Merge: mentorship comms + welcome/reminder email

- Email-all-team-members button for mentors
- Upgraded round-open emails (instructions + contact addresses)
- Admin re-sendable welcome/reminder blast with live preview
- New tRPC: mentor.previewMentorshipWelcome / sendMentorshipWelcome

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

docs/superpowers/specs/2026-06-01-mentorship-comms-and-welcome-email-design.md

@@ -0,0 +1,122 @@
+# Mentorship Communications & Welcome/Reminder Email — Design
+
+- **Date:** 2026-06-01
+- **Status:** Approved (pending spec review)
+- **Author:** Matt + Claude
+- **Topic:** Make mentor↔team contact effortless and add a re-sendable, instructional "welcome/reminder" email for mentoring rounds.
+
+## Context
+
+MOPC already has a working mentorship feature:
+
+- **Two-way in-app messaging** exists (`MentorMessage` model; `WorkspaceChat` + `MentorChat` components; `trpc.mentor.sendMessage` / `getMessages` and `trpc.applicant.sendMentorMessage` / `getMentorMessages`). Mentors are auto-notified when applicants write.
+- **Contact emails are already visible**: mentors see each team member's email as individual `mailto:` links (`src/app/(mentor)/mentor/projects/[id]/page.tsx`); applicants see their mentor's name+email (`src/app/(applicant)/applicant/mentor/page.tsx`) and teammates' emails (`src/app/(applicant)/applicant/team/page.tsx`).
+- **Round-open auto emails already fire**: flipping a `MENTORING` round draft→active sends a coalesced *"you've been assigned to N projects"* email to each mentor (`getMentorBulkAssignmentTemplate` / `sendMentorBulkAssignmentEmail`) and a *"meet your mentors"* intro to each team (`getTeamMentorIntroductionTemplate` / `sendTeamMentorIntroductionEmail`). These are one-time, gated by `MentorAssignment.notificationSentAt` and `MentorAssignment.teamIntroducedAt` (`src/server/services/round-engine.ts`).
+
+Two gaps remain:
+
+1. There is **no single "email all team members"** affordance for mentors — only per-person `mailto:` links.
+2. The round-open emails **don't explain how to use the mentorship features**, and there is **no way to re-send** them later as a reminder.
+
+## Goals
+
+- A mentor can email their whole team in one click (opens their mail client, all members in `To:`).
+- The round-open assignment emails are **upgraded in place** to include (a) the relevant contact emails and (b) how-to-use-the-mentorship-features instructions.
+- An admin can **re-send** that same email on demand (a "welcome/reminder" blast) to all mentors + teams in a mentoring round, with an optional custom note.
+- The admin can **preview** the exact email (mentor + team versions) before sending.
+
+## Non-goals
+
+- No new in-app messaging surfaces (the chat already exists).
+- No new email-provider infrastructure (reuse `src/lib/email.ts` wrapper, helpers, throttling, `NotificationLog`).
+- No mentors-only / teams-only targeting toggle for v1 — the reminder sends to **both** audiences. (Can be added later if needed.)
+
+## Feature 1 — Mentor "Email all team members" button
+
+- **Location:** `src/app/(mentor)/mentor/projects/[id]/page.tsx`, in the existing Team Members card, alongside the per-member `mailto:` links.
+- **Behavior:** builds `mailto:<comma-joined emails>?subject=...` with **all active team members in `To:`** (per decision), subject pre-filled `MOPC Mentorship — {project title}`. Clicking opens the mentor's default mail app.
+- **Edge cases:** filter out blank/missing emails defensively (schema makes `User.email` required+non-null, but be safe); hide the button when the team has zero emailable members.
+- **Scope:** pure client-side; no backend changes.
+
+## Feature 2 — Unified mentorship welcome/reminder email
+
+### Decision: upgrade in place, don't duplicate
+
+Rather than send a second email on round-open, the **existing** two templates are enhanced so they carry the instructions + contact emails. The same template code is reused by both trigger paths below. One email per audience; one source of truth.
+
+### Content — Mentor version (coalesced per mentor, across their projects in the round)
+
+- Greeting by mentor name.
+- Optional custom note (rendered in an info box near the top) — only present on the manual reminder path.
+- For **each** assigned project: project title (linked) + the **team members listed with name + email**.
+- "How to mentor on MOPC" instructions block: where the workspace chat lives, file sharing, the mentor dashboard.
+- CTA → Mentor Dashboard.
+
+### Content — Team version (per project)
+
+- Greeting by recipient name.
+- Optional custom note (info box) — manual path only.
+- The assigned **mentor(s) listed with name + email**.
+- The team's **own members listed with email** (per decision: include teammates too).
+- "How to work with your mentor" instructions block: where the in-app chat is, how to reach the mentor, what to expect.
+- CTA → mentoring page.
+
+Both reuse `getEmailWrapper()` and existing helpers (`sectionTitle`, `paragraph`, `ctaButton`, `infoBox`, `escapeHtml`) for consistent branding.
+
+### Trigger path A — auto on round-open (existing flow, upgraded content)
+
+- `src/server/services/round-engine.ts` draft→active flow keeps its one-time semantics (`notificationSentAt` / `teamIntroducedAt` gating) and coalescing.
+- It now passes the additional data the upgraded templates need: team-member name+email for the mentor email, and mentor name+email + teammate emails for the team email.
+- No custom note on this path.
+
+### Trigger path B — manual reminder button (admin, on demand)
+
+- New `adminProcedure`: `mentor.sendMentorshipWelcome({ roundId, customNote?: string })`.
+  - Resolves **all current** active assignments for the round (`droppedAt: null`) → groups by mentor → sends mentor emails; resolves all projects with assignments → sends team emails to all members.
+  - **Ignores** `notificationSentAt` / `teamIntroducedAt` (deliberate re-send). Does **not** mutate those flags.
+  - Throttled + fire-and-forget like existing bulk sends; writes `NotificationLog` rows + a `DecisionAuditLog`/audit entry.
+  - Returns counts: `{ mentorCount, teamMemberCount, teamCount }` for the success toast.
+
+### Preview
+
+- New query: `mentor.previewMentorshipWelcome({ roundId, customNote?: string })` → `{ mentor: { subject, html }, team: { subject, html } }`.
+  - Calls the **same** template functions used by the real send.
+  - Picks a representative recipient: first mentor with assignments + first project/team in the round. If the round has none yet, returns clearly-labeled sample-data output so the layout is still previewable.
+- Rendered in the send dialog inside a sandboxed `<iframe srcDoc={html}>` (isolates email CSS from the app), with **Mentor / Team** sub-tabs. The custom-note textarea updates the preview live (debounced).
+
+### Admin UI
+
+- New component `src/components/admin/round/send-mentorship-welcome-button.tsx`:
+  - Lives in the round detail page's **Notifications** section (`src/app/(admin)/admin/rounds/[roundId]/page.tsx`, near `NotifyAdvancedButton` / `NotifyRejectedButton` / `BulkInviteButton`), rendered **only when the round is `MENTORING`**.
+  - Opens a dialog: recipient summary ("N mentors · M team members across K teams"), optional custom-note textarea, live Preview (Mentor/Team tabs), and a Send button with confirmation.
+
+## Files touched
+
+| File | Change |
+|---|---|
+| `src/app/(mentor)/mentor/projects/[id]/page.tsx` | Add "Email all team members" button (mailto, all in To:) |
+| `src/lib/email.ts` | Enhance `getMentorBulkAssignmentTemplate` + `getTeamMentorIntroductionTemplate` (contacts, instructions, optional `customNote`); update `sendMentorBulkAssignmentEmail` / `sendTeamMentorIntroductionEmail` signatures + all call sites |
+| `src/server/services/round-engine.ts` | Pass team-member/mentor emails into upgraded templates on round-open |
+| `src/server/routers/mentor.ts` | New `sendMentorshipWelcome` (adminProcedure) + `previewMentorshipWelcome` (adminProcedure query) |
+| `src/components/admin/round/send-mentorship-welcome-button.tsx` (new) | Dialog: counts, custom note, live iframe preview, send |
+| `src/app/(admin)/admin/rounds/[roundId]/page.tsx` | Wire the button into the Notifications section, gated to mentoring rounds |
+
+## Implementation ordering note
+
+Build the templates first and render both to standalone `.html` files (and/or screenshots) for copy review **before** wiring the send path — gives an early visual check with zero throwaway work.
+
+## Testing
+
+- **Template unit tests** (`src/lib/email.ts` fns return `{ subject, html, text }`, easy to assert): mentor email contains each team member's email + instructions block; team email contains mentor email(s) + teammate emails + instructions; custom note appears when passed, absent when not.
+- **tRPC test** for `sendMentorshipWelcome` on a seeded mentoring round: correct recipient resolution and returned counts; does not flip the one-time flags.
+- **tRPC test** for `previewMentorshipWelcome`: returns non-empty mentor + team HTML for a seeded round; sample-data fallback for an empty round.
+
+## Decisions (resolved during brainstorming)
+
+1. Upgrade existing intro emails in place (single source of truth), reused by both auto-open and the manual reminder; fallback would have been a standalone manual-only blast.
+2. Tailored content per audience (mentor vs team), **with contact emails embedded** in the relevant spot.
+3. Manual reminder: fixed branded template **+ optional custom note**.
+4. "Email all" button: **all members in `To:`**.
+5. Team email includes **both** the mentor's email and teammates' emails.
+6. Manual reminder sends to **both** audiences (no per-audience toggle in v1).
+7. Preview via an in-app button (live, real-data, iframe) rather than pasted static HTML.

