fix(tunnel): break the expired-leaf renewal deadlock

`POST /renew` is authenticated by mTLS with the very leaf it renews, so once that leaf lapsed the host could never renew it and the tunnel stayed down until an operator re-paired by hand. Production hit exactly this: the Mac slept through its 8h renewal window, the 24h leaf expired, and the agent then logged `client certificate has expired; renew before dialling` 6380 times over 8 days without recovering. Three layers independently refused an expired leaf, so all three had to move: - agent `buildTlsOptions` gains an opt-in `expiredGraceMs`. Absent/0 keeps the historical fail-closed behaviour, and the TUNNEL dial never passes it — only the renew transport does. Past the window it throws the new `CertExpiredBeyondGraceError`. - agent rotator routes an already-expired leaf to a separate recovery endpoint and treats "beyond grace" as TERMINAL: report once via `onExhausted`, stop retrying, and name the fix (re-pair) instead of spamming warnings forever. - control-plane `assertPresentedCertTrusted` grants a bounded grace on `notAfter` only. Chain validation, SPIFFE identity, `notBefore`, and the registry `active`/account checks are all unchanged, so revocation still bites. - new `deploy/nginx/recover-mtls.conf` (:8472). The strict enroll vhost cannot host this: under `ssl_verify_client optional` nginx answers a bare 400 as soon as a presented cert fails verification, so an expired leaf never reaches the location — and the directive is server-level, not per-location. Grace defaults to 30 days on both ends and is configurable (`RECOVER_URL`, `expiredRenewGraceMs`). The honest trade is recorded in the code: a stale stolen leaf stays reusable for the window, which widens an existing exposure (an unexpired stolen leaf already renews indefinitely) rather than opening a new one. Verified: agent 296/296, control-plane 286/286, tsc clean on both.
2026-07-29 09:41:03 +02:00
parent b1bc50ccd1
commit f3f4d8baa6
11 changed files with 643 additions and 16 deletions
--- a/agent/src/certs/nativeRenew.ts
+++ b/agent/src/certs/nativeRenew.ts
@@ -22,7 +22,12 @@ import type { Keystore } from '../keys/keystore.js'
 import type { Logger } from '../log/logger.js'
 import type { TimerLike } from '../transport/seams.js'
 import { createBackoff } from '../transport/backoff.js'
-import { buildTlsOptions, type CertParser, type TlsClientOptions } from '../transport/dial.js'
+import {
+  buildTlsOptions,
+  DEFAULT_EXPIRED_RENEW_GRACE_MS,
+  type CertParser,
+  type TlsClientOptions,
+} from '../transport/dial.js'
 import { DEFAULT_CERT_RENEW_WINDOW_MS } from '../health/probe.js'
 import { createCertRotator, type CertRotator } from './rotation.js'

@@ -126,7 +131,7 @@ function toHeaderRecord(headers: RequestInit['headers']): Record<string, string>
 */
 export function createMtlsFetch(
  ks: Keystore,
-  opts: { request?: MtlsRequest; certParser?: CertParser } = {},
+  opts: { request?: MtlsRequest; certParser?: CertParser; expiredGraceMs?: number } = {},
 ): typeof fetch {
  const request = opts.request ?? defaultMtlsRequest
  const shim = async (input: Parameters<typeof fetch>[0], init?: RequestInit): Promise<Response> => {
@@ -135,7 +140,14 @@ export function createMtlsFetch(
    // SYSTEM roots — its host (the LE-fronted control-plane) is publicly trusted; pinning the private
    // enroll caChain here fails with "unable to get local issuer certificate". So drop `ca` (absent →
    // node uses the default roots); rejectUnauthorized stays true.
-    const full = buildTlsOptions(ks, { ...(opts.certParser ? { certParser: opts.certParser } : {}) })
+    // This transport exists ONLY to renew, so it opts into the expired-leaf grace: refusing here is
+    // exactly the deadlock we are fixing (mTLS renew needs the very leaf that lapsed). Past the
+    // window `buildTlsOptions` throws CertExpiredBeyondGraceError, which the rotator treats as
+    // terminal rather than retrying forever.
