fix(lunch): reminder filter, recap failure surfacing, manual send-reminders

- Extract selectUnpickedAttendees helper with OR filter (is null OR pickedAt null)
  to fix cron missing attendees with no MemberLunchPick row at all
- Update cron route to use the helper
- sendRecap now throws TRPCError on email failure instead of silently stamping success
- Add lunch.sendReminders adminProcedure for manual on-demand reminder sends
- Add "Send reminders now" AlertDialog button to LunchRecapActions
- Tests: lunch-reminder-filter.test.ts (2 new), all 5 lunch test files pass (40 tests)

Co-Authored-By: Claude Opus 4.8 (1M context) <noreply@anthropic.com>

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

@@ -1,6 +1,7 @@
 import { NextResponse, type NextRequest } from 'next/server'
 import { prisma } from '@/lib/prisma'
 import { sendLunchReminderEmail } from '@/lib/email'
+import { selectUnpickedAttendees } from '@/server/services/lunch-reminders'
 
 /**
  * Cron: send a single reminder email per attending member who hasn't picked
@@ -35,16 +36,7 @@ export async function GET(request: NextRequest): Promise<NextResponse> {
       )
       if (now < reminderAt || now >= deadline) continue
 
-      const ams = await prisma.attendingMember.findMany({
-        where: {
-          confirmation: {
-            project: { programId: event.programId },
-            status: 'CONFIRMED',
-          },
-          lunchPick: { is: { pickedAt: null } },
-        },
-        include: { user: { select: { name: true, email: true } } },
-      })
+      const ams = await selectUnpickedAttendees(prisma, event)
       for (const am of ams) {
         if (!am.user.email) continue
         try {

src/components/admin/logistics/lunch-recap-actions.tsx

@@ -11,15 +11,28 @@ import {
   DialogTitle,
   DialogFooter,
 } from '@/components/ui/dialog'
-import { Send, Eye } from 'lucide-react'
+import {
+  AlertDialog,
+  AlertDialogAction,
+  AlertDialogCancel,
+  AlertDialogContent,
+  AlertDialogDescription,
+  AlertDialogFooter,
+  AlertDialogHeader,
+  AlertDialogTitle,
+  AlertDialogTrigger,
+} from '@/components/ui/alert-dialog'
+import { Send, Eye, Bell } from 'lucide-react'
 import { toast } from 'sonner'
 
 export function LunchRecapActions({
   programId,
+  lunchEventId,
   recapSentAt,
   extraRecipientCount,
 }: {
   programId: string
+  lunchEventId: string
   recapSentAt: Date | null
   extraRecipientCount: number
 }) {
@@ -46,6 +59,15 @@ export function LunchRecapActions({
     },
   })
 
+  const sendReminders = trpc.lunch.sendReminders.useMutation({
+    onSuccess: (data) => {
+      toast.success(`Reminders sent to ${data.sent} attendee${data.sent === 1 ? '' : 's'}`)
+    },
+    onError: (e) => {
+      toast.error(`Failed to send reminders: ${e.message}`)
+    },
+  })
+
   const { data: preview, isLoading: loadingPreview } =
     trpc.lunch.getRecapPreview.useQuery(
       { programId },
@@ -68,6 +90,31 @@ export function LunchRecapActions({
           >
             <Send className="mr-2 h-4 w-4" /> Send recap now
           </Button>
+          <AlertDialog>
+            <AlertDialogTrigger asChild>
+              <Button variant="outline" disabled={sendReminders.isPending}>
+                <Bell className="mr-2 h-4 w-4" /> Send reminders now
+              </Button>
+            </AlertDialogTrigger>
+            <AlertDialogContent>
+              <AlertDialogHeader>
+                <AlertDialogTitle>Send lunch pick reminders?</AlertDialogTitle>
+                <AlertDialogDescription>
+                  This will send a reminder email to all confirmed attendees who
+                  haven&apos;t picked a lunch dish yet. You can do this multiple
+                  times — it won&apos;t affect the automatic reminder window.
+                </AlertDialogDescription>
+              </AlertDialogHeader>
+              <AlertDialogFooter>
+                <AlertDialogCancel>Cancel</AlertDialogCancel>
+                <AlertDialogAction
+                  onClick={() => sendReminders.mutate({ lunchEventId })}
+                >
+                  Send reminders
+                </AlertDialogAction>
+              </AlertDialogFooter>
+            </AlertDialogContent>
+          </AlertDialog>
         </div>
         <p className="text-muted-foreground text-xs">
           {recapSentAt

src/components/admin/logistics/lunch-tab.tsx

@@ -32,6 +32,7 @@ export function LunchTab({ programId }: { programId: string }) {
           />
           <LunchRecapActions
             programId={programId}
+            lunchEventId={event.id}
             recapSentAt={event.recapSentAt}
             extraRecipientCount={event.extraRecipients.length}
           />

src/server/routers/lunch.ts

@@ -3,7 +3,8 @@ import { TRPCError } from '@trpc/server'
 import { router, adminProcedure, protectedProcedure } from '../trpc'
 import { logAudit } from '../utils/audit'
 import { buildManifest, buildRecapPayload } from '../services/lunch-recap'
-import { sendLunchRecapEmail } from '@/lib/email'
+import { selectUnpickedAttendees } from '../services/lunch-reminders'
+import { sendLunchRecapEmail, sendLunchReminderEmail } from '@/lib/email'
 import { csvCell } from '@/lib/csv'
 