src/app/(admin)/admin/rounds/[roundId]/page.tsx

@@ -125,6 +125,7 @@ import { ConfigSectionHeader } from '@/components/admin/rounds/config/config-sec
 import { NotifyAdvancedButton } from '@/components/admin/round/notify-advanced-button'
 import { NotifyRejectedButton } from '@/components/admin/round/notify-rejected-button'
 import { BulkInviteButton } from '@/components/admin/round/bulk-invite-button'
+import { SendMentorshipWelcomeButton } from '@/components/admin/round/send-mentorship-welcome-button'
 import { AdvancementSummaryCard } from '@/components/admin/round/advancement-summary-card'
 import { FinalizationTab } from '@/components/admin/round/finalization-tab'
 
@@ -1442,6 +1443,7 @@ export default function RoundDetailPage() {
                       <NotifyAdvancedButton roundId={roundId} />
                       <NotifyRejectedButton roundId={roundId} />
                       <BulkInviteButton roundId={roundId} />
+                      {isMentoring && <SendMentorshipWelcomeButton roundId={roundId} />}
                     </div>
                   </div>
                 )}

src/app/(mentor)/mentor/projects/[id]/page.tsx

@@ -344,6 +344,25 @@ function ProjectDetailContent({ projectId }: { projectId: string }) {
           </CardDescription>
         </CardHeader>
         <CardContent className="space-y-4">
+            {(() => {
+              const emails = (project.teamMembers ?? [])
+                .map((m) => m.user.email)
+                .filter((e): e is string => !!e)
+              if (emails.length === 0) return null
+              const mailto = `mailto:${emails.join(',')}?subject=${encodeURIComponent(
+                `MOPC Mentorship — ${project.title}`,
+              )}`
+              return (
+                <div className="flex justify-end">
+                  <Button variant="outline" size="sm" asChild>
+                    <a href={mailto}>
+                      <Mail className="mr-2 h-4 w-4" />
+                      Email all team members
+                    </a>
+                  </Button>
+                </div>
+              )
+            })()}
           {/* Team Lead */}
           {teamLead && (
             <div className="p-4 rounded-lg border bg-muted/30">