+    const full = buildTlsOptions(ks, {
+      expiredGraceMs: opts.expiredGraceMs ?? DEFAULT_EXPIRED_RENEW_GRACE_MS,
+      ...(opts.certParser ? { certParser: opts.certParser } : {}),
+    })
    const tls: TlsClientOptions = { cert: full.cert, key: full.key, rejectUnauthorized: full.rejectUnauthorized }
    const reqInit: MtlsRequestInit = {
      method: init?.method ?? 'GET',
@@ -195,6 +207,16 @@ export function wireAutoRenew(
      error: errorMessage(err),
    })
  })
+  // Terminal: the grace window is spent, so every further attempt is guaranteed to fail. Say so once,
+  // at error level, naming the fix — and deliberately do NOT stop the supervisor: `pair` writes fresh
+  // cert files that the restart-on-exit frpc child picks up without a manual service restart.
+  rotator.onExhausted((err) => {
+    logger.log('error', 'frp-client cert expired beyond renewal grace — run `web-terminal-agent pair <CODE>` to re-pair this host', {
+      ...meta,
+      expiredForMs: err.expiredForMs,
+      graceMs: err.graceMs,
+    })
+  })
  rotator.start()
  return { stop: () => rotator.stop() }
 }
@@ -205,6 +227,8 @@ export function wireAutoRenew(
 export interface NativeAutoRenewOpts {
  readonly mtlsRequest?: MtlsRequest
  readonly certParser?: CertParser
+  /** Window in which an already-expired leaf may still authenticate its own renewal. */
+  readonly expiredGraceMs?: number
  readonly timer?: TimerLike
  readonly renewBeforeMs?: number
  readonly retryBaseMs?: number
@@ -232,6 +256,7 @@ export function startNativeAutoRenew(
  const fetchImpl = createMtlsFetch(ks, {
    ...(opts.mtlsRequest ? { request: opts.mtlsRequest } : {}),
    ...(opts.certParser ? { certParser: opts.certParser } : {}),
+    ...(opts.expiredGraceMs !== undefined ? { expiredGraceMs: opts.expiredGraceMs } : {}),
  })
  const rotator = createCertRotator(cfg, id, ks, {
    fetchImpl,
--- a/agent/src/certs/rotation.ts
+++ b/agent/src/certs/rotation.ts
@@ -14,6 +14,7 @@ import type { AgentIdentity } from '../keys/identity.js'
 import type { Keystore } from '../keys/keystore.js'
 import type { TimerLike } from '../transport/seams.js'
 import { createBackoff, type BackoffPolicy } from '../transport/backoff.js'
+import { CertExpiredBeyondGraceError } from '../transport/dial.js'
 import { buildCsr } from '../enroll/csr.js'
 import { certResponseToPem } from './pem.js'

@@ -26,6 +27,11 @@ export interface CertRotator {
  onRevoked(cb: () => void): void
  /** A renewal attempt failed (network/HTTP, NOT a 403 revoke). The rotator retries with backoff. */
  onError(cb: (err: unknown) => void): void
+  /**
+   * TERMINAL: the leaf expired past the renewal grace window, so no future attempt can succeed. The
+   * rotator has stopped; recovery requires an operator re-pair.
+   */
+  onExhausted(cb: (err: CertExpiredBeyondGraceError) => void): void
 }

 export type RenewOutcome = 'rotated' | 'revoked'
@@ -35,6 +41,36 @@ export function renewalUrlFor(cfg: AgentConfig): string {
  return cfg.enrollUrl.replace(/\/enroll$/, '/renew')
 }

+/** The `enroll.<zone>` label the recovery vhost mirrors as `recover.<zone>`. */
+const ENROLL_LABEL = 'enroll.'
+const RECOVER_LABEL = 'recover.'
+
+/**
+ * Renewal route for an ALREADY-EXPIRED leaf, or null when this deployment has none.
+ *
+ * The normal `/renew` vhost runs `ssl_verify_client optional`, which makes nginx answer a bare
+ * `400 Bad Request` as soon as a presented client cert fails verification — an expired leaf never
+ * reaches the location, so it can never be forwarded to the control-plane. Recovery therefore lives
+ * on a sibling `recover.` vhost running `optional_no_ca`, where nginx forwards the cert unverified
+ * and the control-plane is the sole (and full) verifier: chain → SPIFFE → registry status → bounded
+ * expiry grace. Explicit `cfg.recoverUrl` wins; otherwise it is derived by swapping the `enroll.`
+ * label. A deployment whose enroll host has no `enroll.` label gets null (no recovery configured)
+ * rather than a guessed hostname.
