fix(02): populate hasRrule on every sync upsert so recurring masters are flagged

- Use ICAL.Event.isRecurring() (parity with expand.ts) to detect RRULE/RDATE
- Add hasRrule to .values() INSERT and .onDuplicateKeyUpdate() SET so the flag
  is set on first sync and self-heals on every subsequent re-sync
- Without this fix every event had has_rrule=0 (column default), causing the
  events route recurring-master pre-filter to return zero recurring occurrences
- Add sync.test.ts cases: hasRrule=true for timed+all-day recurring VEVENTs,
  hasRrule=false for non-recurring, and hasRrule in onDuplicateKeyUpdate.set

apps/api/src/broker/sync.ts

@@ -89,6 +89,10 @@ export async function syncCalendar(
     // D-13 / Pitfall #3: isDate=true → DATE column; isDate=false → TIMESTAMP column
     const allDay: boolean = dtstart?.isDate ?? false
 
+    // Determine if this event is a recurring master (has RRULE or RDATE).
+    // Use ICAL.Event.isRecurring() for parity with expand.ts — it checks both properties.
+    const isRecurring: boolean = new ICAL.Event(vevent).isRecurring()
+
     // dtstartDate: Drizzle's `date` column accepts a Date object or null.
     // We convert the YYYY-MM-DD string from ical.js to a Date (at midnight UTC) so
     // Drizzle serialises it correctly as a DATE without a time component.
@@ -106,6 +110,7 @@ export async function syncCalendar(
         dtstartUtc: dtstartUtcValue,
         dtstartDate: dtstartDateValue,
         allDay,
+        hasRrule: isRecurring,
       })
       .onDuplicateKeyUpdate({
         set: {
@@ -114,6 +119,7 @@ export async function syncCalendar(
           dtstartUtc: dtstartUtcValue,
           dtstartDate: dtstartDateValue,
           allDay,
+          hasRrule: isRecurring,
           updatedAt: new Date(),
         },
       })

apps/api/tests/broker/sync.test.ts

@@ -14,6 +14,8 @@ import { describe, it, expect, vi, beforeEach } from 'vitest'
 import {
   SAMPLE_VEVENT_TIMED,
   SAMPLE_VEVENT_ALLDAY,
+  SAMPLE_VEVENT_RECURRING_TIMED,
+  SAMPLE_VEVENT_RECURRING_ALLDAY,
 } from '../helpers/db.js'
 
 // Track calls for assertions
@@ -157,6 +159,94 @@ describe('syncCalendar', () => {
     expect(eventArg.rawVevent).toBe(SAMPLE_VEVENT_TIMED)
   })
 
