fix(api): harden reminder and webhook delivery

packages/api/src/__tests__/reminder-scheduler.test.ts

@@ -0,0 +1,179 @@
+import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
+import { emitNotificationCreated, emitReminderDue } from "../sse/event-bus.js";
+import { logger } from "../lib/logger.js";
+import { startReminderScheduler, stopReminderScheduler } from "../lib/reminder-scheduler.js";
+
+const { findMany, create, update } = vi.hoisted(() => ({
+  findMany: vi.fn(),
+  create: vi.fn(),
+  update: vi.fn(),
+}));
+
+vi.mock("@capakraken/db", () => ({
+  prisma: {
+    notification: {
+      findMany,
+      create,
+      update,
+    },
+  },
+}));
+
+vi.mock("../sse/event-bus.js", () => ({
+  emitReminderDue: vi.fn(),
+  emitNotificationCreated: vi.fn(),
+}));
+
+vi.mock("../lib/logger.js", () => ({
+  logger: {
+    error: vi.fn(),
+    warn: vi.fn(),
+    info: vi.fn(),
+    debug: vi.fn(),
+  },
+}));
+
+describe("reminder scheduler logging", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+    vi.useRealTimers();
+    findMany.mockResolvedValue([]);
+    create.mockResolvedValue({ id: "notification_1" });
+    update.mockResolvedValue({});
+  });
+
+  afterEach(() => {
+    stopReminderScheduler();
+  });
+
+  it("logs scheduler lifecycle with structured metadata", async () => {
+    startReminderScheduler();
+
+    await vi.waitFor(() => {
+      expect(findMany).toHaveBeenCalled();
+    });
+
+    expect(logger.info).toHaveBeenCalledWith(
+      { pollIntervalMs: 60_000 },
+      "Starting reminder scheduler",
+    );
+
+    stopReminderScheduler();
+
+    expect(logger.info).toHaveBeenCalledWith("Stopped reminder scheduler");
+  });
+
+  it("logs reminder processing failures with reminder context", async () => {
+    findMany.mockResolvedValueOnce([
+      {
+        id: "reminder_1",
+        userId: "user_1",
+        recurrence: null,
+        priority: "HIGH",
+        title: "Follow up",
+        body: "Body",
+        entityId: null,
+        entityType: null,
+        link: null,
+        nextRemindAt: new Date("2026-03-30T08:00:00.000Z"),
+      },
+    ]);
+    update.mockRejectedValueOnce(new Error("db write failed"));
+
+    startReminderScheduler();
+
+    await vi.waitFor(() => {
+      expect(logger.error).toHaveBeenCalledWith(
+        {
+          err: expect.any(Error),
+          reminderId: "reminder_1",
+          userId: "user_1",
+        },
+        "Failed to process reminder",
+      );
+    });
+
+    expect(emitReminderDue).not.toHaveBeenCalled();
+    expect(emitNotificationCreated).not.toHaveBeenCalled();
+  });
+
+  it("does not start a second reminder poll while the previous batch is still running", async () => {
+    vi.useFakeTimers();
+
+    let releaseFindMany: ((value: unknown[]) => void) | null = null;
+    findMany.mockImplementationOnce(
+      () =>
+        new Promise((resolve) => {
+          releaseFindMany = resolve;
+        }),
+    );
+
+    startReminderScheduler();
+
+    expect(findMany).toHaveBeenCalledTimes(1);
+
+    await vi.advanceTimersByTimeAsync(60_000);
+
+    expect(findMany).toHaveBeenCalledTimes(1);
+    expect(logger.warn).toHaveBeenCalledWith(
+      "Skipping reminder scheduler tick while previous run is still processing",
+    );
+
+    releaseFindMany?.([]);
+    await Promise.resolve();
+
+    await vi.advanceTimersByTimeAsync(60_000);
+
+    expect(findMany).toHaveBeenCalledTimes(2);
+  });
+
+  it("advances overdue recurring reminders to the first occurrence after now", async () => {
+    const now = new Date();
+    const staleNextRemindAt = new Date(now);
+    staleNextRemindAt.setDate(staleNextRemindAt.getDate() - 3);
+    staleNextRemindAt.setHours(8, 0, 0, 0);
+
+    const expectedNextRemindAt = new Date(staleNextRemindAt);
+    while (expectedNextRemindAt.getTime() <= now.getTime()) {
+      expectedNextRemindAt.setDate(expectedNextRemindAt.getDate() + 1);
+    }
+
+    const overdueReminder = {
+      id: "reminder_recurring_1",
+      userId: "user_1",
+      recurrence: "daily",
+      priority: "MEDIUM",
+      title: "Daily standup prep",
+      body: "Body",
+      entityId: null,
+      entityType: null,
+      link: null,
+      nextRemindAt: staleNextRemindAt,
+    };
+
+    findMany.mockResolvedValueOnce([overdueReminder]);
+
+    startReminderScheduler();
+
+    await vi.waitFor(() => {
+      expect(create).toHaveBeenCalledWith(
+        expect.objectContaining({
+          data: expect.objectContaining({
+            userId: "user_1",
+            sourceId: "reminder_recurring_1",
+            type: "REMINDER_DUE",
+          }),
+        }),
+      );
+    });
+
+    expect(update).toHaveBeenCalledWith({
+      where: { id: "reminder_recurring_1" },
+      data: {
+        nextRemindAt: expectedNextRemindAt,
+      },
+    });
+    expect(emitNotificationCreated).toHaveBeenCalledWith("user_1", "notification_1");
+    expect(emitReminderDue).toHaveBeenCalledWith("user_1", "notification_1");
+  });
+});