src/components/admin/round/send-mentorship-welcome-button.tsx

@@ -0,0 +1,61 @@
+'use client'
+
+import { useState } from 'react'
+import { trpc } from '@/lib/trpc/client'
+import { toast } from 'sonner'
+import { Mail } from 'lucide-react'
+import { EmailPreviewDialog } from './email-preview-dialog'
+
+interface SendMentorshipWelcomeButtonProps {
+  roundId: string
+}
+
+export function SendMentorshipWelcomeButton({ roundId }: SendMentorshipWelcomeButtonProps) {
+  const [open, setOpen] = useState(false)
+  const [customMessage, setCustomMessage] = useState<string | undefined>()
+
+  const preview = trpc.mentor.previewMentorshipWelcome.useQuery(
+    { roundId, customNote: customMessage },
+    { enabled: open },
+  )
+
+  const sendMutation = trpc.mentor.sendMentorshipWelcome.useMutation({
+    onSuccess: (data) => {
+      toast.success(
+        `Sent ${data.sent} email${data.sent !== 1 ? 's' : ''}${data.failed ? ` (${data.failed} failed)` : ''}`,
+      )
+      setOpen(false)
+    },
+    onError: (err) => toast.error(err.message),
+  })
+
+  return (
+    <>
+      <button
+        onClick={() => setOpen(true)}
+        className="flex items-start gap-3 p-4 rounded-lg border border-l-4 border-l-sky-500 hover:-translate-y-0.5 hover:shadow-md transition-all text-left w-full"
+      >
+        <Mail className="h-5 w-5 text-sky-600 mt-0.5 shrink-0" />
+        <div>
+          <p className="text-sm font-medium">Send Welcome / Reminder</p>
+          <p className="text-xs text-muted-foreground mt-0.5">
+            Email all mentors &amp; teams how to use mentorship
+          </p>
+        </div>
+      </button>
+
+      <EmailPreviewDialog
+        open={open}
+        onOpenChange={setOpen}
+        title="Send Mentorship Welcome / Reminder"
+        description="Emails every mentor and team member in this round with their assignment and how to use the mentorship features. You can add an optional note below."
+        recipientCount={preview.data?.recipientCount ?? 0}
+        previewHtml={preview.data?.html}
+        isPreviewLoading={preview.isLoading}
+        onSend={(msg) => sendMutation.mutate({ roundId, customNote: msg })}
+        isSending={sendMutation.isPending}
+        onRefreshPreview={(msg) => setCustomMessage(msg)}
+      />
+    </>
+  )
+}

src/lib/email.ts

@@ -2832,11 +2832,13 @@ export async function sendMentorTeamAssignmentEmail(
   }
 }
 
-function getTeamMentorIntroductionTemplate(
+export function getTeamMentorIntroductionTemplate(
   recipientName: string | null,
   projectTitle: string,
   mentors: { name: string | null; email: string }[],
   workspaceUrl: string,
+  teammates?: { name: string | null; email: string }[],
+  customNote?: string,
 ): EmailTemplate {
   const count = mentors.length
   const subject =
@@ -2846,40 +2848,73 @@ function getTeamMentorIntroductionTemplate(
   const greeting = recipientName ? `Hi ${recipientName},` : 'Hi there,'
 
   const mentorTextLines = mentors
-    .map(
+    .map((m) => `  • ${m.name ?? 'Mentor'} — ${m.email}`)
-      (m) => `  • ${m.name ?? 'Mentor'} — ${m.email}`,
-    )
     .join('\n')
+  const teammateTextLines =
+    teammates && teammates.length > 0
+      ? ['', 'Your team:', ...teammates.map((t) => `  • ${t.name ?? 'Team member'} — ${t.email}`)]
+      : []
 
   const text = [
     greeting,
     '',
+    ...(customNote ? [customNote, ''] : []),
     count === 1
       ? `The mentoring round is now open, and your project "${projectTitle}" has a mentor:`
       : `The mentoring round is now open, and your project "${projectTitle}" has ${count} mentors:`,
     '',
     mentorTextLines,
+    ...teammateTextLines,
     '',
-    'You can chat with them, share files, and track milestones in your mentor workspace:',
+    'Working with your mentor:',
-    workspaceUrl,
+    '  - Go to the Mentoring section of your applicant portal to message your mentor directly — they are notified by email when you write.',
+    '  - Share documents and questions early; your mentor is here to help you sharpen your project before the finals.',
+    '  - You can also email your mentor directly using the address above.',
     '',
-    'Feel free to reach out to them directly by email as well.',
+    `Open your mentoring page: ${workspaceUrl}`,
     '',
     'The MOPC team',
   ].join('\n')
 
+  const customNoteHtml = customNote
+    ? `<div style="margin:0 0 16px;padding:12px 16px;background:#fff7ed;border-left:3px solid #de0f1e;border-radius:4px;color:#0f172a;">${escapeHtml(customNote)}</div>`
+    : ''
+
   const mentorHtmlList = mentors
     .map(
       (m) => `
         <tr>
           <td style="padding:6px 0;font-weight:600;color:#0f172a;">${escapeHtml(m.name ?? 'Mentor')}</td>
-          <td style="padding:6px 0;">
+          <td style="padding:6px 0;"><a href="mailto:${escapeHtml(m.email)}" style="color:#053d57;text-decoration:none;">${escapeHtml(m.email)}</a></td>
-            <a href="mailto:${escapeHtml(m.email)}" style="color:#053d57;text-decoration:none;">${escapeHtml(m.email)}</a>
-          </td>
         </tr>`,
     )
     .join('')
 
