDATE_INTENT_LABELS: Record<string, string> = {
+	cancel_end_of_cycle: "Cancel at end of cycle",
+	cancel_immediately: "Cancel immediately",
+	uncancel: "Uncancel",
+	update_plan: "Update plan",
+	update_quantity: "Update quantity",
+};
+
+const lineItemRows = ({
+	lineItems,
+	currency,
+}: {
+	lineItems: unknown[];
+	currency: string;
+}) => {
+	const items = lineItems.flatMap((item) => {
+		const record = asRecord(item);
+		return typeof record?.display_name === "string" &&
+			typeof record.total === "number"
+			? [{ name: record.display_name, total: record.total }]
+			: [];
+	});
+
+	const rows = items
+		.slice(0, MAX_LINE_ITEM_ROWS)
+		.map((item) => [item.name, formatMoney(item.total, currency)]);
+	if (items.length > MAX_LINE_ITEM_ROWS) {
+		rows.push([`+${items.length - MAX_LINE_ITEM_ROWS} more items`, ""]);
+	}
+	return rows;
+};
+
+// attach / createSchedule / updateSubscription previews all share the
+// BillingPreviewResponse shape (line_items, total, currency, next_cycle).
+// Rendered receipt-style: one table holding line items AND total rows.
+const billingPreviewElements = (payload: LooseRecord): CardChild[] => {
+	const currency =
+		typeof payload.currency === "string" ? payload.currency : "usd";
+	const rows = lineItemRows({
+		lineItems: payload.line_items as unknown[],
+		currency,
+	});
+
+	const nextCycle = asRecord(payload.next_cycle);
+	const intentLabel =
+		typeof payload.intent === "string"
+			? UPDATE_INTENT_LABELS[payload.intent]
+			: undefined;
+
+	rows.push(["Due now", formatMoney(payload.total as number, currency)]);
+	if (
+		typeof nextCycle?.total === "number" &&
+		typeof nextCycle.starts_at === "number"
+	) {
+		rows.push([
+			`Next cycle · ${formatEpochDate(nextCycle.starts_at)}`,
+			formatMoney(nextCycle.total, currency),
+		]);
+	}
+
+	const notes = [
+		intentLabel ? `Change: ${intentLabel}` : null,
+		payload.redirect_to_checkout === true
+			? "Customer pays via checkout link"
+			: null,
+	].filter((note): note is string => Boolean(note));
+
+	return [
+		Table({ align: ["left", "right"], headers: ["Item", "Amount"], rows }),
+		...(notes.length
+			? [CardText(notes.join("  ·  "), { style: "muted" })]
+			: []),
+	];
+};
+
+const balancePreviewElements = (payload: LooseRecord): CardChild[] | null => {
+	const request = asRecord(payload.request);
+	if (!request) return null;
+
+	const reset = asRecord(request.reset);
+	const fields = [
+		["Feature", request.feature_id],
+		[
+			"Grant",
+			request.unlimited === true ? "Unlimited" : request.included_grant,
+		],
+		[
+			"Expires",
+			typeof request.expires_at === "number"
+				? formatEpochDate(request.expires_at)
+				: null,
+		],
+		[
+			"Resets",
+			typeof reset?.interval === "string"
+				? `Every ${typeof reset.interval_count === "number" && reset.interval_count > 1 ? `${reset.interval_count} ${reset.interval}s` : reset.interval}`
+				: null,
+		],
+	].flatMap(([label, value]) =>
+		typeof value === "string" || typeof value === "number"
+			? [`**${label}**  ${value}`]
+			: [],
+	);
+
+	return [
+		...(fields.length ? [CardText(fields.join("\n"))] : []),
+		...(typeof payload.impact === "string"
+			? [CardText(payload.impact, { style: "muted" })]
+			: []),
+	];
+};
+
+/** Structured card body for a preview payload, or null to fall back to text. */
+export const previewElements = (preview: unknown): CardChild[] | null => {
+	const payload = parsePreviewPayload(preview);
+	if (!payload) return null;
+	if (Array.isArray(payload.line_items) && typeof payload.total === "number") {
+		return billingPreviewElements(payload);
+	}
+	if (payload.action === "createBalance") {
+		return balancePreviewElements(payload);
+	}
+	return null;
+};
diff --git a/apps/leaf/tests/unit/ui/previewContent.test.ts b/apps/leaf/tests/unit/ui/previewContent.test.ts
new file mode 100644
index 000000000..76bf9ba6a
--- /dev/null
+++ b/apps/leaf/tests/unit/ui/previewContent.test.ts
@@ -0,0 +1,157 @@
+import { describe, expect, test } from "bun:test";
+import { approvalCard } from "../../../src/ui/blocks.js";
+import {
+	parsePreviewPayload,
+	previewElements,
+} from "../../../src/ui/previewContent.js";