packages/api/src/__tests__/webhook-dispatcher.test.ts

@@ -0,0 +1,122 @@
+import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
+import { logger } from "../lib/logger.js";
+import { dispatchWebhooks } from "../lib/webhook-dispatcher.js";
+
+const { sendSlackNotification } = vi.hoisted(() => ({
+  sendSlackNotification: vi.fn(),
+}));
+
+vi.mock("../lib/slack-notify.js", () => ({
+  sendSlackNotification,
+}));
+
+vi.mock("../lib/logger.js", () => ({
+  logger: {
+    error: vi.fn(),
+    warn: vi.fn(),
+    info: vi.fn(),
+    debug: vi.fn(),
+  },
+}));
+
+describe("webhook dispatcher logging", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+  });
+
+  afterEach(() => {
+    vi.unstubAllGlobals();
+  });
+
+  it("logs dispatcher-level failures with event context", async () => {
+    const db = {
+      webhook: {
+        findMany: vi.fn().mockRejectedValue(new Error("database unavailable")),
+      },
+    };
+
+    dispatchWebhooks(db, "estimate.submitted", { id: "estimate_1" });
+
+    await vi.waitFor(() => {
+      expect(logger.error).toHaveBeenCalledWith(
+        {
+          err: expect.any(Error),
+          event: "estimate.submitted",
+        },
+        "Failed to dispatch webhooks",
+      );
+    });
+  });
+
+  it("logs webhook delivery failures with webhook metadata", async () => {
+    sendSlackNotification.mockRejectedValueOnce(new Error("slack down"));
+
+    const db = {
+      webhook: {
+        findMany: vi.fn().mockResolvedValue([
+          {
+            id: "wh_1",
+            name: "Ops Slack",
+            url: "https://hooks.slack.com/services/test",
+            secret: null,
+            events: ["project.created"],
+          },
+        ]),
+      },
+    };
+
+    dispatchWebhooks(db, "project.created", { id: "project_1", name: "Project One" });
+
+    await vi.waitFor(() => {
+      expect(logger.warn).toHaveBeenCalledWith(
+        {
+          err: expect.any(Error),
+          event: "project.created",
+          webhookId: "wh_1",
+          webhookName: "Ops Slack",
+          webhookUrl: "https://hooks.slack.com/services/test",
+        },
+        "Webhook delivery failed",
+      );
+    });
+  });
+
+  it("treats non-2xx HTTP webhook responses as delivery failures", async () => {
+    const fetchMock = vi.fn().mockResolvedValue({
+      ok: false,
+      status: 500,
+    });
+    vi.stubGlobal("fetch", fetchMock);
+
+    const db = {
+      webhook: {
+        findMany: vi.fn().mockResolvedValue([
+          {
+            id: "wh_http_1",
+            name: "Project Webhook",
+            url: "https://example.com/webhooks/project",
+            secret: "secret",
+            events: ["project.created"],
+          },
+        ]),
+      },
+    };
+
+    dispatchWebhooks(db, "project.created", { id: "project_1", name: "Project One" });
+
+    await vi.waitFor(() => {
+      expect(logger.warn).toHaveBeenCalledWith(
+        {
+          err: expect.any(Error),
+          event: "project.created",
+          webhookId: "wh_http_1",
+          webhookName: "Project Webhook",
+          webhookUrl: "https://example.com/webhooks/project",
+        },
+        "Webhook delivery failed",
+      );
+    });
+
+    expect(fetchMock).toHaveBeenCalledTimes(1);
+  });
+});