+ */
+export function recoveryRenewalUrlFor(cfg: AgentConfig): string | null {
+  if (cfg.recoverUrl != null && cfg.recoverUrl.length > 0) return cfg.recoverUrl
+  let url: URL
+  try {
+    url = new URL(cfg.enrollUrl)
+  } catch {
+    return null
+  }
+  if (!url.hostname.startsWith(ENROLL_LABEL)) return null
+  url.hostname = RECOVER_LABEL + url.hostname.slice(ENROLL_LABEL.length)
+  url.pathname = url.pathname.replace(/\/enroll$/, '/renew')
+  return url.toString()
+}
+
 /** Ms until (validTo − renewBeforeMs), clamped to ≥ 0. */
 export function computeRenewDelayMs(
  certPem: string,
@@ -56,9 +92,10 @@ export async function renewCert(
  id: AgentIdentity,
  ks: Keystore,
  fetchImpl: typeof fetch,
+  opts: { url?: string } = {},
 ): Promise<RenewOutcome> {
  const csr = buildCsr(id, cfg.subdomain ?? 'web-terminal-agent')
-  const res = await fetchImpl(renewalUrlFor(cfg), {
+  const res = await fetchImpl(opts.url ?? renewalUrlFor(cfg), {
    method: 'POST',
    headers: { 'content-type': 'application/json' },
    body: JSON.stringify({ csr }),
@@ -102,6 +139,7 @@ export function createCertRotator(
  let rotatedCb: (() => void) | null = null
  let revokedCb: (() => void) | null = null
  let errorCb: ((err: unknown) => void) | null = null
+  let exhaustedCb: ((err: CertExpiredBeyondGraceError) => void) | null = null

  function schedule(): void {
    const certs = ks.loadCert()
@@ -110,8 +148,21 @@ export function createCertRotator(
    handle = timer.setTimeout(runRenewal, delay)
  }

+  /**
+   * Pick the endpoint for THIS attempt. A leaf that has already lapsed cannot be forwarded by the
+   * strict vhost, so it must go to the recovery vhost; a still-valid leaf always uses the normal one.
+   * With no recovery endpoint configured we fall back to the normal URL and let it fail honestly.
+   */
+  function endpointForNow(): string {
+    const certs = ks.loadCert()
+    if (certs === null) return renewalUrlFor(cfg)
+    const expired = parseCert(certs.certPem).getTime() < now().getTime()
+    if (!expired) return renewalUrlFor(cfg)
+    return recoveryRenewalUrlFor(cfg) ?? renewalUrlFor(cfg)
+  }
+
  function runRenewal(): void {
-    void renewCert(cfg, id, ks, doFetch)
+    void renewCert(cfg, id, ks, doFetch, { url: endpointForNow() })
      .then((outcome) => {
        if (outcome === 'revoked') {
          revokedCb?.()
@@ -122,6 +173,14 @@ export function createCertRotator(
        schedule()
      })
      .catch((err: unknown) => {
+        // The grace window is spent: no amount of retrying can mint a new leaf, only an operator
+        // re-pair can. Report it ONCE and stop — the old behaviour retried forever and buried the
+        // real signal under thousands of identical warnings.
+        if (err instanceof CertExpiredBeyondGraceError) {
+          handle = null
+          exhaustedCb?.(err)
+          return
+        }
        // Network/HTTP failure (never a 403 revoke): surface it (caller logs, no secret) and retry
        // with backoff. The cert is still valid until expiry, so the tunnel stays up meanwhile — a
        // failed renewal must NEVER tear the supervisor down.
