Phase5: Automate bill creation

src/app/[locale]/admin/cron/page.tsx

@@ -0,0 +1,44 @@
+import { redirect } from "next/navigation";
+import { getTranslations } from "next-intl/server";
+import { getSessionUser } from "@/lib/session";
+import {
+  getLastSuccessfulCronRuns,
+  listRecentCronRuns,
+} from "@/lib/db";
+import { CronControls } from "@/components/admin/cron/cron-controls";
+
+/**
+ * /admin/cron — automation dashboard.
+ *
+ * Shows:
+ *   - Last successful run of each kind, with relative time
+ *   - Two "Run now" buttons (admin-triggered manual sweeps)
+ *   - Recent runs table (last 30)
+ *
+ * Platform-admin gated server-side.
+ */
+export default async function AdminCronPage() {
+  const user = await getSessionUser();
+  if (!user || !user.isPlatform) redirect("/login");
+  const t = await getTranslations("adminCron");
+
+  const [recent, lastSuccess] = await Promise.all([
+    listRecentCronRuns(30),
+    getLastSuccessfulCronRuns(),
+  ]);
+
+  return (
+    <main className="max-w-5xl mx-auto px-6 py-8">
+      <div className="mb-8 animate-in">
+        <h1 className="font-display text-2xl font-semibold accent-rule">
+          {t("title")}
+        </h1>
+        <p className="text-sm text-text-secondary mt-3">{t("subtitle")}</p>
+      </div>
+      <CronControls
+        initialRecent={recent}
+        initialLastSuccess={lastSuccess}
+      />
+    </main>
+  );
+}

src/app/[locale]/admin/page.tsx

@@ -61,6 +61,12 @@ export default async function AdminPage() {
           >
             {t("billingTool")}
           </a>
+          <a
+            href="/admin/cron"
+            className="text-sm px-4 py-2 rounded-lg border border-border text-text-secondary hover:text-text-primary hover:border-text-secondary transition-colors"
+          >
+            {t("cronTool")}
+          </a>
           <a
             href="/admin/openclaw"
             className="text-sm px-4 py-2 rounded-lg border border-border text-text-secondary hover:text-text-primary hover:border-text-secondary transition-colors"

src/app/api/admin/cron/issue-monthly/route.ts

@@ -0,0 +1,68 @@
+import { NextResponse } from "next/server";
+import { z } from "zod";
+import { getSessionUser, requirePlatformRole } from "@/lib/session";
+import { runMonthlyIssuance } from "@/lib/cron";
+import { safeError } from "@/lib/errors";
+
+/**
+ * POST /api/admin/cron/issue-monthly
+ *
+ * Admin-side manual trigger for the issuance sweep — same business
+ * logic as /api/cron/issue-monthly, different auth (session-based
+ * platform role check) and the option to override the target
+ * year/month from the request body.
+ *
+ * Body (all optional):
+ *   { year?: number, month?: number }
+ *
+ * Default target is the previous local month — matching what the
+ * automated cron would do. Override is useful for catching up after
+ * a failed run or re-billing a past month after fixing data.
+ */
+const bodySchema = z.object({
+  year: z.number().int().min(2000).max(3000).optional(),
+  month: z.number().int().min(1).max(12).optional(),
+});
+
+export async function POST(request: Request) {
+  let user;
+  try {
+    await requirePlatformRole();
+    user = await getSessionUser();
+  } catch {
+    return NextResponse.json({ error: "Forbidden" }, { status: 403 });
+  }
+  if (!user) {
+    return NextResponse.json({ error: "Unauthorized" }, { status: 401 });
+  }
+  const body = await request.json().catch(() => ({}));
+  const parsed = bodySchema.safeParse(body);
+  if (!parsed.success) {
+    return NextResponse.json(
+      { error: "Invalid request", details: parsed.error.flatten() },
+      { status: 400 }
+    );
+  }
+  if (
+    (parsed.data.year && !parsed.data.month) ||
+    (parsed.data.month && !parsed.data.year)
+  ) {
+    return NextResponse.json(
+      { error: "year and month must both be provided, or neither" },
+      { status: 400 }
+    );
+  }
+  try {
+    const { runId, summary } = await runMonthlyIssuance({
+      triggeredBy: user.id,
+      year: parsed.data.year,
+      month: parsed.data.month,
+    });
+    return NextResponse.json({ runId, ...summary });
+  } catch (e) {
+    return NextResponse.json(
+      { error: safeError(e, "Issuance sweep failed.") },
+      { status: 500 }
+    );
+  }
+}

src/app/api/admin/cron/runs/route.ts

@@ -0,0 +1,27 @@
+import { NextResponse } from "next/server";
+import { requirePlatformRole } from "@/lib/session";
+import {
+  getLastSuccessfulCronRuns,
+  listRecentCronRuns,
+} from "@/lib/db";
+
+/**
+ * GET /api/admin/cron/runs
+ *
+ * Returns recent cron run history plus per-kind "last successful"
+ * summary for the admin /admin/cron dashboard.
+ *
+ * Response: { recent: CronRun[]; lastSuccess: { monthlyIssue, reminders } }
+ */
+export async function GET() {
+  try {
+    await requirePlatformRole();
+  } catch {
+    return NextResponse.json({ error: "Forbidden" }, { status: 403 });
+  }
+  const [recent, lastSuccess] = await Promise.all([
+    listRecentCronRuns(30),
+    getLastSuccessfulCronRuns(),
+  ]);
+  return NextResponse.json({ recent, lastSuccess });
+}

src/app/api/admin/cron/send-reminders/route.ts

@@ -0,0 +1,34 @@
+import { NextResponse } from "next/server";
+import { getSessionUser, requirePlatformRole } from "@/lib/session";
+import { runReminderSweep } from "@/lib/cron";
+import { safeError } from "@/lib/errors";
+
+/**
+ * POST /api/admin/cron/send-reminders
+ *
+ * Admin-side manual trigger for the reminder sweep. Same logic
+ * as the machine path; session-based platform-role auth.
+ */
+export async function POST() {
+  let user;
+  try {
+    await requirePlatformRole();
+    user = await getSessionUser();
+  } catch {
+    return NextResponse.json({ error: "Forbidden" }, { status: 403 });
+  }
+  if (!user) {
+    return NextResponse.json({ error: "Unauthorized" }, { status: 401 });
+  }
+  try {
+    const { runId, summary } = await runReminderSweep({
+      triggeredBy: user.id,
+    });
+    return NextResponse.json({ runId, ...summary });
+  } catch (e) {
+    return NextResponse.json(
+      { error: safeError(e, "Reminder sweep failed.") },
+      { status: 500 }
+    );
+  }
+}