 // ─── Shared zod schemas ──────────────────────────────────────────────────────
@@ -346,7 +347,11 @@ export const lunchRouter = router({
         await sendLunchRecapEmail(recipients, payload)
       } catch (e) {
         console.error('[lunch.sendRecap] email send failed', e)
-        // Continue — we still stamp recapSentAt and audit so admins see what happened.
+        throw new TRPCError({
+          code: 'INTERNAL_SERVER_ERROR',
+          message: `Recap email failed to send: ${e instanceof Error ? e.message : String(e)}`,
+          cause: e,
+        })
       }
       const updated = await ctx.prisma.lunchEvent.update({
         where: { programId: input.programId },
@@ -570,6 +575,45 @@ export const lunchRouter = router({
       return pick
     }),
 
+  /**
+   * Manually send lunch pick reminders to all unpicked attendees for a given
+   * LunchEvent.  Unlike the cron, this does NOT gate on reminderSentAt and does
+   * NOT stamp it — manual sends are repeatable.  Returns { sent } count.
+   */
+  sendReminders: adminProcedure
+    .input(z.object({ lunchEventId: z.string() }))
+    .mutation(async ({ ctx, input }) => {
+      const event = await ctx.prisma.lunchEvent.findUnique({
+        where: { id: input.lunchEventId },
+      })
+      if (!event) throw new TRPCError({ code: 'NOT_FOUND', message: 'Lunch event not found' })
+
+      const ams = await selectUnpickedAttendees(ctx.prisma, event)
+
+      const deadline = event.eventAt
+        ? new Date(event.eventAt.getTime() - event.changeCutoffHours * 3_600_000)
+        : new Date(Date.now() + 48 * 3_600_000)
+
+      let sent = 0
+      for (const am of ams) {
+        if (!am.user.email) continue
+        try {
+          await sendLunchReminderEmail({
+            to: am.user.email,
+            memberName: am.user.name ?? am.user.email,
+            eventAt: event.eventAt ?? new Date(),
+            venue: event.venue,
+            changeDeadline: deadline,
+            pickUrl: `${process.env.NEXTAUTH_URL ?? ''}/applicant`,
+          })
+          sent++
+        } catch (e) {
+          console.error('[lunch.sendReminders] send failed for', am.user.email, e)
+        }
+      }
+      return { sent }
+    }),
+
   /** Patch any subset of LunchEvent config fields. Audit-logged. */
   updateEvent: adminProcedure
     .input(

src/server/services/lunch-reminders.ts

@@ -0,0 +1,32 @@
+import type { PrismaClient } from '@prisma/client'
+
+/**
+ * Return all AttendingMember rows (with user) that:
+ *  - belong to a CONFIRMED FinalistConfirmation in the given program
+ *  - have NOT yet picked a lunch dish (no MemberLunchPick row OR pick row with pickedAt=null)
+ *
+ * This is extracted from the cron so it can be unit-tested independently and
+ * reused by the manual `sendReminders` admin action.
+ *
+ * Bug context: Prisma `lunchPick: { is: { pickedAt: null } }` only matches rows
+ * that EXIST but have pickedAt=null.  Attendees with no pick row at all fall
+ * through.  The correct filter is the OR form below.
+ */
+export async function selectUnpickedAttendees(
+  prisma: PrismaClient,
+  event: { id: string; programId: string },
+) {
+  return prisma.attendingMember.findMany({
+    where: {
+      confirmation: {
+        project: { programId: event.programId },
+        status: 'CONFIRMED',
+      },
+      OR: [
+        { lunchPick: { is: null } },
+        { lunchPick: { is: { pickedAt: null } } },
+      ],
+    },
+    include: { user: { select: { name: true, email: true } } },
+  })
+}