@@ -147,5 +206,8 @@ export function createCertRotator(
    onError(cb): void {
      errorCb = cb
    },
+    onExhausted(cb): void {
+      exhaustedCb = cb
+    },
  }
 }
--- a/agent/src/config/agentConfig.ts
+++ b/agent/src/config/agentConfig.ts
@@ -18,6 +18,13 @@ export interface AgentConfig {
  readonly localTargetUrl: string
  readonly subdomain: string | null
  readonly hostId: string | null
+  /**
+   * Renewal endpoint used ONLY when the current leaf has already expired (the strict `/renew` vhost
+   * rejects an expired client cert before it reaches the control-plane). Optional: when unset it is
+   * derived from `enrollUrl` by swapping the `enroll.` label for `recover.` — see
+   * `certs/rotation.ts` `recoveryRenewalUrlFor`.
+   */
+  readonly recoverUrl?: string | null | undefined
 }

 /**
@@ -59,6 +66,11 @@ export const AgentConfigSchema = z
      .refine(isLoopbackWsUrl, 'localTargetUrl must be a ws:// loopback URL (anti-SSRF)'),
    subdomain: z.string().min(1).nullable(),
    hostId: z.string().min(1).nullable(),
+    recoverUrl: z
+      .string()
+      .refine((u) => hasScheme(u, 'https:'), 'recoverUrl must be an https:// URL')
+      .nullable()
+      .optional(),
  })
  .strict()
  .readonly()
@@ -85,6 +97,7 @@ export function loadAgentConfig(
    localTargetUrl: argv.localTargetUrl ?? env.LOCAL_TARGET_URL ?? DEFAULT_LOCAL_TARGET,
    subdomain: argv.subdomain ?? env.SUBDOMAIN ?? null,
    hostId: argv.hostId ?? env.HOST_ID ?? null,
+    recoverUrl: argv.recoverUrl ?? env.RECOVER_URL ?? null,
  }
  return AgentConfigSchema.parse(merged)
 }
--- a/agent/src/transport/dial.ts
+++ b/agent/src/transport/dial.ts
@@ -21,6 +21,37 @@ export class CertExpiredError extends Error {
  }
 }

+/**
+ * Default window during which an ALREADY-EXPIRED leaf may still authenticate a `/renew` (30 days).
+ *
+ * WHY THIS EXISTS: `/renew` is authenticated by mTLS with the current leaf, so once that leaf lapses
+ * the agent can no longer renew it — a deadlock that bricks the host until a manual re-pair (observed
+ * in production: the leaf expired while the laptop was asleep through its renewal window, then the
+ * agent logged `client certificate has expired; renew before dialling` 6380 times and never
+ * recovered). Accepting a recently-expired leaf ONLY for re-issuance breaks the cycle.
+ *
+ * WHY IT IS SAFE-ENOUGH: the leaf still proves possession of the private key, still has to chain to
+ * the frp-client CA, and the control-plane still refuses a host whose registry status is `revoked` —
+ * none of those checks are relaxed. The delta is that a STALE stolen credential stays reusable for
+ * this window; an attacker holding an UNEXPIRED stolen leaf can already renew indefinitely, so this
+ * widens an existing exposure rather than creating a new class of one. It is bounded, and it never
+ * applies to the tunnel dial — only to re-issuance.
+ */
+export const DEFAULT_EXPIRED_RENEW_GRACE_MS = 30 * 24 * 60 * 60 * 1000
+
+/** The leaf expired so long ago that even the renewal grace is exhausted ⇒ operator must re-pair. */
+export class CertExpiredBeyondGraceError extends Error {
+  constructor(
+    /** How long ago the leaf expired (ms) — non-secret, safe to log. */
+    readonly expiredForMs: number,
+    /** The grace window that was exceeded (ms). */
+    readonly graceMs: number,
+  ) {
+    super('client certificate expired beyond the renewal grace window; re-pair required')
+    this.name = 'CertExpiredBeyondGraceError'
+  }
+}
+
 /** TLS material for the wss client. NOTE: `rejectUnauthorized` is ALWAYS true (anti-MITM). */
 export interface TlsClientOptions {
  readonly cert: string
@@ -44,17 +75,27 @@ const defaultCertParser: CertParser = (pem) => ({ validTo: new Date(new X509Cert
 /**
 * Assemble the mTLS options from the keystore. Throws NotEnrolledError if key/cert are missing,
 * CertExpiredError if the cert is past `validTo`. There is NO token field by construction (INV4).