src/app/api/cron/issue-monthly/route.ts

@@ -0,0 +1,42 @@
+import { NextResponse } from "next/server";
+import { runMonthlyIssuance, verifyCronBearer } from "@/lib/cron";
+import { safeError } from "@/lib/errors";
+
+/**
+ * POST /api/cron/issue-monthly
+ *
+ * Machine entry point for the monthly issuance sweep. Authentication
+ * is the shared bearer token in CRON_BEARER_TOKEN, injected from
+ * OpenBao via the portal-cron K8s Secret. The K8s CronJob sends:
+ *
+ *   curl -X POST -H "Authorization: Bearer $CRON_BEARER_TOKEN" \
+ *        https://app.pieced.ch/api/cron/issue-monthly
+ *
+ * The sweep targets the calendar month that ended just before
+ * "now" in Europe/Zurich. Running it on June 1st at 00:30 Swiss
+ * time bills May; running it on July 5th bills June; etc. The
+ * uniqueness constraint on (org, period_start) makes re-runs
+ * harmless — already-issued orgs are counted as skipped.
+ *
+ * Returns the summary {success, failure, skipped} JSON. The
+ * CronJob doesn't look at the response body (just the status
+ * code) but having a useful one helps debugging via curl.
+ */
+export const dynamic = "force-dynamic";
+
+export async function POST(request: Request) {
+  if (!verifyCronBearer(request.headers.get("authorization"))) {
+    return NextResponse.json({ error: "Unauthorized" }, { status: 401 });
+  }
+  try {
+    const { runId, summary } = await runMonthlyIssuance({
+      triggeredBy: "cron",
+    });
+    return NextResponse.json({ runId, ...summary });
+  } catch (e) {
+    return NextResponse.json(
+      { error: safeError(e, "Issuance sweep failed.") },
+      { status: 500 }
+    );
+  }
+}

src/app/api/cron/send-reminders/route.ts

@@ -0,0 +1,33 @@
+import { NextResponse } from "next/server";
+import { runReminderSweep, verifyCronBearer } from "@/lib/cron";
+import { safeError } from "@/lib/errors";
+
+/**
+ * POST /api/cron/send-reminders
+ *
+ * Machine entry point for the daily reminder sweep. Same auth
+ * (bearer token in CRON_BEARER_TOKEN) and the same response
+ * contract as /api/cron/issue-monthly.
+ *
+ * Schedule: 09:00 Europe/Zurich daily. Picks invoices that are
+ * past their due date and haven't received the corresponding
+ * reminder level yet; sends one email per invoice per run.
+ */
+export const dynamic = "force-dynamic";
+
+export async function POST(request: Request) {
+  if (!verifyCronBearer(request.headers.get("authorization"))) {
+    return NextResponse.json({ error: "Unauthorized" }, { status: 401 });
+  }
+  try {
+    const { runId, summary } = await runReminderSweep({
+      triggeredBy: "cron",
+    });
+    return NextResponse.json({ runId, ...summary });
+  } catch (e) {
+    return NextResponse.json(
+      { error: safeError(e, "Reminder sweep failed.") },
+      { status: 500 }
+    );
+  }
+}

src/components/admin/cron/cron-controls.tsx

@@ -0,0 +1,229 @@
+"use client";
+
+import { useState } from "react";
+import { useTranslations, useFormatter } from "next-intl";
+import { Card } from "@/components/ui/card";
+import type { CronRun } from "@/types";
+
+interface Props {
+  initialRecent: CronRun[];
+  initialLastSuccess: {
+    monthlyIssue: CronRun | null;
+    reminders: CronRun | null;
+  };
+}
+
+/**
+ * Admin cron dashboard. Server pre-loads `initialRecent` and
+ * `initialLastSuccess`; "Run now" clicks POST to the admin
+ * endpoints, then re-fetch the history via GET /api/admin/cron/runs.
+ *
+ * The trigger buttons disable while busy and surface the resulting
+ * counters inline so the admin gets immediate feedback without
+ * needing to scroll to the history table.
+ */
+export function CronControls({ initialRecent, initialLastSuccess }: Props) {
+  const t = useTranslations("adminCron");
+  const fmt = useFormatter();
+  const [recent, setRecent] = useState(initialRecent);
+  const [lastSuccess, setLastSuccess] = useState(initialLastSuccess);
+  const [busy, setBusy] = useState<null | "issue" | "reminders">(null);
+  const [flash, setFlash] = useState<null | {
+    kind: "issue" | "reminders";
+    ok: boolean;
+    summary: string;
+  }>(null);
+
+  const refresh = async () => {
+    try {
+      const res = await fetch("/api/admin/cron/runs");
+      if (!res.ok) return;
+      const data = await res.json();
+      setRecent(data.recent);
+      setLastSuccess(data.lastSuccess);
+    } catch {
+      // swallow — refresh is opportunistic
+    }
+  };
+
+  const triggerIssue = async () => {
+    setBusy("issue");
+    setFlash(null);
+    try {
+      const res = await fetch("/api/admin/cron/issue-monthly", {
+        method: "POST",
+      });
+      const j = await res.json();
+      if (!res.ok) {
+        setFlash({
+          kind: "issue",
+          ok: false,
+          summary: j.error ?? `HTTP ${res.status}`,
+        });
+      } else {
+        setFlash({
+          kind: "issue",
+          ok: true,
+          summary: t("flashIssueOk", {
+            success: j.successCount,
+            skipped: j.skippedCount,
+            failure: j.failureCount,
+          }),
+        });
+      }
+      await refresh();
+    } finally {
+      setBusy(null);
+    }
+  };
+
+  const triggerReminders = async () => {
+    setBusy("reminders");
+    setFlash(null);
+    try {
+      const res = await fetch("/api/admin/cron/send-reminders", {
+        method: "POST",
+      });
+      const j = await res.json();
+      if (!res.ok) {
+        setFlash({
+          kind: "reminders",
+          ok: false,
+          summary: j.error ?? `HTTP ${res.status}`,
+        });
+      } else {
+        setFlash({
+          kind: "reminders",
+          ok: true,
+          summary: t("flashRemindersOk", {
+            success: j.successCount,
+            skipped: j.skippedCount,
+            failure: j.failureCount,
+          }),
+        });
+      }
+      await refresh();
+    } finally {
+      setBusy(null);
+    }
+  };
+
+  const fmtRelative = (iso: string | null) => {
+    if (!iso) return t("never");
+    return fmt.dateTime(new Date(iso), {
+      dateStyle: "medium",
+      timeStyle: "short",
+    });
+  };
+
+  return (
+    <div className="space-y-8">
+      <section className="grid gap-4 md:grid-cols-2">
+        <Card>
+          <h2 className="text-xs uppercase tracking-wider text-text-muted mb-2">
+            {t("monthlyIssue")}
+          </h2>
+          <p className="text-xs text-text-secondary mb-1">
+            {t("scheduleIssueLabel")}: <span className="font-mono">{t("scheduleIssueValue")}</span>
+          </p>
+          <p className="text-xs text-text-secondary mb-3">
+            {t("lastSuccess")}: <span className="font-mono">{fmtRelative(lastSuccess.monthlyIssue?.startedAt ?? null)}</span>
+          </p>
+          <button
+            onClick={triggerIssue}
+            disabled={busy !== null}
+            className="px-4 py-2 rounded-md bg-accent text-white text-sm font-medium hover:bg-accent-dim transition-colors disabled:opacity-50 cursor-pointer"
+          >
+            {busy === "issue" ? t("running") : t("runIssueNow")}
+          </button>
+        </Card>
+        <Card>
+          <h2 className="text-xs uppercase tracking-wider text-text-muted mb-2">
+            {t("reminders")}
+          </h2>
+          <p className="text-xs text-text-secondary mb-1">
+            {t("scheduleReminderLabel")}: <span className="font-mono">{t("scheduleReminderValue")}</span>
+          </p>
+          <p className="text-xs text-text-secondary mb-3">
+            {t("lastSuccess")}: <span className="font-mono">{fmtRelative(lastSuccess.reminders?.startedAt ?? null)}</span>
+          </p>
+          <button
+            onClick={triggerReminders}
+            disabled={busy !== null}
+            className="px-4 py-2 rounded-md bg-accent text-white text-sm font-medium hover:bg-accent-dim transition-colors disabled:opacity-50 cursor-pointer"
+          >
+            {busy === "reminders" ? t("running") : t("runRemindersNow")}
+          </button>
+        </Card>
+      </section>
+
+      {flash && (
+        <div
+          className={`p-3 rounded-md border text-sm ${
+            flash.ok
+              ? "border-success bg-success/10 text-success"
+              : "border-error bg-error/10 text-error"
+          }`}
+        >
+          {flash.summary}
+        </div>
+      )}
+
+      <section>
+        <h2 className="text-xs uppercase tracking-wider text-text-muted mb-3">
+          {t("recentRuns")}
+        </h2>
+        <Card>
+          {recent.length === 0 ? (
+            <p className="text-sm text-text-muted italic py-4">
+              {t("noRunsYet")}
+            </p>
+          ) : (
+            <table className="w-full text-sm">
+              <thead className="text-xs text-text-muted text-left">
+                <tr>
+                  <th className="pb-2">{t("startedCol")}</th>
+                  <th className="pb-2">{t("kindCol")}</th>
+                  <th className="pb-2">{t("triggeredByCol")}</th>
+                  <th className="pb-2 text-right">{t("okCol")}</th>
+                  <th className="pb-2 text-right">{t("skipCol")}</th>
+                  <th className="pb-2 text-right">{t("failCol")}</th>
+                </tr>
+              </thead>
+              <tbody>
+                {recent.map((r) => (
+                  <tr key={r.id} className="border-t border-border align-top">
+                    <td className="py-2 text-xs font-mono">
+                      {fmtRelative(r.startedAt)}
+                    </td>
+                    <td className="py-2 text-xs">
+                      {t(`kind.${r.runKind}` as any)}
+                    </td>
+                    <td className="py-2 text-xs text-text-secondary font-mono">
+                      {r.triggeredBy === "cron"
+                        ? t("triggeredByCron")
+                        : r.triggeredBy.slice(0, 8) + "…"}
+                    </td>
+                    <td className="py-2 text-right font-mono text-xs text-success">
+                      {r.successCount}
+                    </td>
+                    <td className="py-2 text-right font-mono text-xs text-text-secondary">
+                      {r.skippedCount}
+                    </td>
+                    <td
+                      className={`py-2 text-right font-mono text-xs ${
+                        r.failureCount > 0 ? "text-error" : "text-text-muted"
+                      }`}
+                    >
+                      {r.failureCount}
+                    </td>
+                  </tr>
+                ))}
+              </tbody>
+            </table>
+          )}
+        </Card>
+      </section>
+    </div>
+  );
+}