tests/unit/lunch-reminder-filter.test.ts

@@ -0,0 +1,140 @@
+/**
+ * Regression: selectUnpickedAttendees must return attendees with NO MemberLunchPick
+ * row at all, not just attendees whose pick row has pickedAt=null.
+ *
+ * Bug: the old cron filter used `lunchPick: { is: { pickedAt: null } }` which
+ * only matches rows that exist but have pickedAt=null.  Attendees with no pick
+ * row at all were silently skipped.
+ */
+import { afterAll, describe, expect, it } from 'vitest'
+import { prisma } from '../setup'
+import {
+  createTestUser,
+  createTestProgram,
+  createTestProject,
+  cleanupTestData,
+  uid,
+} from '../helpers'
+import { selectUnpickedAttendees } from '@/server/services/lunch-reminders'
+
+const programIds: string[] = []
+const userIds: string[] = []
+
+afterAll(async () => {
+  for (const programId of programIds) {
+    await prisma.memberLunchPick.deleteMany({
+      where: { attendingMember: { confirmation: { project: { programId } } } },
+    })
+    await prisma.attendingMember.deleteMany({
+      where: { confirmation: { project: { programId } } },
+    })
+    await prisma.finalistConfirmation.deleteMany({ where: { project: { programId } } })
+    await prisma.lunchEvent.deleteMany({ where: { programId } })
+    await cleanupTestData(programId, [])
+  }
+  if (userIds.length > 0) {
+    await prisma.auditLog.deleteMany({ where: { userId: { in: userIds } } })
+    await prisma.user.deleteMany({ where: { id: { in: userIds } } })
+  }
+})
+
+describe('selectUnpickedAttendees', () => {
+  it('returns attendees with no pick row AND unpicked rows; excludes picked', async () => {
+    const program = await createTestProgram({ name: `rfilter-${uid()}` })
+    programIds.push(program.id)
+
+    // Three confirmed attendees on the same program
+    const u1 = await createTestUser('APPLICANT') // no MemberLunchPick row at all
+    const u2 = await createTestUser('APPLICANT') // MemberLunchPick with pickedAt=null
+    const u3 = await createTestUser('APPLICANT') // MemberLunchPick with pickedAt set (PICKED)
+    userIds.push(u1.id, u2.id, u3.id)
+
+    const project = await createTestProject(program.id, {
+      title: `rfilter-proj-${uid()}`,
+      competitionCategory: 'STARTUP',
+    })
+
+    const conf = await prisma.finalistConfirmation.create({
+      data: {
+        projectId: project.id,
+        category: 'STARTUP',
+        status: 'CONFIRMED',
+        deadline: new Date(Date.now() + 86_400_000),
+        token: `tok-${uid()}`,
+      },
+    })
+
+    const am1 = await prisma.attendingMember.create({
+      data: { confirmationId: conf.id, userId: u1.id },
+    })
+    const am2 = await prisma.attendingMember.create({
+      data: { confirmationId: conf.id, userId: u2.id },
+    })
+    const am3 = await prisma.attendingMember.create({
+      data: { confirmationId: conf.id, userId: u3.id },
+    })
+
+    // am1: NO pick row
+    // am2: pick row exists but pickedAt=null
+    await prisma.memberLunchPick.create({
+      data: { attendingMemberId: am2.id },
+    })
+    // am3: pick row with pickedAt set (has picked)
+    await prisma.memberLunchPick.create({
+      data: { attendingMemberId: am3.id, pickedAt: new Date() },
+    })
+
+    const event = await prisma.lunchEvent.create({
+      data: { programId: program.id, enabled: true },
+    })
+
+    const result = await selectUnpickedAttendees(prisma, {
+      id: event.id,
+      programId: program.id,
+    })
+
+    const returnedIds = result.map((am) => am.id).sort()
+    expect(returnedIds).toContain(am1.id)
+    expect(returnedIds).toContain(am2.id)
+    expect(returnedIds).not.toContain(am3.id)
+    expect(result).toHaveLength(2)
+  })
+
+  it('excludes non-CONFIRMED confirmations', async () => {
+    const program = await createTestProgram({ name: `rfilter-nc-${uid()}` })
+    programIds.push(program.id)
+
+    const u = await createTestUser('APPLICANT')
+    userIds.push(u.id)
+
+    const project = await createTestProject(program.id, {
+      title: `rfilter-nc-${uid()}`,
+      competitionCategory: 'STARTUP',
+    })
+
+    const conf = await prisma.finalistConfirmation.create({
+      data: {
+        projectId: project.id,
+        category: 'STARTUP',
+        status: 'PENDING', // NOT confirmed
+        deadline: new Date(Date.now() + 86_400_000),
+        token: `tok-${uid()}`,
+      },
+    })
+
+    await prisma.attendingMember.create({
+      data: { confirmationId: conf.id, userId: u.id },
+    })
+
+    const event = await prisma.lunchEvent.create({
+      data: { programId: program.id, enabled: true },
+    })
+
+    const result = await selectUnpickedAttendees(prisma, {
+      id: event.id,
+      programId: program.id,
+    })
+
+    expect(result).toHaveLength(0)
+  })
+})