+
+const attachPreview = {
+	object: "attach_preview",
+	customer_id: "cus_1",
+	currency: "usd",
+	line_items: [
+		{
+			display_name: "Pro Checkout",
+			description: "Pro Checkout - Base Price",
+			subtotal: 20,
+			total: 20,
+			discounts: [],
+		},
+		{
+			display_name: "Messages",
+			description: "Prepaid usage",
+			subtotal: 5.5,
+			total: 5.5,
+			discounts: [],
+		},
+	],
+	subtotal: 25.5,
+	total: 25.5,
+	next_cycle: { starts_at: 1812731225000, subtotal: 40, total: 40 },
+	redirect_to_checkout: false,
+};
+
+describe("parsePreviewPayload", () => {
+	test("unwraps MCP content arrays of JSON text", () => {
+		const payload = parsePreviewPayload([
+			{ type: "text", text: JSON.stringify(attachPreview) },
+		]);
+		expect(payload?.customer_id).toBe("cus_1");
+	});
+
+	test("unwraps the agent {preview, pending} wrapper", () => {
+		const payload = parsePreviewPayload({
+			preview: attachPreview,
+			pending: true,
+			message: "Preview ready",
+		});
+		expect(payload?.object).toBe("attach_preview");
+	});
+
+	test("returns null for model prose", () => {
+		expect(parsePreviewPayload("I'll preview this now!")).toBeNull();
+	});
+});
+
+describe("previewElements", () => {
+	test("renders billing previews as a line item table with totals", () => {
+		const elements = previewElements(attachPreview);
+		const json = JSON.stringify(elements);
+
+		expect(elements?.[0]?.type).toBe("table");
+		expect(json).toContain("Pro Checkout");
+		expect(json).toContain("$20.00");
+		expect(json).toContain("$5.50");
+		expect(json).toContain("Due now");
+		expect(json).toContain("Next cycle");
+		expect(json).toContain("$40.00");
+	});
+
+	test("labels update subscription intents", () => {
+		const json = JSON.stringify(
+			previewElements({
+				...attachPreview,
+				object: "update_subscription_preview",
+				intent: "cancel_end_of_cycle",
+			}),
+		);
+		expect(json).toContain("Cancel at end of cycle");
+	});
+
+	test("renders createBalance local previews as fields", () => {
+		const json = JSON.stringify(
+			previewElements({
+				action: "createBalance",
+				request: {
+					customer_id: "cus_1",
+					feature_id: "credits",
+					included_grant: 500,
+					expires_at: 1812731225000,
+				},
+				impact: "Creates a standalone balance grant.",
+			}),
+		);
+		expect(json).toContain("credits");
+		expect(json).toContain("500");
+		expect(json).toContain("Expires");
+		expect(json).toContain("standalone balance grant");
+	});
+});
+
+describe("approvalCard with structured previews", () => {
+	test("uses the structured renderer instead of text scraping", () => {
+		const card = approvalCard({
+			id: "approval_1",
+			toolName: "attach",
+			toolArgs: { request: { customer_id: "cus_1", plan_id: "pro" } },
+			preview: attachPreview,
+		});
+		const json = JSON.stringify(card);
+
+		expect(json).toContain("table");
+		expect(json).toContain("Due now");
+		expect(card.children.at(-1)?.type).toBe("actions");
+	});
+
+	test("moves environment to subtitle and config to a muted line", () => {
+		const card = approvalCard({
+			id: "approval_1",
+			env: "sandbox" as never,
+			toolName: "attach",
+			toolArgs: {
+				request: {
+					customer_id: "cus_1",
+					plan_id: "pro",
+					redirect_mode: "if_required",
+					invoice_mode: { enabled: true, finalize: false },
+				},
+			},
+			preview: attachPreview,
+		});
+
+		expect(card.subtitle).toContain("Sandbox");
+		const muted = card.children.filter(
+			(child) => child.type === "text" && child.style === "muted",
+		);
+		const mutedJson = JSON.stringify(muted);
+		expect(mutedJson).toContain("Redirect: if_required");
+		expect(mutedJson).toContain("Invoice: enabled, draft invoice");
+		expect(JSON.stringify(card.children)).not.toContain("Environment");
+	});
+
+	test("shows schedule start dates from tool args", () => {
+		const card = approvalCard({
+			id: "approval_2",
+			toolName: "createSchedule",
+			toolArgs: {
+				request: {
+					customer_id: "cus_1",
+					plan_id: "pro",
+					starts_at: 1812731225000,
+				},
+			},
+			preview: attachPreview,
+		});
+		expect(JSON.stringify(card)).toContain("Starts");
+	});
+});