+ *
+ * `expiredGraceMs` is the ONLY way to get an expired leaf through, and exists solely for the `/renew`
+ * recovery path (see `DEFAULT_EXPIRED_RENEW_GRACE_MS`). Omitted or 0 ⇒ the historical fail-closed
+ * behaviour, unchanged; the tunnel dial deliberately never passes it. Past the window the distinct
+ * `CertExpiredBeyondGraceError` tells the caller to stop retrying and surface "re-pair required".
 */
 export function buildTlsOptions(
  ks: Keystore,
-  opts: { now?: Date; certParser?: CertParser } = {},
+  opts: { now?: Date; certParser?: CertParser; expiredGraceMs?: number } = {},
 ): TlsClientOptions {
  const id = ks.loadIdentity()
  const certs = ks.loadCert()
  if (id === null || certs === null) throw new NotEnrolledError()
  const parse = opts.certParser ?? defaultCertParser
  const now = opts.now ?? new Date()
-  if (parse(certs.certPem).validTo.getTime() < now.getTime()) throw new CertExpiredError()
+  const expiredForMs = now.getTime() - parse(certs.certPem).validTo.getTime()
+  if (expiredForMs > 0) {
+    const graceMs = opts.expiredGraceMs ?? 0
+    if (graceMs <= 0) throw new CertExpiredError()
+    if (expiredForMs > graceMs) throw new CertExpiredBeyondGraceError(expiredForMs, graceMs)
+  }
  return {
    cert: certs.certPem,
    key: id.exportPrivatePkcs8Pem(),
--- a/agent/test/dial.test.ts
+++ b/agent/test/dial.test.ts
@@ -6,7 +6,9 @@ import type { AgentConfig } from '../src/config/agentConfig.js'
 import { generateIdentity } from '../src/keys/identity.js'
 import { openKeystore } from '../src/keys/keystore.js'
 import {
+  CertExpiredBeyondGraceError,
  CertExpiredError,
+  DEFAULT_EXPIRED_RENEW_GRACE_MS,
  NotEnrolledError,
  buildTlsOptions,
  dialRelay,
@@ -65,6 +67,82 @@ describe('buildTlsOptions (T12, INV14/INV4)', () => {
  })
 })

+/**
+ * Expired-leaf RENEWAL grace. The tunnel dial stays fail-closed forever; only the /renew recovery
+ * path may opt in, and only inside a bounded window — otherwise an expired leaf deadlocks the agent
+ * (mTLS renew needs a cert, and the only cert has expired) and the host is bricked until a re-pair.
+ */
+describe('buildTlsOptions expired-renewal grace (deadlock recovery)', () => {
+  const expiredBy = (ms: number) => () => ({ validTo: new Date(Date.now() - ms) })
+  const DAY = 86_400_000
+
+  it('stays fail-closed by DEFAULT — no grace opt-in ⇒ CertExpiredError', () => {
+    const { dir, ks } = enrolledKs()
+    expect(() => buildTlsOptions(ks, { certParser: expiredBy(DAY) })).toThrow(CertExpiredError)
+    rmSync(dir, { recursive: true, force: true })
+  })
+
+  it('expired INSIDE the grace window → returns options so /renew can authenticate', () => {
+    const { dir, ks } = enrolledKs()
+    const tls = buildTlsOptions(ks, {
+      certParser: expiredBy(8 * DAY),
+      expiredGraceMs: DEFAULT_EXPIRED_RENEW_GRACE_MS,
+    })
+    expect(tls.cert).toBe('CERTPEM')
+    expect(tls.rejectUnauthorized).toBe(true)
+    rmSync(dir, { recursive: true, force: true })
+  })
+
+  it('expired BEYOND the grace window → CertExpiredBeyondGraceError (re-pair required)', () => {
+    const { dir, ks } = enrolledKs()
+    expect(() =>
+      buildTlsOptions(ks, {
+        certParser: expiredBy(31 * DAY),
+        expiredGraceMs: DEFAULT_EXPIRED_RENEW_GRACE_MS,
+      }),
+    ).toThrow(CertExpiredBeyondGraceError)
+    rmSync(dir, { recursive: true, force: true })
+  })
+
+  it('grace of 0 is not a bypass — an expired leaf still throws', () => {
+    const { dir, ks } = enrolledKs()
+    expect(() => buildTlsOptions(ks, { certParser: expiredBy(1000), expiredGraceMs: 0 })).toThrow(
+      CertExpiredError,
+    )
+    rmSync(dir, { recursive: true, force: true })
+  })
+
+  it('a still-valid cert is unaffected by the grace option', () => {
+    const { dir, ks } = enrolledKs()
+    const tls = buildTlsOptions(ks, {
+      certParser: future,
+      expiredGraceMs: DEFAULT_EXPIRED_RENEW_GRACE_MS,
+    })
+    expect(tls.cert).toBe('CERTPEM')
+    rmSync(dir, { recursive: true, force: true })
+  })
+
+  it('the TUNNEL dial never gets grace — an expired leaf still refuses to dial', () => {
+    const { dir, ks } = enrolledKs()
+    let constructed = 0
+    class NeverCtor implements RawTlsWs {
+      constructor() {
+        constructed += 1
+      }
+      send(): void {}
+      close(): void {}
+      on(): void {}
+      once(): void {}
+    }
+    // `dialRelay` has no grace seam at all: it fails fast (synchronously) before any socket exists.