+  it('sets hasRrule=true for a VEVENT with RRULE (timed recurring)', async () => {
+    const { syncCalendar } = await import('../../src/broker/sync.js')
+
+    const mockClient = {
+      fetchCalendarObjects: vi.fn().mockResolvedValue([
+        { data: SAMPLE_VEVENT_RECURRING_TIMED, etag: '"etag-rrule"', url: '/rrule.ics' },
+      ]),
+    }
+    const mockDavCal = {
+      url: 'https://caldav.fastmail.com/dav/calendars/user/test@fm.com/Default/',
+      displayName: 'Test Calendar',
+      ctag: 'ctag-v1',
+      syncToken: null,
+    }
+
+    await syncCalendar(mockClient as never, mockDavCal as never, 1)
+
+    expect(mockInsert).toHaveBeenCalledTimes(2)
+    const eventValuesArg = mockValues.mock.calls[1][0]
+    expect(eventValuesArg.hasRrule).toBe(true)
+  })
+
+  it('sets hasRrule=true for an all-day VEVENT with RRULE (all-day recurring)', async () => {
+    const { syncCalendar } = await import('../../src/broker/sync.js')
+
+    const mockClient = {
+      fetchCalendarObjects: vi.fn().mockResolvedValue([
+        { data: SAMPLE_VEVENT_RECURRING_ALLDAY, etag: '"etag-rrule-allday"', url: '/rrule-allday.ics' },
+      ]),
+    }
+    const mockDavCal = {
+      url: 'https://caldav.fastmail.com/dav/calendars/user/test@fm.com/Default/',
+      displayName: 'Test Calendar',
+      ctag: 'ctag-v1',
+      syncToken: null,
+    }
+
+    await syncCalendar(mockClient as never, mockDavCal as never, 1)
+
+    expect(mockInsert).toHaveBeenCalledTimes(2)
+    const eventValuesArg = mockValues.mock.calls[1][0]
+    expect(eventValuesArg.hasRrule).toBe(true)
+  })
+
+  it('sets hasRrule=false for a non-recurring timed VEVENT', async () => {
+    const { syncCalendar } = await import('../../src/broker/sync.js')
+
+    const mockClient = {
+      fetchCalendarObjects: vi.fn().mockResolvedValue([
+        { data: SAMPLE_VEVENT_TIMED, etag: '"etag-oneoff"', url: '/oneoff.ics' },
+      ]),
+    }
+    const mockDavCal = {
+      url: 'https://caldav.fastmail.com/dav/calendars/user/test@fm.com/Default/',
+      displayName: 'Test Calendar',
+      ctag: 'ctag-v1',
+      syncToken: null,
+    }
+
+    await syncCalendar(mockClient as never, mockDavCal as never, 1)
+
+    expect(mockInsert).toHaveBeenCalledTimes(2)
+    const eventValuesArg = mockValues.mock.calls[1][0]
+    expect(eventValuesArg.hasRrule).toBe(false)
+  })
+
+  it('includes hasRrule in onDuplicateKeyUpdate set so re-syncs self-heal the flag', async () => {
+    const { syncCalendar } = await import('../../src/broker/sync.js')
+
+    const mockClient = {
+      fetchCalendarObjects: vi.fn().mockResolvedValue([
+        { data: SAMPLE_VEVENT_RECURRING_TIMED, etag: '"etag-v2"', url: '/rrule.ics' },
+      ]),
+    }
+    const mockDavCal = {
+      url: 'https://caldav.fastmail.com/dav/calendars/user/test@fm.com/Default/',
+      displayName: 'Test Calendar',
+      ctag: 'ctag-v2',
+      syncToken: null,
+    }
+
+    await syncCalendar(mockClient as never, mockDavCal as never, 1)
+
+    // The second onDuplicateKeyUpdate call is for the event upsert
+    const eventUpdateArg = mockOnDuplicateKeyUpdate.mock.calls[1][0]
+    expect(eventUpdateArg.set).toHaveProperty('hasRrule', true)
+  })
+
   it('updates the calendar ctag/syncToken after a successful sync', async () => {
     const { syncCalendar } = await import('../../src/broker/sync.js')
 

apps/api/tests/helpers/db.ts

@@ -57,3 +57,34 @@ DTEND;VALUE=DATE:20260616
 SUMMARY:Test All-Day Event
 END:VEVENT
 END:VCALENDAR`
+
+/**
+ * Sample VEVENT string — a timed recurring event (RRULE:FREQ=WEEKLY).
+ * Used to test that sync sets hasRrule=true for recurring events.
+ */
+export const SAMPLE_VEVENT_RECURRING_TIMED = `BEGIN:VCALENDAR
+VERSION:2.0
+PRODID:-//FamilySync//Test//EN
+BEGIN:VEVENT
+UID:test-recurring-timed-001@familysync
+DTSTART:20240101T100000Z
+RRULE:FREQ=WEEKLY;BYDAY=MO
+SUMMARY:Weekly Monday Meeting
+END:VEVENT
+END:VCALENDAR`
+
+/**
+ * Sample VEVENT string — an all-day recurring event (RRULE:FREQ=YEARLY).
+ * Used to test that sync sets hasRrule=true for all-day recurring events,
+ * and that the events route returns occurrences even when dtstartUtc is NULL.
+ */
+export const SAMPLE_VEVENT_RECURRING_ALLDAY = `BEGIN:VCALENDAR
+VERSION:2.0
+PRODID:-//FamilySync//Test//EN
+BEGIN:VEVENT
+UID:test-recurring-allday-001@familysync
+DTSTART;VALUE=DATE:20240615
+RRULE:FREQ=YEARLY
+SUMMARY:Annual Birthday
+END:VEVENT
+END:VCALENDAR`