diff --git a/apps/desktop/main.cjs b/apps/desktop/main.cjs
index 62edfc8..f8cb9c0 100644
--- a/apps/desktop/main.cjs
+++ b/apps/desktop/main.cjs
@@ -39,6 +39,9 @@ let activeHotkeyBinding = null;
 let updateCheckPromise = null;
 let updateReadyToInstall = false;
 let updateInstallRequested = false;
+let workerAuthPollTimer = null;
+let workerAuthPollInFlight = false;
+let usageCreditRefreshTimers = [];
 let desktopAuth = {
   token: "",
   account: null,
@@ -52,6 +55,9 @@ const MAX_DICTIONARY_ENTRIES = 1000;
 const MAX_DICTIONARY_SEND_ENTRIES = 200;
 const MAX_DICTIONARY_PHRASE_LENGTH = 60;
 const MAX_DICTIONARY_REPLACEMENT_LENGTH = 120;
+const WORKER_AUTH_POLL_INTERVAL_MS = 5 * 60 * 1000;
+const POST_TRANSCRIPTION_USAGE_REFRESH_DELAYS_MS = [5_000, 20_000, 60_000];
+const DEFERRED_USAGE_REFRESH_RETRY_MS = 5_000;
 
 const hotkeyState = {
   ctrlDown: false,
@@ -131,6 +137,7 @@ if (!singleInstanceLock) {
     createTray();
     registerNativeHotkey();
     configureAutoUpdates();
+    configureWorkerAuthPolling();
     void refreshWorkerAuth();
   });
 }
@@ -161,6 +168,11 @@ app.on("will-quit", () => {
   }
   logSink?.close();
   logSink = null;
+  clearUsageCreditRefreshTimers();
+  if (workerAuthPollTimer) {
+    clearInterval(workerAuthPollTimer);
+    workerAuthPollTimer = null;
+  }
 });
 
 function createWindow() {
@@ -569,15 +581,86 @@ function registerIpc() {
       }
       exitDictationWindowMode();
       patchStatus({ state: "idle", message: "Ready", lastTranscript: result });
+      scheduleUsageCreditRefresh("transcription-complete");
     } else {
       logWarn("transcription:submit:empty-text", summarizeTranscriptionResult(result));
       exitDictationWindowMode();
       patchStatus({ state: "idle", message: "No speech detected" });
+      scheduleUsageCreditRefresh("transcription-empty");
     }
     return result;
   });
 }
 
+function configureWorkerAuthPolling() {
+  if (workerAuthPollTimer) {
+    return;
+  }
+
+  workerAuthPollTimer = setInterval(() => {
+    void refreshWorkerAuthFromPoll("interval");
+  }, WORKER_AUTH_POLL_INTERVAL_MS);
+  workerAuthPollTimer.unref?.();
+}
+
+async function refreshWorkerAuthFromPoll(reason) {
+  if (!desktopAuth.token || workerAuthPollInFlight) {
+    return;
+  }
+
+  if (isDictationBusy()) {
+    return;
+  }
+
+  workerAuthPollInFlight = true;
+  try {
+    logInfo("worker:auth-poll:start", { reason });
+    await refreshWorkerAuth();
+  } catch (error) {
+    logWarn("worker:auth-poll:failed", { reason, error: formatErrorForLog(error) });
+  } finally {
+    workerAuthPollInFlight = false;
+  }
+}
+
+function scheduleUsageCreditRefresh(reason) {
+  clearUsageCreditRefreshTimers();
+
+  for (const delayMs of POST_TRANSCRIPTION_USAGE_REFRESH_DELAYS_MS) {
+    scheduleUsageCreditRefreshAttempt(reason, delayMs);
+  }
+}
+
+function clearUsageCreditRefreshTimers() {
+  for (const timer of usageCreditRefreshTimers) {
+    clearTimeout(timer);
+  }
+  usageCreditRefreshTimers = [];
+}
+
+function scheduleUsageCreditRefreshAttempt(reason, delayMs) {
+  const timer = setTimeout(() => {
+    usageCreditRefreshTimers = usageCreditRefreshTimers.filter((candidate) => candidate !== timer);
+
+    if (!desktopAuth.token) {
+      return;
+    }
+
+    if (workerAuthPollInFlight || isDictationBusy()) {
+      scheduleUsageCreditRefreshAttempt(reason, DEFERRED_USAGE_REFRESH_RETRY_MS);
+      return;
+    }
+
+    void refreshWorkerAuthFromPoll(reason);
+  }, delayMs);
+  timer.unref?.();
+  usageCreditRefreshTimers.push(timer);
+}
+
+function isDictationBusy() {
+  return status.state === "recording" || status.state === "transcribing" || status.state === "pasting";
+}
+
 function configureAutoUpdates() {
   if (!app.isPackaged) {
     logInfo("updates:skip-unpackaged");
@@ -848,6 +931,7 @@ async function startDeviceLogin() {
   }
 