src/lib/cron.ts

@@ -0,0 +1,360 @@
+/**
+ * Phase 5 — Automated billing cron logic.
+ *
+ * This module hosts the two sweeps:
+ *   - runMonthlyIssuance() — invoked monthly to generate invoices
+ *     for orgs opted into auto-issuance. Idempotent via the
+ *     uniq_invoices_org_period constraint on invoices: a re-run
+ *     for an org that's already been billed for the target period
+ *     gets caught as a duplicate and counted as a skip, not a
+ *     failure.
+ *   - runReminderSweep() — invoked daily. Walks open/overdue
+ *     invoices, sends the appropriate reminder level (1/2/3) once
+ *     per invoice via the invoice_reminders unique-key constraint.
+ *
+ * Both entry points return a summary {success, failure, skipped}
+ * that the caller persists via finishCronRun(). The shared
+ * structure means the HTTP routes (machine + admin variants) are
+ * trivial wrappers.
+ *
+ * Time-of-month math is timezone-aware: we read the calendar in
+ * Europe/Zurich rather than UTC, because the K8s CronJob schedules
+ * at 00:30 local time on the 1st — UTC at that moment is still in
+ * the previous month, and a naive `getUTCMonth() - 1` would bill
+ * the wrong period.
+ */
+
+import {
+  finishCronRun,
+  getLastSuccessfulCronRuns,
+  getOrgBilling,
+  getReminderLevelsSent,
+  listAutoIssueOrgIds,
+  listInvoicesPendingReminders,
+  recordReminderSent,
+  startCronRun,
+  syncOverdueInvoices,
+} from "./db";
+import { generateInvoice } from "./billing";
+import { sendInvoiceReminderEmail } from "./email";
+
+// The org_billing snapshot's company_name field doubles as the
+// recipient name when no separate "billing contact" exists in
+// our schema. Same convention as Phase 3's issuance email.
+
+// All cron timing assumes Switzerland's calendar — the operator,
+// the customers, and the legal basis (Swiss MWST) are all here.
+const TZ = "Europe/Zurich";
+
+export type CronSummary = {
+  successCount: number;
+  failureCount: number;
+  skippedCount: number;
+  errorDetails: Array<{
+    orgId?: string;
+    invoiceId?: string;
+    reason: string;
+  }>;
+};
+
+// ---------------------------------------------------------------------------
+// Monthly issuance
+// ---------------------------------------------------------------------------
+
+/**
+ * The (year, month) of the calendar month that ended JUST BEFORE
+ * `now` in the configured timezone. This is what the issuance
+ * sweep bills.
+ *
+ * Reading the local-time calendar avoids a UTC-vs-local off-by-one
+ * when the sweep runs at 00:30 Zurich and UTC is still in the
+ * previous month.
+ */
+export function previousLocalMonth(
+  now: Date = new Date()
+): { year: number; month: number } {
+  const fmt = new Intl.DateTimeFormat("en-CA", {
+    timeZone: TZ,
+    year: "numeric",
+    month: "2-digit",
+  });
+  const parts = fmt.formatToParts(now);
+  const year = Number(parts.find((p) => p.type === "year")!.value);
+  const month = Number(parts.find((p) => p.type === "month")!.value);
+  if (month === 1) return { year: year - 1, month: 12 };
+  return { year, month: month - 1 };
+}
+
+export async function runMonthlyIssuance(opts: {
+  triggeredBy: string;
+  /** Override target year/month — defaults to previous local month. */
+  year?: number;
+  month?: number;
+}): Promise<{ runId: string; summary: CronSummary }> {
+  const target =
+    opts.year && opts.month
+      ? { year: opts.year, month: opts.month }
+      : previousLocalMonth();
+  const runId = await startCronRun("monthly_issue", opts.triggeredBy);
+  const summary: CronSummary = {
+    successCount: 0,
+    failureCount: 0,
+    skippedCount: 0,
+    errorDetails: [],
+  };
+
+  try {
+    const orgIds = await listAutoIssueOrgIds();
+    for (const orgId of orgIds) {
+      try {
+        const orgBilling = await getOrgBilling(orgId);
+        if (!orgBilling) {
+          // Auto-issue is enabled but billing details are missing.
+          // Skip rather than fail — the admin needs to complete the
+          // address before invoicing can succeed.
+          summary.skippedCount += 1;
+          summary.errorDetails.push({
+            orgId,
+            reason: "org_billing not configured",
+          });
+          continue;
+        }
+        // Derive invoice locale from the org's country. PieCed is
+        // Swiss-default; CH/LI/AT/DE customers get the German PDF,
+        // FR/BE/LU customers get French, IT customers get Italian,
+        // anything else falls through to English. Customers needing
+        // a different locale can still trigger a manual issuance
+        // with an explicit override from the admin UI.
+        const locale = pickLocaleForCountry(orgBilling.country);
+        const { invoice } = await generateInvoice({
+          zitadelOrgId: orgId,
+          year: target.year,
+          month: target.month,
+          locale,
+        });
+        if (invoice) {
+          summary.successCount += 1;
+        } else {
+          // dryRun path — shouldn't happen in production. Defensive.
+          summary.skippedCount += 1;
+        }
+      } catch (e: any) {
+        // The uniqueness constraint on (zitadel_org_id, period_start)
+        // surfaces as "An invoice already exists for this org and
+        // billing period" from createInvoice. Re-running the cron
+        // mid-month or after a partial completion is therefore safe:
+        // already-billed orgs end up as skipped, not failed.
+        const msg = String(e?.message ?? e);
+        const isAlreadyIssued = /already exists for this org and billing period/i.test(
+          msg
+        );
+        if (isAlreadyIssued) {
+          summary.skippedCount += 1;
+        } else {
+          summary.failureCount += 1;
+          summary.errorDetails.push({ orgId, reason: msg });
+          console.error(
+            `runMonthlyIssuance: org ${orgId} failed:`,
+            e
+          );
+        }
+      }
+    }
+    await finishCronRun(runId, summary);
+    return { runId, summary };
+  } catch (e) {
+    // Catastrophic — the sweep itself failed (DB down, etc).
+    summary.failureCount += 1;
+    summary.errorDetails.push({
+      reason: `sweep aborted: ${e instanceof Error ? e.message : String(e)}`,
+    });
+    await finishCronRun(runId, summary).catch(() => undefined);
+    throw e;
+  }
+}
+
+// ---------------------------------------------------------------------------
+// Reminder sweep
+// ---------------------------------------------------------------------------
+
+/**
+ * Which reminder level (if any) is due now for this invoice?
+ *