+    expect(() =>
+      dialRelay(CFG, ks, { Ctor: NeverCtor as unknown as TlsWsConstructor, certParser: past }),
+    ).toThrow(CertExpiredError)
+    expect(constructed).toBe(0)
+    rmSync(dir, { recursive: true, force: true })
+  })
+})
+
 describe('dialRelay (T12)', () => {
  it('constructs the wss client with the TLS options and resolves on open', async () => {
    const { dir, ks } = enrolledKs()
--- a/agent/test/nativeRenew.test.ts
+++ b/agent/test/nativeRenew.test.ts
@@ -27,6 +27,10 @@ import {
  type MtlsRequest,
 } from '../src/certs/nativeRenew.js'
 import { FakeTimer } from './fixtures/fakes.js'
+import {
+  CertExpiredBeyondGraceError,
+  DEFAULT_EXPIRED_RENEW_GRACE_MS,
+} from '../src/transport/dial.js'

 const CFG: AgentConfig = {
  relayUrl: 'wss://relay/agent',
@@ -109,11 +113,21 @@ describe('createMtlsFetch (A5)', () => {
 describe('wireAutoRenew (A5)', () => {
  function fakeRotator(): {
    rotator: CertRotator
-    fire: { rotated?: () => void; revoked?: () => void; error?: (e: unknown) => void }
+    fire: {
+      rotated?: () => void
+      revoked?: () => void
+      error?: (e: unknown) => void
+      exhausted?: (e: CertExpiredBeyondGraceError) => void
+    }
    start: ReturnType<typeof vi.fn>
    stop: ReturnType<typeof vi.fn>
  } {
-    const fire: { rotated?: () => void; revoked?: () => void; error?: (e: unknown) => void } = {}
+    const fire: {
+      rotated?: () => void
+      revoked?: () => void
+      error?: (e: unknown) => void
+      exhausted?: (e: CertExpiredBeyondGraceError) => void
+    } = {}
    const start = vi.fn()
    const stop = vi.fn()
    const rotator: CertRotator = {
@@ -128,6 +142,9 @@ describe('wireAutoRenew (A5)', () => {
      onError: (cb) => {
        fire.error = cb
      },
+      onExhausted: (cb) => {
+        fire.exhausted = cb
+      },
    }
    return { rotator, fire, start, stop }
  }
@@ -277,3 +294,72 @@ describe('startNativeAutoRenew (A5 end-to-end)', () => {
    rmSync(dir, { recursive: true, force: true })
  })
 })
+
+/**
+ * Expired-leaf recovery. `createMtlsFetch` is the ONE place that decides whether a lapsed leaf may
+ * still be presented; if it keeps refusing (the pre-fix behaviour) the renewal can never leave the
+ * host and the tunnel stays dead until a manual re-pair.