+  const teammatesHtml =
+    teammates && teammates.length > 0
+      ? `
+      <h2 style="margin:24px 0 8px;color:#0f172a;font-size:15px;font-weight:600;">Your team</h2>
+      <table style="width:100%;border-collapse:collapse;margin:0 0 8px;font-size:14px;">${teammates
+        .map(
+          (t) => `
+        <tr>
+          <td style="padding:6px 0;color:#0f172a;">${escapeHtml(t.name ?? 'Team member')}</td>
+          <td style="padding:6px 0;"><a href="mailto:${escapeHtml(t.email)}" style="color:#053d57;text-decoration:none;">${escapeHtml(t.email)}</a></td>
+        </tr>`,
+        )
+        .join('')}</table>`
+      : ''
+
+  const instructionsHtml = `
+    <div style="margin:16px 0;padding:12px 16px;background:#eff6ff;border-left:3px solid #3b82f6;border-radius:4px;">
+      <strong style="color:#1e40af;">Working with your mentor</strong>
+      <ul style="margin:8px 0 0 20px;padding:0;color:#0f172a;font-size:13px;">
+        <li style="margin:4px 0;">Go to the Mentoring section of your applicant portal to message your mentor directly — they are notified by email when you write.</li>
+        <li style="margin:4px 0;">Share documents and questions early; your mentor is here to help you sharpen your project before the finals.</li>
+        <li style="margin:4px 0;">You can also email your mentor directly using the address above.</li>
+      </ul>
+    </div>`
+
   const html = `
 <!DOCTYPE html>
 <html>
@@ -2890,16 +2925,16 @@ function getTeamMentorIntroductionTemplate(
     </div>
     <div style="padding:24px 28px;line-height:1.5;font-size:14px;">
       <p style="margin-top:0;">${recipientName ? `Hi ${escapeHtml(recipientName)},` : 'Hi there,'}</p>
+      ${customNoteHtml}
       <p>${count === 1
         ? `The mentoring round is now open and a mentor has been assigned to your project <strong>${escapeHtml(projectTitle)}</strong>:`
         : `The mentoring round is now open and <strong>${count}</strong> mentors have been assigned to your project <strong>${escapeHtml(projectTitle)}</strong>:`}</p>
-      <table style="width:100%;border-collapse:collapse;margin:12px 0 20px;font-size:14px;">${mentorHtmlList}</table>
+      <table style="width:100%;border-collapse:collapse;margin:12px 0 8px;font-size:14px;">${mentorHtmlList}</table>
+      ${teammatesHtml}
+      ${instructionsHtml}
       <p style="margin-top:24px;">
         <a href="${workspaceUrl}" style="display:inline-block;padding:10px 20px;background:#de0f1e;color:#fff;text-decoration:none;border-radius:6px;font-weight:600;">Open Mentor Workspace</a>
       </p>
-      <p style="margin-top:24px;color:#64748b;font-size:12px;">
-        You can chat with them, share files, and track milestones in the workspace — or reach out to them directly by email.
-      </p>
     </div>
     <div style="padding:16px 28px;background:#f1f5f9;color:#64748b;font-size:12px;text-align:center;">
       Monaco Ocean Protection Challenge
@@ -2924,16 +2959,20 @@ export async function sendTeamMentorIntroductionEmail(
   projectTitle: string,
   projectId: string,
   mentors: { name: string | null; email: string }[],
-): Promise<void> {
+  teammates?: { name: string | null; email: string }[],
+  customNote?: string,
+): Promise<boolean> {
   try {
-    if (mentors.length === 0) return
+    if (mentors.length === 0) return false
-    const baseUrl = (process.env.NEXTAUTH_URL || 'https://monaco-opc.com').replace(/\/$/, '')
+    const baseUrl = getBaseUrl()
     const workspaceUrl = `${baseUrl}/applicant/mentor`
     const template = getTeamMentorIntroductionTemplate(
       recipientName,
       projectTitle,
       mentors,
       workspaceUrl,
+      teammates,
+      customNote,
     )
     await sendEmail({
       to: recipientEmail,
@@ -2941,15 +2980,22 @@ export async function sendTeamMentorIntroductionEmail(
       text: template.text,
       html: template.html,
     })
+    return true
   } catch (error) {
     console.error('[sendTeamMentorIntroductionEmail] failed', { recipientEmail, projectId, error })
+    return false
   }
 }
 
-function getMentorBulkAssignmentTemplate(
+export function getMentorBulkAssignmentTemplate(
   name: string,
-  projects: { title: string; url: string }[],
+  projects: {
+    title: string
+    url: string
+    teamMembers?: { name: string | null; email: string }[]
+  }[],
   mentorDashboardUrl: string,
+  customNote?: string,
 ): EmailTemplate {
   const count = projects.length
   const subject =
@@ -2958,32 +3004,65 @@ function getMentorBulkAssignmentTemplate(
       : `You've been assigned to ${count} new MOPC projects`
   const greeting = name ? `Hi ${name},` : 'Hi there,'
 