+ * Logic:
+ *   - days_past_due >= 30 AND level 3 not yet sent → 3 (final)
+ *   - else days_past_due >= 14 AND level 2 not yet sent → 2
+ *   - else days_past_due >=  7 AND level 1 not yet sent → 1
+ *   - else → null (nothing to do this run)
+ *
+ * One reminder per cron run per invoice — highest applicable
+ * un-sent level wins. If a customer fell behind quickly and is
+ * already 35 days past due without ever having received levels
+ * 1 or 2 (e.g. the cron was broken for a while), they get level
+ * 3 directly. We don't backfill lower levels.
+ */
+function nextReminderLevel(
+  daysPastDue: number,
+  sent: Set<number>
+): 1 | 2 | 3 | null {
+  if (daysPastDue >= 30 && !sent.has(3)) return 3;
+  if (daysPastDue >= 14 && !sent.has(2)) return 2;
+  if (daysPastDue >= 7 && !sent.has(1)) return 1;
+  return null;
+}
+
+function daysBetween(later: Date, earlier: Date): number {
+  const ms = later.getTime() - earlier.getTime();
+  return Math.floor(ms / (1000 * 60 * 60 * 24));
+}
+
+/**
+ * Pick a default invoice locale based on the org's country
+ * (ISO 3166-1 alpha-2 code from org_billing.country). PieCed is
+ * primarily a Swiss-German operator; CH/LI/AT/DE get German,
+ * FR/BE/LU get French, IT gets Italian, anything else falls
+ * through to English.
+ *
+ * This only drives the automated issuance default. Manual
+ * issuance from the admin UI takes an explicit override.
+ */
+function pickLocaleForCountry(country: string): "de" | "en" | "fr" | "it" {
+  const c = country.toUpperCase();
+  if (["CH", "LI", "AT", "DE"].includes(c)) return "de";
+  if (["FR", "BE", "LU"].includes(c)) return "fr";
+  if (c === "IT") return "it";
+  return "en";
+}
+
+export async function runReminderSweep(opts: {
+  triggeredBy: string;
+}): Promise<{ runId: string; summary: CronSummary }> {
+  const runId = await startCronRun("reminders", opts.triggeredBy);
+  const summary: CronSummary = {
+    successCount: 0,
+    failureCount: 0,
+    skippedCount: 0,
+    errorDetails: [],
+  };
+
+  try {
+    // Flip stale 'open' → 'overdue' first so the listing reflects
+    // current status, and audit trails stay accurate.
+    await syncOverdueInvoices().catch((e) => {
+      console.warn("syncOverdueInvoices failed during reminder sweep:", e);
+    });
+
+    const candidates = await listInvoicesPendingReminders();
+    const now = new Date();
+
+    for (const inv of candidates) {
+      try {
+        const sent = await getReminderLevelsSent(inv.id);
+        const dueAt = new Date(inv.dueAt);
+        const days = daysBetween(now, dueAt);
+        const level = nextReminderLevel(days, sent);
+        if (level === null) {
+          summary.skippedCount += 1;
+          continue;
+        }
+        const billing = inv.billingSnapshot;
+        if (!billing.billingEmail) {
+          summary.skippedCount += 1;
+          summary.errorDetails.push({
+            invoiceId: inv.id,
+            reason: "no billing email on snapshot",
+          });
+          continue;
+        }
+        const supportedLocales: Array<"de" | "en" | "fr" | "it"> = [
+          "de", "en", "fr", "it",
+        ];
+        const locale = supportedLocales.includes(inv.locale as any)
+          ? (inv.locale as "de" | "en" | "fr" | "it")
+          : "de";
+
+        await sendInvoiceReminderEmail({
+          to: billing.billingEmail,
+          contactName: billing.companyName,
+          companyName: billing.companyName,
+          invoiceNumber: inv.invoiceNumber,
+          totalChf: inv.totalChf,
+          currency: "CHF",
+          dueAt: inv.dueAt,
+          daysPastDue: days,
+          level,
+          locale,
+        });
+        // Record AFTER the send. If the SMTP send fails the email
+        // helper logs and doesn't throw, so we'd still record — but
+        // that's a tradeoff we accept: at-least-once delivery semantics
+        // with logged warnings is better than at-most-once where a
+        // transient failure stops the customer from ever getting
+        // reminded. If duplicate-reminder fatigue becomes a real
+        // problem in production, switch to: send first, only record
+        // on confirmed transporter success.
+        await recordReminderSent({
+          invoiceId: inv.id,
+          level,
+          sentBy: opts.triggeredBy,
+          emailSentTo: billing.billingEmail,
+        });
+        summary.successCount += 1;
+      } catch (e: any) {
+        summary.failureCount += 1;
+        summary.errorDetails.push({
+          invoiceId: inv.id,
+          reason: String(e?.message ?? e),
+        });
+        console.error(
+          `runReminderSweep: invoice ${inv.id} failed:`,
+          e
+        );
+      }
+    }
+    await finishCronRun(runId, summary);
+    return { runId, summary };
+  } catch (e) {
+    summary.failureCount += 1;
+    summary.errorDetails.push({
+      reason: `sweep aborted: ${e instanceof Error ? e.message : String(e)}`,
+    });
+    await finishCronRun(runId, summary).catch(() => undefined);
+    throw e;
+  }
+}
+
+// ---------------------------------------------------------------------------
+// Auth — bearer token for the machine endpoints
+// ---------------------------------------------------------------------------
+
+/**
+ * Constant-time bearer token check. The CRON_BEARER_TOKEN env var
+ * is injected from OpenBao via the portal-cron K8s Secret. Both
+ * the CronJob and the portal Deployment reference it; the
+ * CronJob sends it in the Authorization header, the portal checks
+ * with timing-safe equals to defeat character-by-character probing.
+ */
+export function verifyCronBearer(authHeader: string | null): boolean {
+  if (!authHeader) return false;
+  const expected = process.env.CRON_BEARER_TOKEN;
+  if (!expected || expected.length < 16) {
+    // Treat misconfiguration as a hard refusal so a missing/
+    // accidentally-empty token doesn't silently grant access.
+    return false;
+  }
+  if (!authHeader.startsWith("Bearer ")) return false;
+  const got = authHeader.slice("Bearer ".length).trim();
+  if (got.length !== expected.length) return false;
+  // Constant-time byte compare. Node's Buffer.compare and the
+  // crypto.timingSafeEqual function both work, but the latter
+  // throws on length mismatch; the length pre-check above
+  // protects against that.
+  let diff = 0;
+  for (let i = 0; i < got.length; i++) {
+    diff |= got.charCodeAt(i) ^ expected.charCodeAt(i);
+  }
+  return diff === 0;
+}
+
+// Re-export for the admin UI to render "last run X ago" indicators.
+export { getLastSuccessfulCronRuns };