+ */
+describe('createMtlsFetch expired-leaf recovery', () => {
+  const expiredBy = (ms: number) => () => ({ validTo: new Date(Date.now() - ms) })
+  const DAY = 86_400_000
+
+  it('still presents a leaf that expired INSIDE the grace window (renewal can go out)', async () => {
+    const { dir, ks } = enrolledKs()
+    let presented = ''
+    const request: MtlsRequest = async (_url, tls) => {
+      presented = tls.cert
+      return { status: 201, body: '{}' }
+    }
+    const f = createMtlsFetch(ks, { request, certParser: expiredBy(8 * DAY) })
+    const res = await f('https://recover.example.com/renew', { method: 'POST', body: '{}' })
+    expect(res.status).toBe(201)
+    expect(presented).toBe('LEAFCERT')
+    rmSync(dir, { recursive: true, force: true })
+  })
+
+  it('refuses once the leaf is BEYOND the grace window (terminal — re-pair required)', async () => {
+    const { dir, ks } = enrolledKs()
+    const request: MtlsRequest = async () => ({ status: 201, body: '{}' })
+    const f = createMtlsFetch(ks, {
+      request,
+      certParser: expiredBy(DEFAULT_EXPIRED_RENEW_GRACE_MS + DAY),
+    })
+    await expect(f('https://recover.example.com/renew', { method: 'POST' })).rejects.toThrow(
+      CertExpiredBeyondGraceError,
+    )
+    rmSync(dir, { recursive: true, force: true })
+  })
+})
+
+describe('wireAutoRenew exhausted routing', () => {
+  it('logs an actionable re-pair alarm and leaves the supervisor running', () => {
+    const fire: { exhausted?: (e: CertExpiredBeyondGraceError) => void } = {}
+    const rotator: CertRotator = {
+      start: vi.fn(),
+      stop: vi.fn(),
+      onRotated: () => {},
+      onRevoked: () => {},
+      onError: () => {},
+      onExhausted: (cb) => {
+        fire.exhausted = cb
+      },
+    }
+    const restartChild = vi.fn()
+    const stop = vi.fn()
+    const lines: string[] = []
+    wireAutoRenew(rotator, { restartChild, stop }, createLogger('info', (l) => lines.push(l)), {
+      subdomain: 'h7fd8',
+      hostId: 'h-1',
+    })
+    fire.exhausted?.(new CertExpiredBeyondGraceError(40 * 86_400_000, 30 * 86_400_000))
+
+    const alarm = lines.find((l) => /re-pair/i.test(l))
+    expect(alarm).toBeDefined()
+    expect(alarm).toContain('h7fd8')
+    // The supervisor keeps running: a later `pair` writes fresh cert files that the restarting
+    // frpc child picks up. Tearing down here would make recovery need a manual restart too.
+    expect(stop).not.toHaveBeenCalled()
+    expect(restartChild).not.toHaveBeenCalled()
+  })
+})
--- a/agent/test/rotation.test.ts
+++ b/agent/test/rotation.test.ts
@@ -8,9 +8,11 @@ import { openKeystore } from '../src/keys/keystore.js'
 import {
  computeRenewDelayMs,
  createCertRotator,
+  recoveryRenewalUrlFor,
  renewCert,
  renewalUrlFor,
 } from '../src/certs/rotation.js'
+import { CertExpiredBeyondGraceError } from '../src/transport/dial.js'
 import { createBackoff } from '../src/transport/backoff.js'
 import { FakeTimer } from './fixtures/fakes.js'

@@ -159,3 +161,121 @@ describe('createCertRotator (T13)', () => {
    rmSync(dir, { recursive: true, force: true })
  })
 })
+
+/**
+ * Expired-leaf recovery (production deadlock, 2026-07): `/renew` is mTLS-authenticated by the leaf
+ * it renews, so a lapsed leaf can never renew itself. Recovery needs BOTH a different endpoint (the
+ * strict nginx vhost rejects an expired client cert with a bare 400 before any location runs) and a
+ * terminal signal when even the grace window is spent, so the agent stops retrying forever.