   desktopAuth = { token: "", account: null, billing: null };
+  clearUsageCreditRefreshTimers();
   authGeneration += 1;
   saveDesktopAuth();
   patchStatus({
@@ -917,6 +1001,7 @@ async function pollDeviceLogin(deviceCode, deviceName) {
 
 async function logoutDevice() {
   desktopAuth = { token: "", account: null, billing: null };
+  clearUsageCreditRefreshTimers();
   authGeneration += 1;
   saveDesktopAuth();
   patchStatus({
diff --git a/apps/worker/src/index.ts b/apps/worker/src/index.ts
index cb92b71..79c5810 100644
--- a/apps/worker/src/index.ts
+++ b/apps/worker/src/index.ts
@@ -203,6 +203,7 @@ const CLEANUP_USER_PROMPT_SUFFIX = `
 </transcript>`;
 
 const app = new Hono<{ Bindings: Env }>();
+const DESKTOP_AUTH_LIVE_BILLING_TIMEOUT_MS = 1_500;
 
 app.use(
   "/health/*",
@@ -286,7 +287,7 @@ app.get("/health", (c) =>
 );
 
 app.get("/health/auth", async (c) => {
-  const authorized = await authorizeDesktop(c.req.raw, c.env);
+  const authorized = await authorizeDesktop(c.req.raw, c.env, { liveBilling: true });
   if (!authorized) {
     return c.json<TranscriptionError>({ error: "Unauthorized" }, 401);
   }
@@ -947,7 +948,11 @@ function isAuthSession(value: unknown): value is AuthSession {
   return isRecord(value) && isRecord(value.user) && typeof value.user.id === "string" && typeof value.user.email === "string" && typeof value.user.name === "string";
 }
 
-async function authorizeDesktop(request: Request, env: Env): Promise<DesktopAuthorization | null> {
+async function authorizeDesktop(
+  request: Request,
+  env: Env,
+  options: { liveBilling?: boolean } = {}
+): Promise<DesktopAuthorization | null> {
   const authorization = request.headers.get("authorization") ?? "";
   const token = authorization.startsWith("Bearer ") ? authorization.slice("Bearer ".length).trim() : "";
   if (!token) {
@@ -967,7 +972,9 @@ async function authorizeDesktop(request: Request, env: Env): Promise<DesktopAuth
     return null;
   }
 
-  const billing = await getCachedBilling(env, device.user_id);
+  const billing = options.liveBilling
+    ? await getDesktopAuthLiveBilling(env, device.user_id)
+    : await getCachedBilling(env, device.user_id);
 
   return {
     deviceId: device.id,
@@ -977,6 +984,27 @@ async function authorizeDesktop(request: Request, env: Env): Promise<DesktopAuth
   };
 }
 
+async function getDesktopAuthLiveBilling(env: Env, userId: string): Promise<AccountBillingStatus> {
+  try {
+    return await withTimeout(
+      getBilling(env, userId),
+      DESKTOP_AUTH_LIVE_BILLING_TIMEOUT_MS,
+      `desktop auth billing timed out after ${DESKTOP_AUTH_LIVE_BILLING_TIMEOUT_MS}ms`
+    );
+  } catch (error) {
+    console.warn(
+      JSON.stringify({
+        level: "warn",
+        event: "desktop-auth:live-billing-fallback",
+        userId,
+        timeoutMs: DESKTOP_AUTH_LIVE_BILLING_TIMEOUT_MS,
+        error: formatError(error)
+      })
+    );
+    return getCachedBilling(env, userId);
+  }
+}
+
 async function getBilling(env: Env, userId: string): Promise<AccountBillingStatus> {
   const billing = await ensureBillingProfile(env, userId);
   if (!isPolarConfigured(env)) {