src/lib/db.ts

@@ -598,6 +598,26 @@ const MIGRATION_SQL = `
   );
   CREATE INDEX IF NOT EXISTS idx_stripe_events_type_received
     ON stripe_events (event_type, received_at DESC);
+
+  -- Phase 5: Cron run history. One row per invocation of either the
+  -- monthly issuance sweep or the daily reminder sweep, regardless of
+  -- whether it ran from K8s CronJob or an admin's manual trigger.
+  -- The summary counters let the admin UI render "last run: 12 issued,
+  -- 0 failed" without joining against invoices/reminders. Detail rows
+  -- live in the JSONB error_details on failure for diagnosis.
+  CREATE TABLE IF NOT EXISTS cron_run_history (
+    id             UUID PRIMARY KEY DEFAULT gen_random_uuid(),
+    run_kind       TEXT NOT NULL CHECK (run_kind IN ('monthly_issue','reminders')),
+    triggered_by   TEXT NOT NULL,  -- 'cron' or '<admin-user-id>'
+    started_at     TIMESTAMPTZ NOT NULL DEFAULT now(),
+    finished_at    TIMESTAMPTZ,
+    success_count  INT NOT NULL DEFAULT 0,
+    failure_count  INT NOT NULL DEFAULT 0,
+    skipped_count  INT NOT NULL DEFAULT 0,
+    error_details  JSONB
+  );
+  CREATE INDEX IF NOT EXISTS idx_cron_run_history_kind_started
+    ON cron_run_history (run_kind, started_at DESC);
 `;
 
 let migrated = false;
@@ -2961,3 +2981,197 @@ export async function setInvoiceStripePaymentIntent(
     [invoiceId, paymentIntentId]
   );
 }
+
+// ---------------------------------------------------------------------------
+// Phase 5 — Cron run history + reminder helpers
+// ---------------------------------------------------------------------------
+
+import type { CronRun, CronRunKind } from "@/types";
+
+function rowToCronRun(row: any): CronRun {
+  return {
+    id: row.id,
+    runKind: row.run_kind,
+    triggeredBy: row.triggered_by,
+    startedAt:
+      row.started_at?.toISOString?.() ?? String(row.started_at),
+    finishedAt: row.finished_at
+      ? row.finished_at.toISOString?.() ?? String(row.finished_at)
+      : null,
+    successCount: Number(row.success_count ?? 0),
+    failureCount: Number(row.failure_count ?? 0),
+    skippedCount: Number(row.skipped_count ?? 0),
+    errorDetails: row.error_details ?? null,
+  };
+}
+
+/**
+ * Open a new cron-run row in 'started' state. Returns the row's
+ * id which the caller passes to finishCronRun() with the summary
+ * stats once the sweep completes.
+ *
+ * Separating start/finish lets the admin UI distinguish an in-
+ * progress run from a finished one, and lets a crashed pod leave
+ * a forensic trace ("started but never finished — investigate").
+ */
+export async function startCronRun(
+  runKind: CronRunKind,
+  triggeredBy: string
+): Promise<string> {
+  await ensureSchema();
+  const result = await getPool().query(
+    `INSERT INTO cron_run_history (run_kind, triggered_by)
+     VALUES ($1, $2)
+     RETURNING id`,
+    [runKind, triggeredBy]
+  );
+  return result.rows[0].id;
+}
+
+export async function finishCronRun(
+  id: string,
+  summary: {
+    successCount: number;
+    failureCount: number;
+    skippedCount: number;
+    errorDetails?: unknown;
+  }
+): Promise<void> {
+  await ensureSchema();
+  await getPool().query(
+    `UPDATE cron_run_history
+        SET finished_at = now(),
+            success_count = $2,
+            failure_count = $3,
+            skipped_count = $4,
+            error_details = $5::jsonb
+      WHERE id = $1`,
+    [
+      id,
+      summary.successCount,
+      summary.failureCount,
+      summary.skippedCount,
+      summary.errorDetails ? JSON.stringify(summary.errorDetails) : null,
+    ]
+  );
+}
+
+export async function listRecentCronRuns(
+  limit = 30
+): Promise<CronRun[]> {
+  await ensureSchema();
+  const result = await getPool().query(
+    `SELECT * FROM cron_run_history
+      ORDER BY started_at DESC
+      LIMIT $1`,
+    [limit]
+  );
+  return result.rows.map(rowToCronRun);
+}
+
+/**
+ * Most recent successful run of each kind. Drives the admin
+ * dashboard's "last issuance: N days ago" indicator. Returns
+ * null for a kind that has never run successfully.
+ */
+export async function getLastSuccessfulCronRuns(): Promise<{
+  monthlyIssue: CronRun | null;
+  reminders: CronRun | null;
+}> {
+  await ensureSchema();
+  const result = await getPool().query(
+    `SELECT DISTINCT ON (run_kind) *
+       FROM cron_run_history
+      WHERE finished_at IS NOT NULL AND failure_count = 0
+      ORDER BY run_kind, started_at DESC`
+  );
+  const map: Record<string, CronRun> = {};
+  for (const row of result.rows) {
+    map[row.run_kind] = rowToCronRun(row);
+  }
+  return {
+    monthlyIssue: map["monthly_issue"] ?? null,
+    reminders: map["reminders"] ?? null,
+  };
+}
+
+/**
+ * IDs of all orgs with auto-issue enabled. Drives the monthly
+ * issuance sweep. Returns just the zitadel_org_id strings — the
+ * caller fetches OrgBilling per-org during the sweep so a bad
+ * row doesn't poison the whole list at SELECT time.
+ */
+export async function listAutoIssueOrgIds(): Promise<string[]> {
+  await ensureSchema();
+  const result = await getPool().query(
+    `SELECT zitadel_org_id FROM org_billing_config
+      WHERE auto_invoice_enabled = TRUE`
+  );
+  return result.rows.map((r) => r.zitadel_org_id as string);
+}
+
+/**
+ * Open or overdue invoices whose org has auto-reminders enabled
+ * and whose due_at is at least 7 days in the past. The reminder
+ * sweep takes this list and picks the right level (1/2/3) per
+ * invoice based on days-past-due AND which levels have already
+ * been sent.
+ *
+ * We don't filter by "needs reminder X yet" in SQL because the
+ * level logic is more readable in TypeScript and the candidate
+ * set is small (only past-due invoices for opted-in orgs).
+ */
+export async function listInvoicesPendingReminders(): Promise<Invoice[]> {
+  await ensureSchema();
+  const result = await getPool().query(
+    `SELECT ${INVOICE_LIST_COLUMNS}
+       FROM invoices i
+       JOIN org_billing_config c
+         ON c.zitadel_org_id = i.zitadel_org_id
+        AND c.auto_reminders_enabled = TRUE
+      WHERE i.status IN ('open','overdue')
+        AND i.due_at < now() - INTERVAL '7 days'
+      ORDER BY i.due_at ASC`
+  );
+  return result.rows.map(rowToInvoice);
+}
+
+/**
+ * Which reminder levels have already been sent for this invoice?
+ * Returns a Set of {1, 2, 3} subset. Drives the "send the next
+ * level only" logic in the reminder sweep.
+ */
+export async function getReminderLevelsSent(
+  invoiceId: string
+): Promise<Set<number>> {
+  await ensureSchema();
+  const result = await getPool().query(
+    `SELECT level FROM invoice_reminders WHERE invoice_id = $1`,
+    [invoiceId]
+  );
+  return new Set(result.rows.map((r) => Number(r.level)));
+}
+
+/**
+ * Mark a reminder as sent. Wrapped in an INSERT ... ON CONFLICT
+ * DO NOTHING so a retry of the same level after a partial failure
+ * is a no-op rather than a 23505 explosion. Returns true if a row
+ * was inserted (first send), false on conflict (already sent).
+ */
+export async function recordReminderSent(params: {
+  invoiceId: string;
+  level: 1 | 2 | 3;
+  sentBy: string;
+  emailSentTo: string;
+}): Promise<boolean> {
+  await ensureSchema();
+  const result = await getPool().query(
+    `INSERT INTO invoice_reminders
+       (invoice_id, level, sent_by, email_sent_to)
+     VALUES ($1, $2, $3, $4)
+     ON CONFLICT (invoice_id, level) DO NOTHING
+     RETURNING id`,
+    [params.invoiceId, params.level, params.sentBy, params.emailSentTo]
+  );
+  return result.rowCount === 1;
+}