+ */
+describe('expired-leaf recovery routing', () => {
+  it('derives the recovery endpoint from an `enroll.` host', () => {
+    expect(recoveryRenewalUrlFor({ ...CFG, enrollUrl: 'https://enroll.terminal.example.com/enroll' })).toBe(
+      'https://recover.terminal.example.com/renew',
+    )
+  })
+
+  it('honours an explicit recoverUrl over the derivation', () => {
+    expect(
+      recoveryRenewalUrlFor({
+        ...CFG,
+        enrollUrl: 'https://enroll.terminal.example.com/enroll',
+        recoverUrl: 'https://elsewhere.example.com/renew',
+      }),
+    ).toBe('https://elsewhere.example.com/renew')
+  })
+
+  it('is null when the enroll host carries no `enroll.` label (nothing to derive)', () => {
+    expect(recoveryRenewalUrlFor(CFG)).toBeNull()
+  })
+
+  it('posts to the NORMAL endpoint while the leaf is still valid', async () => {
+    const { dir, ks } = enrolledKs()
+    const timer = new FakeTimer()
+    const urls: string[] = []
+    const rotator = createCertRotator(
+      { ...CFG, enrollUrl: 'https://enroll.terminal.example.com/enroll' },
+      ks.loadIdentity()!,
+      ks,
+      {
+        timer,
+        renewBeforeMs: 1000,
+        fetchImpl: (async (u: string) => {
+          urls.push(u)
+          return jsonRes(200, { cert: 'NEWCERT', caChain: ['NEWCA'] })
+        }) as unknown as typeof fetch,
+        now: () => new Date(0),
+        parseCert: () => new Date(2000), // still valid at now=0
+      },
+    )
+    rotator.start()
+    timer.advance(1000)
+    await flush()
+    expect(urls).toEqual(['https://enroll.terminal.example.com/renew'])
+    rotator.stop()
+    rmSync(dir, { recursive: true, force: true })
+  })
+
+  it('posts to the RECOVERY endpoint once the leaf has already expired', async () => {
+    const { dir, ks } = enrolledKs()
+    const timer = new FakeTimer()
+    const urls: string[] = []
+    const rotator = createCertRotator(
+      { ...CFG, enrollUrl: 'https://enroll.terminal.example.com/enroll' },
+      ks.loadIdentity()!,
+      ks,
+      {
+        timer,
+        renewBeforeMs: 1000,
+        fetchImpl: (async (u: string) => {
+          urls.push(u)
+          return jsonRes(200, { cert: 'NEWCERT', caChain: ['NEWCA'] })
+        }) as unknown as typeof fetch,
+        now: () => new Date(10_000),
+        parseCert: () => new Date(2000), // expired 8s ago ⇒ delay clamps to 0
+      },
+    )
+    rotator.start()
+    timer.advance(0)
+    await flush()
+    expect(urls).toEqual(['https://recover.terminal.example.com/renew'])
+    rotator.stop()
+    rmSync(dir, { recursive: true, force: true })
+  })
+
+  it('fires onExhausted and STOPS retrying when the grace window is spent', async () => {
+    const { dir, ks } = enrolledKs()
+    const timer = new FakeTimer()
+    let attempts = 0
+    const rotator = createCertRotator(CFG, ks.loadIdentity()!, ks, {
+      timer,
+      renewBeforeMs: 1000,
+      retryBackoff: createBackoff({ baseMs: 500, jitter: false }),
+      fetchImpl: (async () => {
+        attempts += 1
+        throw new CertExpiredBeyondGraceError(40 * 86_400_000, 30 * 86_400_000)
+      }) as unknown as typeof fetch,
+      now: () => new Date(0),
+      parseCert: () => new Date(2000),
+    })
+    const errors: unknown[] = []
+    let exhausted: CertExpiredBeyondGraceError | null = null
+    rotator.onError((e) => errors.push(e))
+    rotator.onExhausted((e) => {
+      exhausted = e
+    })
+    rotator.start()
+    timer.advance(1000)
+    await flush()
+
+    expect(attempts).toBe(1)
+    expect(exhausted).toBeInstanceOf(CertExpiredBeyondGraceError)
+    // Terminal: no retry is armed, because only a re-pair can help — retrying forever is the log
+    // spam that buried the real signal in production (6380 identical warnings).
+    expect(errors).toHaveLength(0)
+    timer.advance(60_000)
+    await flush()
+    expect(attempts).toBe(1)
+    rmSync(dir, { recursive: true, force: true })
+  })
+})