packages/api/src/lib/reminder-scheduler.ts

@@ -1,7 +1,9 @@
 import { prisma } from "@capakraken/db";
+import { logger } from "./logger.js";
 import { emitReminderDue, emitNotificationCreated } from "../sse/event-bus.js";
 
 const POLL_INTERVAL_MS = 60_000; // 60 seconds
+let isProcessing = false;
 
 function computeNextRemindAt(current: Date, recurrence: string): Date {
   const next = new Date(current);
@@ -21,61 +23,95 @@ function computeNextRemindAt(current: Date, recurrence: string): Date {
   return next;
 }
 
+function computeNextRemindAtAfter(current: Date, recurrence: string, now: Date): Date {
+  let next = computeNextRemindAt(current, recurrence);
+  if (next.getTime() <= current.getTime()) {
+    return current;
+  }
+
+  while (next.getTime() <= now.getTime()) {
+    const advanced = computeNextRemindAt(next, recurrence);
+    if (advanced.getTime() <= next.getTime()) {
+      return next;
+    }
+    next = advanced;
+  }
+
+  return next;
+}
+
 async function processReminders() {
+  if (isProcessing) {
+    logger.warn("Skipping reminder scheduler tick while previous run is still processing");
+    return;
+  }
+
+  isProcessing = true;
   const now = new Date();
 
-  // Find all due reminders
-  const dueReminders = await prisma.notification.findMany({
-    where: {
-      category: "REMINDER",
-      nextRemindAt: { lte: now },
-    },
-    take: 100, // process in batches
-  });
+  try {
+    // Find all due reminders
+    const dueReminders = await prisma.notification.findMany({
+      where: {
+        category: "REMINDER",
+        nextRemindAt: { lte: now },
+      },
+      take: 100, // process in batches
+    });
 
-  for (const reminder of dueReminders) {
-    try {
-      if (reminder.recurrence) {
-        // Recurring: create a new notification for this occurrence, advance nextRemindAt
-        const notification = await prisma.notification.create({
-          data: {
-            userId: reminder.userId,
-            category: "NOTIFICATION",
-            type: "REMINDER_DUE",
-            priority: reminder.priority,
-            title: reminder.title,
-            body: reminder.body,
-            entityId: reminder.entityId,
-            entityType: reminder.entityType,
-            link: reminder.link,
-            sourceId: reminder.id,
-            channel: "in_app",
-          },
-        });
+    for (const reminder of dueReminders) {
+      try {
+        if (reminder.recurrence) {
+          // Recurring: create a new notification for this occurrence, advance nextRemindAt
+          const notification = await prisma.notification.create({
+            data: {
+              userId: reminder.userId,
+              category: "NOTIFICATION",
+              type: "REMINDER_DUE",
+              priority: reminder.priority,
+              title: reminder.title,
+              body: reminder.body,
+              entityId: reminder.entityId,
+              entityType: reminder.entityType,
+              link: reminder.link,
+              sourceId: reminder.id,
+              channel: "in_app",
+            },
+          });
 