src/lib/email.ts

@@ -1014,3 +1014,147 @@ export async function sendInvoiceIssuedEmail(params: {
     console.error("Failed to send invoice issued email:", err);
   }
 }
+
+// ---------------------------------------------------------------------------
+// Reminder emails — Phase 5
+// ---------------------------------------------------------------------------
+
+/**
+ * Send a payment reminder for an open/overdue invoice.
+ *
+ * Three escalation levels:
+ *   1 — Gentle nudge: ~7 days past due. Friendly tone, "in case
+ *       you missed it".
+ *   2 — Firmer reminder: ~14 days past due. Clear that payment is
+ *       outstanding, please pay.
+ *   3 — Final notice: ~30 days past due. Explicit consequences
+ *       (service may be suspended). Last automated touch — beyond
+ *       this, admin involvement is expected.
+ *
+ * Failure is logged, never thrown — the cron sweep must continue
+ * past a single failed send.
+ */
+export async function sendInvoiceReminderEmail(params: {
+  to: string;
+  contactName: string;
+  companyName: string;
+  invoiceNumber: string;
+  totalChf: number;
+  currency: string;
+  dueAt: string;
+  daysPastDue: number;
+  level: 1 | 2 | 3;
+  locale: "de" | "en" | "fr" | "it";
+}): Promise<void> {
+  const L = params.locale;
+  // Per-locale strings keyed by the three escalation levels.
+  // Kept inline (rather than the next-intl message files) because
+  // the email layer doesn't import from React's i18n context.
+  const SUBJECTS: Record<typeof L, Record<1 | 2 | 3, string>> = {
+    en: {
+      1: `Friendly reminder: invoice ${params.invoiceNumber} is overdue`,
+      2: `Second reminder: invoice ${params.invoiceNumber} is still unpaid`,
+      3: `Final notice: invoice ${params.invoiceNumber} requires immediate payment`,
+    },
+    de: {
+      1: `Freundliche Erinnerung: Rechnung ${params.invoiceNumber} ist überfällig`,
+      2: `Zweite Mahnung: Rechnung ${params.invoiceNumber} ist weiterhin unbezahlt`,
+      3: `Letzte Mahnung: Rechnung ${params.invoiceNumber} erfordert sofortige Zahlung`,
+    },
+    fr: {
+      1: `Rappel amical : la facture ${params.invoiceNumber} est en retard`,
+      2: `Deuxième rappel : la facture ${params.invoiceNumber} reste impayée`,
+      3: `Dernier avis : la facture ${params.invoiceNumber} doit être réglée sans délai`,
+    },
+    it: {
+      1: `Promemoria amichevole: la fattura ${params.invoiceNumber} è scaduta`,
+      2: `Secondo sollecito: la fattura ${params.invoiceNumber} è ancora insoluta`,
+      3: `Avviso finale: la fattura ${params.invoiceNumber} richiede pagamento immediato`,
+    },
+  };
+  const INTROS: Record<typeof L, Record<1 | 2 | 3, string>> = {
+    en: {
+      1: "We noticed this invoice hasn't been settled yet — in case it slipped through.",
+      2: "This invoice remains unpaid. Please arrange payment at your earliest convenience.",
+      3: "This invoice is significantly overdue. Service may be suspended if payment is not received promptly.",
+    },
+    de: {
+      1: "Diese Rechnung scheint noch nicht beglichen — falls sie übersehen wurde, möchten wir freundlich daran erinnern.",
+      2: "Diese Rechnung ist weiterhin unbezahlt. Bitte veranlassen Sie die Zahlung umgehend.",
+      3: "Diese Rechnung ist erheblich überfällig. Bei nicht zeitnaher Zahlung kann der Dienst ausgesetzt werden.",
+    },
+    fr: {
+      1: "Cette facture n'a pas encore été réglée — au cas où elle vous aurait échappé.",
+      2: "Cette facture reste impayée. Merci d'effectuer le paiement dans les meilleurs délais.",
+      3: "Cette facture est en grand retard. Le service pourra être suspendu en l'absence de paiement rapide.",
+    },
+    it: {
+      1: "Questa fattura non risulta ancora saldata — nel caso vi fosse sfuggita.",
+      2: "Questa fattura risulta ancora insoluta. Si prega di provvedere al pagamento al più presto.",
+      3: "Questa fattura è significativamente in ritardo. In assenza di pagamento tempestivo il servizio potrà essere sospeso.",
+    },
+  };
+  const LABELS: Record<typeof L, Record<string, string>> = {
+    en: { num: "Invoice", total: "Total", due: "Due date", days: "Days past due", cta: "View invoice & pay", signoff: "Best regards", brand: "PieCed IT", greeting: "Hello" },
+    de: { num: "Rechnung", total: "Gesamt", due: "Fälligkeitsdatum", days: "Tage überfällig", cta: "Rechnung ansehen & bezahlen", signoff: "Mit freundlichen Grüssen", brand: "PieCed IT", greeting: "Sehr geehrte/r" },
+    fr: { num: "Facture", total: "Total", due: "Échéance", days: "Jours de retard", cta: "Voir la facture & payer", signoff: "Cordialement", brand: "PieCed IT", greeting: "Bonjour" },
+    it: { num: "Fattura", total: "Totale", due: "Scadenza", days: "Giorni di ritardo", cta: "Vedi fattura & paga", signoff: "Cordiali saluti", brand: "PieCed IT", greeting: "Gentile" },