-  const textLines = projects
+  const textBlocks = projects.map((p) => {
-    .map((p) => `  • ${p.title} — ${p.url}`)
+    const members =
+      p.teamMembers && p.teamMembers.length > 0
+        ? '\n' +
+          p.teamMembers
+            .map((m) => `      - ${m.name ?? 'Team member'}: ${m.email}`)
             .join('\n')
+        : ''
+    return `  • ${p.title} — ${p.url}${members}`
+  })
   const text = [
     greeting,
     '',
+    ...(customNote ? [customNote, ''] : []),
     count === 1
       ? `You have been assigned as a mentor to a new project:`
       : `You have been assigned as a mentor to ${count} new projects:`,
     '',
-    textLines,
+    ...textBlocks,
     '',
-    'You may have co-mentors on these teams — you can collaborate together in each project workspace.',
+    'How to mentor on MOPC:',
+    '  - Open each project workspace from your Mentor Dashboard to chat with the team, share files, and track milestones.',
+    '  - Messages you send in the workspace notify the team by email automatically.',
+    '  - You can also email team members directly using the addresses listed above.',
     '',
     `Open your mentor dashboard: ${mentorDashboardUrl}`,
     '',
     'The MOPC team',
   ].join('\n')
 
+  const customNoteHtml = customNote
+    ? `<div style="margin:0 0 16px;padding:12px 16px;background:#fff7ed;border-left:3px solid #de0f1e;border-radius:4px;color:#0f172a;">${escapeHtml(customNote)}</div>`
+    : ''
+
   const htmlList = projects
+    .map((p) => {
+      const members =
+        p.teamMembers && p.teamMembers.length > 0
+          ? `<table style="width:100%;border-collapse:collapse;margin:6px 0 0;font-size:13px;">${p.teamMembers
               .map(
-      (p) =>
+                (m) =>
-        `<li style="margin:6px 0;"><a href="${p.url}" style="color:#053d57;text-decoration:none;font-weight:600;">${escapeHtml(p.title)}</a></li>`,
+                  `<tr><td style="padding:3px 0;color:#0f172a;">${escapeHtml(m.name ?? 'Team member')}</td><td style="padding:3px 0;"><a href="mailto:${escapeHtml(m.email)}" style="color:#053d57;text-decoration:none;">${escapeHtml(m.email)}</a></td></tr>`,
               )
+              .join('')}</table>`
+          : ''
+      return `<li style="margin:10px 0;"><a href="${p.url}" style="color:#053d57;text-decoration:none;font-weight:600;">${escapeHtml(p.title)}</a>${members}</li>`
+    })
     .join('')
 
+  const instructionsHtml = `
+    <div style="margin:16px 0;padding:12px 16px;background:#eff6ff;border-left:3px solid #3b82f6;border-radius:4px;">
+      <strong style="color:#1e40af;">How to mentor on MOPC</strong>
+      <ul style="margin:8px 0 0 20px;padding:0;color:#0f172a;font-size:13px;">
+        <li style="margin:4px 0;">Open each project workspace from your Mentor Dashboard to chat with the team, share files, and track milestones.</li>
+        <li style="margin:4px 0;">Messages you send in the workspace notify the team by email automatically.</li>
+        <li style="margin:4px 0;">You can also email team members directly using the addresses listed above.</li>
+      </ul>
+    </div>`
+
   const html = `
 <!DOCTYPE html>
 <html>
@@ -2994,14 +3073,13 @@ function getMentorBulkAssignmentTemplate(
     </div>
     <div style="padding:24px 28px;line-height:1.5;font-size:14px;">
       <p style="margin-top:0;">${name ? `Hi ${escapeHtml(name)},` : 'Hi there,'}</p>
+      ${customNoteHtml}
       <p>${count === 1 ? 'You have been assigned as a mentor to a new project:' : `You have been assigned as a mentor to <strong>${count}</strong> new projects:`}</p>
       <ul style="padding-left:20px;margin:12px 0 20px;">${htmlList}</ul>
+      ${instructionsHtml}
       <p style="margin-top:24px;">
         <a href="${mentorDashboardUrl}" style="display:inline-block;padding:10px 20px;background:#de0f1e;color:#fff;text-decoration:none;border-radius:6px;font-weight:600;">Open Mentor Dashboard</a>
       </p>
-      <p style="margin-top:24px;color:#64748b;font-size:12px;">
-        You may have co-mentors on these teams — you can collaborate together in each project workspace.
-      </p>
     </div>
     <div style="padding:16px 28px;background:#f1f5f9;color:#64748b;font-size:12px;text-align:center;">
       Monaco Ocean Protection Challenge
@@ -3023,23 +3101,23 @@ function getMentorBulkAssignmentTemplate(
 export async function sendMentorBulkAssignmentEmail(
   email: string,
   name: string | null,
-  projects: { id: string; title: string }[],
+  projects: { id: string; title: string; teamMembers?: { name: string | null; email: string }[] }[],
-): Promise<void> {
+  customNote?: string,
+): Promise<boolean> {
   try {
-    if (projects.length === 0) return
+    if (projects.length === 0) return false
-    const baseUrl = (process.env.NEXTAUTH_URL || 'https://monaco-opc.com').replace(/\/$/, '')
+    const baseUrl = getBaseUrl()
     const enriched = projects.map((p) => ({
       title: p.title,
       url: `${baseUrl}/mentor/workspace/${p.id}`,
+      teamMembers: p.teamMembers,
     }))
-    const template = getMentorBulkAssignmentTemplate(
+    const template = getMentorBulkAssignmentTemplate(name || '', enriched, `${baseUrl}/mentor`, customNote)
-      name || '',
-      enriched,
-      `${baseUrl}/mentor`,
-    )
     await sendEmail({ to: email, subject: template.subject, text: template.text, html: template.html })
+    return true
   } catch (error) {
     console.error('[sendMentorBulkAssignmentEmail] failed', { email, error })
+    return false
   }
 }
 

src/server/routers/mentor.ts

@@ -12,6 +12,9 @@ import {
   sendMentorChangeRequestEmail,
   sendMentorTeamAssignmentEmail,
   sendTeamMentorIntroductionEmail,
+  getMentorBulkAssignmentTemplate,
+  getTeamMentorIntroductionTemplate,
+  getBaseUrl,
 } from '@/lib/email'
 import {
   getAIMentorSuggestions,
@@ -3287,4 +3290,208 @@ export const mentorRouter = router({
 