-        // Advance to next occurrence
-        await prisma.notification.update({
-          where: { id: reminder.id },
-          data: {
-            nextRemindAt: computeNextRemindAt(reminder.nextRemindAt!, reminder.recurrence),
-          },
-        });
+          // Advance to next occurrence
+          await prisma.notification.update({
+            where: { id: reminder.id },
+            data: {
+              nextRemindAt: computeNextRemindAtAfter(
+                reminder.nextRemindAt!,
+                reminder.recurrence,
+                now,
+              ),
+            },
+          });
 
-        emitNotificationCreated(reminder.userId, notification.id);
-        emitReminderDue(reminder.userId, notification.id);
-      } else {
-        // One-shot: mark the reminder as "fired" by clearing nextRemindAt
-        await prisma.notification.update({
-          where: { id: reminder.id },
-          data: { nextRemindAt: null },
-        });
+          emitNotificationCreated(reminder.userId, notification.id);
+          emitReminderDue(reminder.userId, notification.id);
+        } else {
+          // One-shot: mark the reminder as "fired" by clearing nextRemindAt
+          await prisma.notification.update({
+            where: { id: reminder.id },
+            data: { nextRemindAt: null },
+          });
 
-        emitReminderDue(reminder.userId, reminder.id);
-        emitNotificationCreated(reminder.userId, reminder.id);
+          emitReminderDue(reminder.userId, reminder.id);
+          emitNotificationCreated(reminder.userId, reminder.id);
+        }
+      } catch (err) {
+        logger.error(
+          { err, reminderId: reminder.id, userId: reminder.userId },
+          "Failed to process reminder",
+        );
       }
-    } catch (err) {
-      console.error(`[ReminderScheduler] Error processing reminder ${reminder.id}:`, err);
     }
+  } finally {
+    isProcessing = false;
   }
 }
 
@@ -83,7 +119,7 @@ let intervalId: ReturnType<typeof setInterval> | null = null;
 
 export function startReminderScheduler(): void {
   if (intervalId) return; // already running
-  console.log("[ReminderScheduler] Starting (poll every 60s)");
+  logger.info({ pollIntervalMs: POLL_INTERVAL_MS }, "Starting reminder scheduler");
   // Run immediately to catch up on overdue reminders
   void processReminders();
   intervalId = setInterval(() => void processReminders(), POLL_INTERVAL_MS);
@@ -93,6 +129,7 @@ export function stopReminderScheduler(): void {
   if (intervalId) {
     clearInterval(intervalId);
     intervalId = null;
-    console.log("[ReminderScheduler] Stopped");
+    isProcessing = false;
+    logger.info("Stopped reminder scheduler");
   }
 }

packages/api/src/lib/webhook-dispatcher.ts

@@ -7,6 +7,7 @@
  * Fire-and-forget — errors are logged, never thrown.
  */
 import { createHmac } from "node:crypto";
+import { logger } from "./logger.js";
 import { sendSlackNotification } from "./slack-notify.js";
 
 /** Available webhook event types. */
@@ -72,7 +73,7 @@ async function _dispatch(
 
     await Promise.allSettled(promises);
   } catch (err) {
-    console.error("[webhook-dispatcher] failed to dispatch:", err);
+    logger.error({ err, event }, "Failed to dispatch webhooks");
   }
 }
 
@@ -108,19 +109,23 @@ async function _sendToWebhook(
     const timeout = setTimeout(() => controller.abort(), 5_000);
 
     try {
-      await fetch(wh.url, {
+      const response = await fetch(wh.url, {
         method: "POST",
         headers,
         body,
         signal: controller.signal,
       });
+
+      if (!response.ok) {
+        throw new Error(`Webhook responded with HTTP ${response.status}`);
+      }
     } finally {
       clearTimeout(timeout);
     }
   } catch (err) {
-    console.error(
-      `[webhook-dispatcher] error sending to "${wh.name}" (${wh.id}):`,
-      err,
+    logger.warn(
+      { err, event, webhookId: wh.id, webhookName: wh.name, webhookUrl: wh.url },
+      "Webhook delivery failed",
     );
   }
 }