+  };
+  const l = LABELS[L];
+  const safeName = escapeHtml(params.contactName);
+  const safeCompany = escapeHtml(params.companyName);
+  const safeNumber = escapeHtml(params.invoiceNumber);
+  const totalFmt = `${params.currency} ${params.totalChf.toFixed(2)}`;
+  const dueFmt = params.dueAt.slice(0, 10);
+  const link = `https://app.pieced.ch/billing/${encodeURIComponent(params.invoiceNumber)}`;
+  // Final-notice gets red accent; earlier levels keep the brand green.
+  const accent = params.level === 3 ? "#dc2626" : "#10B981";
+
+  try {
+    await getTransporter().sendMail({
+      from: getFrom(),
+      to: params.to,
+      subject: SUBJECTS[L][params.level],
+      text: [
+        `${l.greeting} ${params.contactName},`,
+        "",
+        INTROS[L][params.level],
+        "",
+        `${l.num}:    ${params.invoiceNumber}`,
+        `${l.total}:    ${totalFmt}`,
+        `${l.due}:    ${dueFmt}`,
+        `${l.days}:    ${params.daysPastDue}`,
+        "",
+        `${l.cta}: ${link}`,
+        "",
+        `${l.signoff},`,
+        l.brand,
+      ].join("\n"),
+      html: `
+        <div style="font-family:-apple-system,BlinkMacSystemFont,sans-serif;max-width:560px;padding:24px;background:#1a1a1a;color:#e5e5e5;">
+          <h2 style="margin:0 0 16px;color:${accent};">${escapeHtml(SUBJECTS[L][params.level])}</h2>
+          <p>${l.greeting} ${safeName},</p>
+          <p>${escapeHtml(INTROS[L][params.level])}</p>
+          <table style="width:100%;border-collapse:collapse;margin:16px 0;font-size:14px;">
+            <tr><td style="color:#888;padding:6px 0;width:140px;">${l.num}</td><td><strong>${safeNumber}</strong></td></tr>
+            <tr><td style="color:#888;padding:6px 0;">${l.total}</td><td style="color:${accent};font-weight:600;">${escapeHtml(totalFmt)}</td></tr>
+            <tr><td style="color:#888;padding:6px 0;">${l.due}</td><td>${escapeHtml(dueFmt)}</td></tr>
+            <tr><td style="color:#888;padding:6px 0;">${l.days}</td><td>${params.daysPastDue}</td></tr>
+          </table>
+          <p>
+            <a href="${link}" style="display:inline-block;padding:10px 24px;background:${accent};color:#fff;text-decoration:none;border-radius:8px;font-weight:500;">
+              ${l.cta}
+            </a>
+          </p>
+          <hr style="border:none;border-top:1px solid #333;margin:24px 0;" />
+          <p style="color:#666;font-size:12px;">${l.brand}</p>
+        </div>
+      `,
+    });
+  } catch (err) {
+    console.error(
+      `Failed to send reminder L${params.level} for invoice ${params.invoiceNumber}:`,
+      err
+    );
+  }
+}

src/messages/de.json

@@ -393,7 +393,8 @@
     "resumeRequestTooltip": "Reaktivierungsanfrage für einen bestehenden Tenant. Bei Genehmigung wird der Tenant wieder aktiviert; keine Provisionierung läuft.",
     "openclawTool": "OpenClaw-Versionen",
     "billingTool": "Abrechnung →",
-    "skillsQueueTool": "Aktivierungs-Warteschlange"
+    "skillsQueueTool": "Aktivierungs-Warteschlange",
+    "cronTool": "Automatisierung"
   },
   "channelUsers": {
     "title": "Autorisierte Benutzer",
@@ -742,5 +743,35 @@
     "redirectingToStripe": "Weiterleitung…",
     "paymentReceived": "Zahlung erhalten — vielen Dank!",
     "paymentCancelled": "Zahlung abgebrochen."
+  },
+  "adminCron": {
+    "title": "Abrechnungsautomatisierung",
+    "subtitle": "Monatliche Rechnungsstellung und tägliche Mahnungsläufe. Beides läuft automatisch; mit den Schaltflächen unten können Sie einen Lauf manuell auslösen.",
+    "monthlyIssue": "Monatliche Rechnungsstellung",
+    "reminders": "Mahnungen",
+    "scheduleIssueLabel": "Zeitplan",
+    "scheduleIssueValue": "00:30 Europe/Zurich am 1.",
+    "scheduleReminderLabel": "Zeitplan",
+    "scheduleReminderValue": "09:00 Europe/Zurich täglich",
+    "lastSuccess": "Letzter Erfolg",
+    "never": "nie",
+    "runIssueNow": "Letzten Monat jetzt abrechnen",
+    "runRemindersNow": "Mahnungslauf jetzt starten",
+    "running": "Läuft…",
+    "flashIssueOk": "Rechnungsstellung abgeschlossen: {success} Rechnungen erstellt, {skipped} übersprungen, {failure} fehlgeschlagen.",
+    "flashRemindersOk": "Mahnungen versendet: {success} erfolgreich, {skipped} übersprungen, {failure} fehlgeschlagen.",
+    "recentRuns": "Letzte Läufe (max. 30)",
+    "noRunsYet": "Noch keine Automatisierungsläufe erfasst.",
+    "startedCol": "Gestartet",
+    "kindCol": "Art",
+    "triggeredByCol": "Ausgelöst von",
+    "okCol": "OK",
+    "skipCol": "Übersprungen",
+    "failCol": "Fehler",
+    "triggeredByCron": "Cron",
+    "kind": {
+      "monthly_issue": "Rechnungsstellung",
+      "reminders": "Mahnungen"
+    }
   }
 }