       return updated
     }),
+
+  previewMentorshipWelcome: adminProcedure
+    .input(z.object({ roundId: z.string(), customNote: z.string().max(2000).optional() }))
+    .query(async ({ ctx, input }) => {
+      const { roundId, customNote } = input
+      const baseUrl = getBaseUrl()
+
+      const assignments = await ctx.prisma.mentorAssignment.findMany({
+        where: { droppedAt: null, project: { projectRoundStates: { some: { roundId } } } },
+        select: {
+          mentorId: true,
+          mentor: { select: { name: true, email: true } },
+          project: {
+            select: {
+              id: true,
+              title: true,
+              teamMembers: { select: { user: { select: { name: true, email: true } } } },
+            },
+          },
+        },
+      })
+
+      const mentorIds = new Set<string>()
+      const teamEmails = new Set<string>()
+      for (const a of assignments) {
+        if (a.mentor?.email) mentorIds.add(a.mentorId)
+        for (const tm of a.project.teamMembers) {
+          if (tm.user?.email) teamEmails.add(tm.user.email)
+        }
+      }
+      const recipientCount = mentorIds.size + teamEmails.size
+
+      const firstMentor = assignments.find((a) => a.mentor?.email)
+      const mentorTemplate = firstMentor
+        ? getMentorBulkAssignmentTemplate(
+            firstMentor.mentor!.name || '',
+            assignments
+              .filter((a) => a.mentorId === firstMentor.mentorId)
+              .map((a) => ({
+                title: a.project.title,
+                url: `${baseUrl}/mentor/workspace/${a.project.id}`,
+                teamMembers: a.project.teamMembers
+                  .filter((tm) => tm.user?.email)
+                  .map((tm) => ({ name: tm.user!.name, email: tm.user!.email })),
+              })),
+            `${baseUrl}/mentor`,
+            customNote,
+          )
+        : getMentorBulkAssignmentTemplate(
+            'Sample Mentor',
+            [
+              {
+                title: 'Sample Project',
+                url: `${baseUrl}/mentor`,
+                teamMembers: [{ name: 'Sample Applicant', email: 'applicant@example.com' }],
+              },
+            ],
+            `${baseUrl}/mentor`,
+            customNote,
+          )
+
+      const firstProject = assignments.find((a) => a.mentor?.email)
+      let teamTemplate
+      if (firstProject) {
+        const projMentors = assignments
+          .filter((a) => a.project.id === firstProject.project.id && a.mentor?.email)
+          .map((a) => ({ name: a.mentor!.name, email: a.mentor!.email }))
+        const teammates = firstProject.project.teamMembers
+          .filter((tm) => tm.user?.email)
+          .map((tm) => ({ name: tm.user!.name, email: tm.user!.email }))
+        teamTemplate = getTeamMentorIntroductionTemplate(
+          teammates[0]?.name ?? null,
+          firstProject.project.title,
+          projMentors,
+          `${baseUrl}/applicant/mentor`,
+          teammates.slice(1),
+          customNote,
+        )
+      } else {
+        teamTemplate = getTeamMentorIntroductionTemplate(
+          'Sample Applicant',
+          'Sample Project',
+          [{ name: 'Sample Mentor', email: 'mentor@example.com' }],
+          `${baseUrl}/applicant/mentor`,
+          [{ name: 'Sample Teammate', email: 'teammate@example.com' }],
+          customNote,
+        )
+      }
+
+      const isSample = !firstMentor
+      const banner = (label: string) =>
+        `<div style="max-width:560px;margin:24px auto 0;padding:10px 14px;background:#053d57;color:#fff;font-weight:600;text-align:center;border-radius:6px;font-family:-apple-system,sans-serif;">${label}</div>`
+      const sampleNote = isSample
+        ? `<div style="max-width:560px;margin:16px auto 0;padding:10px 14px;background:#fff7ed;color:#9a3412;text-align:center;border-radius:6px;font-family:-apple-system,sans-serif;">No assignments in this round yet — showing sample data.</div>`
+        : ''
+
+      const html = `${sampleNote}${banner('Mentor version')}${mentorTemplate.html}${banner('Team version')}${teamTemplate.html}`
+
+      return { html, recipientCount }
+    }),
+
+  sendMentorshipWelcome: adminProcedure
+    .input(z.object({ roundId: z.string(), customNote: z.string().max(2000).optional() }))
+    .mutation(async ({ ctx, input }) => {
+      const { roundId, customNote } = input
+
+      const assignments = await ctx.prisma.mentorAssignment.findMany({
+        where: { droppedAt: null, project: { projectRoundStates: { some: { roundId } } } },
+        select: {
+          id: true,
+          mentorId: true,
+          mentor: { select: { name: true, email: true } },
+          project: {
+            select: {
+              id: true,
+              title: true,
+              teamMembers: { select: { user: { select: { name: true, email: true } } } },
+              submittedByEmail: true,
+              submittedBy: { select: { name: true } },
+            },
+          },
+        },
+      })
+
+      let sent = 0
+      let failed = 0
+
+      // Mentor emails (coalesced per mentor).
+      const perMentor = new Map<
+        string,
+        {
+          email: string
+          name: string | null
+          projects: { id: string; title: string; teamMembers: { name: string | null; email: string }[] }[]
+        }
+      >()
+      for (const a of assignments) {
+        if (!a.mentor?.email) continue
+        const bucket = perMentor.get(a.mentorId) ?? {
+          email: a.mentor.email,
+          name: a.mentor.name,
+          projects: [],
+        }
+        bucket.projects.push({
+          id: a.project.id,
+          title: a.project.title,
+          teamMembers: a.project.teamMembers
+            .filter((tm) => tm.user?.email)
+            .map((tm) => ({ name: tm.user!.name, email: tm.user!.email })),
+        })
+        perMentor.set(a.mentorId, bucket)
+      }
+      for (const bucket of perMentor.values()) {
+        const ok = await sendMentorBulkAssignmentEmail(bucket.email, bucket.name, bucket.projects, customNote)
+        if (ok) sent++
+        else failed++
+      }
+
+      // Team emails (per project, to all members + original submitter).
+      const byProject = new Map<string, typeof assignments>()
+      for (const a of assignments) {
+        const arr = byProject.get(a.project.id) ?? []
+        arr.push(a)
+        byProject.set(a.project.id, arr)
+      }
+      for (const projAssignments of byProject.values()) {
+        const p = projAssignments[0].project
+        const mentors = projAssignments
+          .filter((a) => a.mentor?.email)
+          .map((a) => ({ name: a.mentor!.name, email: a.mentor!.email }))
+        if (mentors.length === 0) continue
+        const allMembers = p.teamMembers
+          .filter((tm) => tm.user?.email)
+          .map((tm) => ({ name: tm.user!.name, email: tm.user!.email }))
+        const recipients = new Map<string, { name: string | null }>()
+        for (const m of allMembers) recipients.set(m.email, { name: m.name })
+        if (p.submittedByEmail && !recipients.has(p.submittedByEmail)) {
+          recipients.set(p.submittedByEmail, { name: p.submittedBy?.name ?? null })
+        }
+        for (const [email, { name }] of recipients) {
+          const teammates = allMembers.filter((m) => m.email !== email)
+          const ok = await sendTeamMentorIntroductionEmail(email, name, p.title, p.id, mentors, teammates, customNote)
+          if (ok) sent++
+          else failed++
+        }
+      }
+
+      try {
+        await logAudit({
+          prisma: ctx.prisma,
+          userId: ctx.user.id,
+          action: 'MENTORSHIP_WELCOME_SENT',
+          entityType: 'Round',
+          entityId: roundId,
+          detailsJson: { sent, failed, hasCustomNote: !!customNote },
+          ipAddress: ctx.ip,
+          userAgent: ctx.userAgent,
+        })
+      } catch (err) {
+        console.error('[sendMentorshipWelcome] audit failed', err)
+      }
+
+      return { sent, failed }
+    }),
 })