src/messages/en.json

@@ -393,7 +393,8 @@
     "resumeRequestTooltip": "Reactivation request for an existing tenant. Approving will un-suspend the tenant; no provisioning runs.",
     "openclawTool": "OpenClaw versions",
     "billingTool": "Billing →",
-    "skillsQueueTool": "Activation Queue"
+    "skillsQueueTool": "Activation Queue",
+    "cronTool": "Automation"
   },
   "channelUsers": {
     "title": "Authorized Users",
@@ -742,5 +743,35 @@
     "redirectingToStripe": "Redirecting…",
     "paymentReceived": "Payment received — thank you!",
     "paymentCancelled": "Payment cancelled."
+  },
+  "adminCron": {
+    "title": "Billing automation",
+    "subtitle": "Monthly issuance and daily reminder sweeps. Both run automatically; use the buttons below to trigger a sweep on demand.",
+    "monthlyIssue": "Monthly issuance",
+    "reminders": "Reminders",
+    "scheduleIssueLabel": "Schedule",
+    "scheduleIssueValue": "00:30 Europe/Zurich on the 1st",
+    "scheduleReminderLabel": "Schedule",
+    "scheduleReminderValue": "09:00 Europe/Zurich daily",
+    "lastSuccess": "Last success",
+    "never": "never",
+    "runIssueNow": "Run last month's issuance now",
+    "runRemindersNow": "Run reminder sweep now",
+    "running": "Running…",
+    "flashIssueOk": "Issuance complete: {success} invoices issued, {skipped} skipped, {failure} failed.",
+    "flashRemindersOk": "Reminders sent: {success} succeeded, {skipped} skipped, {failure} failed.",
+    "recentRuns": "Recent runs (last 30)",
+    "noRunsYet": "No automation runs recorded yet.",
+    "startedCol": "Started",
+    "kindCol": "Kind",
+    "triggeredByCol": "Triggered by",
+    "okCol": "OK",
+    "skipCol": "Skipped",
+    "failCol": "Failed",
+    "triggeredByCron": "cron",
+    "kind": {
+      "monthly_issue": "Issuance",
+      "reminders": "Reminders"
+    }
   }
 }

src/messages/fr.json

@@ -393,7 +393,8 @@
     "resumeRequestTooltip": "Demande de réactivation d'un locataire existant. L'approbation le réactivera ; aucun provisionnement ne s'exécute.",
     "openclawTool": "Versions OpenClaw",
     "billingTool": "Facturation →",
-    "skillsQueueTool": "File d'activation"
+    "skillsQueueTool": "File d'activation",
+    "cronTool": "Automatisation"
   },
   "channelUsers": {
     "title": "Utilisateurs autorisés",
@@ -742,5 +743,35 @@
     "redirectingToStripe": "Redirection…",
     "paymentReceived": "Paiement reçu — merci !",
     "paymentCancelled": "Paiement annulé."
+  },
+  "adminCron": {
+    "title": "Automatisation de la facturation",
+    "subtitle": "Émission mensuelle et balayage quotidien des rappels. Les deux s'exécutent automatiquement ; utilisez les boutons ci-dessous pour déclencher un lancement à la demande.",
+    "monthlyIssue": "Émission mensuelle",
+    "reminders": "Rappels",
+    "scheduleIssueLabel": "Planning",
+    "scheduleIssueValue": "00:30 Europe/Zurich le 1er",
+    "scheduleReminderLabel": "Planning",
+    "scheduleReminderValue": "09:00 Europe/Zurich quotidien",
+    "lastSuccess": "Dernière réussite",
+    "never": "jamais",
+    "runIssueNow": "Facturer le mois dernier maintenant",
+    "runRemindersNow": "Lancer les rappels maintenant",
+    "running": "En cours…",
+    "flashIssueOk": "Émission terminée : {success} factures émises, {skipped} ignorées, {failure} échouées.",
+    "flashRemindersOk": "Rappels envoyés : {success} réussis, {skipped} ignorés, {failure} échoués.",
+    "recentRuns": "Lancements récents (30 derniers)",
+    "noRunsYet": "Aucun lancement automatique enregistré pour le moment.",
+    "startedCol": "Démarré",
+    "kindCol": "Type",
+    "triggeredByCol": "Déclenché par",
+    "okCol": "OK",
+    "skipCol": "Ignorés",
+    "failCol": "Échoués",
+    "triggeredByCron": "cron",
+    "kind": {
+      "monthly_issue": "Émission",
+      "reminders": "Rappels"
+    }
   }
 }

src/messages/it.json

@@ -393,7 +393,8 @@
     "resumeRequestTooltip": "Richiesta di riattivazione di un tenant esistente. L'approvazione lo riattiverà; non viene eseguito alcun provisioning.",
     "openclawTool": "Versioni OpenClaw",
     "billingTool": "Fatturazione →",
-    "skillsQueueTool": "Coda di attivazione"
+    "skillsQueueTool": "Coda di attivazione",
+    "cronTool": "Automazione"
   },
   "channelUsers": {
     "title": "Utenti autorizzati",
@@ -742,5 +743,35 @@
     "redirectingToStripe": "Reindirizzamento…",
     "paymentReceived": "Pagamento ricevuto — grazie!",
     "paymentCancelled": "Pagamento annullato."
+  },
+  "adminCron": {
+    "title": "Automazione fatturazione",
+    "subtitle": "Emissione mensile e invio quotidiano dei solleciti. Entrambi vengono eseguiti automaticamente; usa i pulsanti sotto per avviare un'esecuzione su richiesta.",
+    "monthlyIssue": "Emissione mensile",
+    "reminders": "Solleciti",
+    "scheduleIssueLabel": "Pianificazione",
+    "scheduleIssueValue": "00:30 Europe/Zurich il 1°",
+    "scheduleReminderLabel": "Pianificazione",
+    "scheduleReminderValue": "09:00 Europe/Zurich quotidianamente",
+    "lastSuccess": "Ultimo successo",
+    "never": "mai",
+    "runIssueNow": "Fattura il mese scorso ora",
+    "runRemindersNow": "Avvia solleciti ora",
+    "running": "In corso…",
+    "flashIssueOk": "Emissione completata: {success} fatture emesse, {skipped} ignorate, {failure} fallite.",
+    "flashRemindersOk": "Solleciti inviati: {success} riusciti, {skipped} ignorati, {failure} falliti.",
+    "recentRuns": "Esecuzioni recenti (ultime 30)",
+    "noRunsYet": "Nessuna esecuzione automatica registrata.",
+    "startedCol": "Avviata",
+    "kindCol": "Tipo",
+    "triggeredByCol": "Avviata da",
+    "okCol": "OK",
+    "skipCol": "Ignorati",
+    "failCol": "Falliti",
+    "triggeredByCron": "cron",
+    "kind": {
+      "monthly_issue": "Emissione",
+      "reminders": "Solleciti"
+    }
   }
 }

src/types/index.ts

@@ -542,6 +542,20 @@ export type InvoiceStatus =
 
 export type InvoicePaymentMethod = "invoice" | "card";
 
+// Phase 5 — Cron run history rows for the admin /admin/cron page.
+export type CronRunKind = "monthly_issue" | "reminders";
+export interface CronRun {
+  id: string;
+  runKind: CronRunKind;
+  triggeredBy: string;
+  startedAt: string;
+  finishedAt: string | null;
+  successCount: number;
+  failureCount: number;
+  skippedCount: number;
+  errorDetails: unknown | null;
+}
+
 export type InvoiceLineKind =
   | "tenant_monthly"
   | "tenant_setup"