src/server/services/round-engine.ts

@@ -232,7 +232,13 @@ export async function activateRound(
             id: true,
             mentorId: true,
             mentor: { select: { name: true, email: true } },
-            project: { select: { id: true, title: true } },
+            project: {
+              select: {
+                id: true,
+                title: true,
+                teamMembers: { select: { user: { select: { name: true, email: true } } } },
+              },
+            },
           },
         })
         const perMentor = new Map<
@@ -241,7 +247,7 @@ export async function activateRound(
             email: string | null
             name: string | null
             assignmentIds: string[]
-            projects: { id: string; title: string }[]
+            projects: { id: string; title: string; teamMembers: { name: string | null; email: string }[] }[]
           }
         >()
         for (const a of pendingAssignments) {
@@ -253,7 +259,13 @@ export async function activateRound(
             projects: [],
           }
           bucket.assignmentIds.push(a.id)
-          bucket.projects.push({ id: a.project.id, title: a.project.title })
+          bucket.projects.push({
+            id: a.project.id,
+            title: a.project.title,
+            teamMembers: a.project.teamMembers
+              .filter((tm) => tm.user?.email)
+              .map((tm) => ({ name: tm.user.name, email: tm.user.email })),
+          })
           perMentor.set(a.mentorId, bucket)
         }
         for (const bucket of perMentor.values()) {
@@ -336,8 +348,13 @@ export async function activateRound(
             })
           }
 
+          const allMembers = p.teamMembers
+            .filter((tm) => tm.user?.email)
+            .map((tm) => ({ name: tm.user.name, email: tm.user.email }))
+
           for (const [email, { name }] of recipients) {
-            await sendTeamMentorIntroductionEmail(email, name, p.title, p.id, mentors)
+            const teammates = allMembers.filter((m) => m.email !== email)
+            await sendTeamMentorIntroductionEmail(email, name, p.title, p.id, mentors, teammates)
           }
 
           // Stamp every mentor-assignment row so re-activation doesn't re-send.

tests/unit/mentor-welcome-email.test.ts

@@ -0,0 +1,74 @@
+import { describe, it, expect } from 'vitest'
+import {
+  getMentorBulkAssignmentTemplate,
+  getTeamMentorIntroductionTemplate,
+} from '@/lib/email'
+
+describe('getMentorBulkAssignmentTemplate', () => {
+  it('includes team-member emails, the instructions block, and a custom note', () => {
+    const t = getMentorBulkAssignmentTemplate(
+      'Alice',
+      [
+        {
+          title: 'Reef Project',
+          url: 'https://x/mentor/workspace/1',
+          teamMembers: [{ name: 'Bob', email: 'bob@team.com' }],
+        },
+      ],
+      'https://x/mentor',
+      'Reach out <b>now</b> & soon',
+    )
+    expect(t.html).toContain('bob@team.com')
+    expect(t.html).toContain('How to mentor on MOPC')
+    // The admin-supplied custom note must be HTML-escaped in the HTML body.
+    expect(t.html).toContain('&lt;b&gt;')
+    expect(t.html).not.toContain('<b>now</b>')
+    expect(t.text).toContain('bob@team.com')
+    expect(t.text).toContain('How to mentor on MOPC')
+    // The plain-text body keeps the raw note unescaped.
+    expect(t.text).toContain('Reach out <b>now</b> & soon')
+  })
+
+  it('renders without team members or note (backward compatible)', () => {
+    const t = getMentorBulkAssignmentTemplate(
+      'Alice',
+      [{ title: 'P', url: 'https://x/p' }],
+      'https://x/mentor',
+    )
+    expect(t.html).toContain('How to mentor on MOPC')
+    // Custom-note box uses the #fff7ed background; absent when no note passed.
+    expect(t.html).not.toContain('#fff7ed')
+  })
+})
+
+describe('getTeamMentorIntroductionTemplate', () => {
+  it('includes mentor + teammate emails, the instructions block, and a custom note', () => {
+    const t = getTeamMentorIntroductionTemplate(
+      'Bob',
+      'Reef Project',
+      [{ name: 'Alice', email: 'alice@mentor.com' }],
+      'https://x/applicant/mentor',
+      [{ name: 'Carol', email: 'carol@team.com' }],
+      'Welcome aboard!',
+    )
+    expect(t.html).toContain('alice@mentor.com')
+    expect(t.html).toContain('carol@team.com')
+    expect(t.html).toContain('Working with your mentor')
+    expect(t.html).toContain('Welcome aboard!')
+    // Mirror coverage on the plain-text path.
+    expect(t.text).toContain('alice@mentor.com')
+    expect(t.text).toContain('carol@team.com')
+    expect(t.text).toContain('Welcome aboard!')
+  })
+
+  it('renders without teammates or note (backward compatible)', () => {
+    const t = getTeamMentorIntroductionTemplate(
+      'Bob',
+      'Reef Project',
+      [{ name: 'Alice', email: 'alice@mentor.com' }],
+      'https://x/applicant/mentor',
+    )
+    expect(t.html).toContain('Working with your mentor')
+    expect(t.html).not.toContain('#fff7ed')
+  })
+})

tests/unit/mentorship-welcome-send.test.ts

@@ -0,0 +1,107 @@
+import { describe, it, expect, beforeAll, afterAll, vi } from 'vitest'
+
+vi.mock('@/lib/email', async () => {
+  const actual = await vi.importActual<typeof import('@/lib/email')>('@/lib/email')
+  return {
+    ...actual,
+    sendMentorBulkAssignmentEmail: vi.fn(async () => true),
+    sendTeamMentorIntroductionEmail: vi.fn(async () => true),
+  }
+})
+
+import { prisma, createCaller } from '../setup'
+import {
+  createTestProgram,
+  createTestCompetition,
+  createTestRound,
+  createTestProject,
+  createTestProjectRoundState,
+  createTestUser,
+  cleanupTestData,
+} from '../helpers'
+import { mentorRouter } from '../../src/server/routers/mentor'
+import {
+  sendMentorBulkAssignmentEmail,
+  sendTeamMentorIntroductionEmail,
+} from '@/lib/email'
+
+describe('mentor.sendMentorshipWelcome / previewMentorshipWelcome', () => {
+  let programId: string
+  const userIds: string[] = []
+  let roundId: string
+  let memberEmail: string
+  let mentorEmail: string
+
+  beforeAll(async () => {
+    const program = await createTestProgram()
+    programId = program.id
+    const competition = await createTestCompetition(program.id)
+    const round = await createTestRound(competition.id, {
+      roundType: 'MENTORING',
+      status: 'ROUND_ACTIVE',
+    })
+    roundId = round.id
+
+    const project = await createTestProject(program.id)
+    await createTestProjectRoundState(project.id, round.id)
+
+    const mentor = await createTestUser('MENTOR')
+    const member = await createTestUser('APPLICANT')
+    mentorEmail = mentor.email
+    memberEmail = member.email
+    userIds.push(mentor.id, member.id)
+
+    await prisma.teamMember.create({
+      data: { projectId: project.id, userId: member.id, role: 'LEAD' },
+    })
+    await prisma.mentorAssignment.create({
+      data: { projectId: project.id, mentorId: mentor.id, method: 'MANUAL' },
+    })
+  })
+
+  afterAll(async () => {
+    await cleanupTestData(programId, userIds)
+  })
+
+  it('sends to mentors and team members and reports counts', async () => {
+    const admin = await createTestUser('SUPER_ADMIN')
+    userIds.push(admin.id)
+    const caller = createCaller(mentorRouter, {
+      id: admin.id,
+      email: admin.email,
+      role: 'SUPER_ADMIN',
+    })
+
+    const res = await caller.sendMentorshipWelcome({ roundId, customNote: 'Reminder!' })
+
+    expect(res.sent).toBeGreaterThan(0)
+    expect(sendMentorBulkAssignmentEmail).toHaveBeenCalled()
+    expect(sendTeamMentorIntroductionEmail).toHaveBeenCalled()
+  })
+
+  it('does NOT stamp the one-time flags (re-sendable reminder)', async () => {
+    const assignment = await prisma.mentorAssignment.findFirst({
+      where: { project: { projectRoundStates: { some: { roundId } } } },
+    })
+    expect(assignment?.notificationSentAt).toBeNull()
+    expect(assignment?.teamIntroducedAt).toBeNull()
+  })
+
+  it('preview returns non-empty mentor + team HTML with real contacts', async () => {
+    const admin = await createTestUser('SUPER_ADMIN')
+    userIds.push(admin.id)
+    const caller = createCaller(mentorRouter, {
+      id: admin.id,
+      email: admin.email,
+      role: 'SUPER_ADMIN',
+    })
+
+    const pv = await caller.previewMentorshipWelcome({ roundId })
+
+    expect(pv.recipientCount).toBeGreaterThan(0)
+    expect(pv.html).toContain('Mentor version')
+    expect(pv.html).toContain('Team version')
+    expect(pv.html).toContain(memberEmail)
+    expect(pv.html).toContain(mentorEmail)
+  })
+})