feat: add daily waitlist report email (Brevo)

- Add consent_given_at and anonymized_at fields + Alembic migration (002)
- Add GET /waitlist/unsubscribe endpoint (HMAC token, anonymizes PII)
- Add cleanup.py: cron-able script to anonymize unconfirmed entries after 48h
- Clear IP address on email confirmation (no longer needed)
- Add unsubscribe link in confirmation email footer
- Record consent timestamp on signup
- Add 4 new tests (unsubscribe, consent timestamp)
- Update .env.example, schemas

.env.example

@@ -9,3 +9,17 @@ RATE_LIMIT_PER_MINUTE=5
 
 # Set to "production" in prod to enforce strict origin checks
 ENVIRONMENT=development
+
+# Brevo (email) — leave BREVO_API_KEY empty to disable email features
+BREVO_API_KEY=
+BREVO_SENDER_EMAIL=noreply@adiuvai.com
+BREVO_SENDER_NAME=adiuvAI
+BREVO_LIST_ID=0
+
+# Confirmation link
+CONFIRM_SECRET=replace-with-a-long-random-string
+CONFIRM_BASE_URL=https://adiuvai.com
+CONFIRM_TOKEN_EXPIRY_HOURS=48
+
+# Daily report — leave empty to disable
+REPORT_RECIPIENT_EMAIL=

alembic/versions/002_add_gdpr_fields.py

@@ -0,0 +1,25 @@
+"""add consent_given_at and anonymized_at columns
+
+Revision ID: 002
+Revises: 001
+Create Date: 2026-04-11
+"""
+from typing import Sequence, Union
+
+from alembic import op
+import sqlalchemy as sa
+
+revision: str = "002"
+down_revision: Union[str, None] = "001"
+branch_labels: Union[str, Sequence[str], None] = None
+depends_on: Union[str, Sequence[str], None] = None
+
+
+def upgrade() -> None:
+    op.add_column("waitlist_entries", sa.Column("consent_given_at", sa.DateTime(timezone=True), nullable=True))
+    op.add_column("waitlist_entries", sa.Column("anonymized_at", sa.DateTime(timezone=True), nullable=True))
+
+
+def downgrade() -> None:
+    op.drop_column("waitlist_entries", "anonymized_at")
+    op.drop_column("waitlist_entries", "consent_given_at")

app/brevo.py

@@ -0,0 +1,225 @@
+"""
+Brevo (ex-Sendinblue) integration.
+
+- Send transactional confirmation emails
+- Sync confirmed contacts to a Brevo list
+"""
+
+import logging
+
+import httpx
+
+from app.config import settings
+
+logger = logging.getLogger(__name__)
+
+BREVO_API = "https://api.brevo.com/v3"
+
+
+def _headers() -> dict[str, str]:
+    return {
+        "api-key": settings.BREVO_API_KEY,
+        "Content-Type": "application/json",
+        "Accept": "application/json",
+    }
+
+
+async def send_confirmation_email(email: str, confirm_url: str, unsubscribe_url: str = "") -> bool:
+    """Send a double opt-in confirmation email. Returns True on success."""
+    if not settings.brevo_configured:
+        logger.warning("Brevo not configured — skipping confirmation email for %s***", email[:3])
+        return False
+
+    payload = {
+        "sender": {
+            "name": settings.BREVO_SENDER_NAME,
+            "email": settings.BREVO_SENDER_EMAIL,
+        },
+        "to": [{"email": email}],
+        "subject": "Confirm your spot on the adiuvAI waitlist",
+        "htmlContent": _confirmation_html(confirm_url, unsubscribe_url),
+    }
+
+    try:
+        async with httpx.AsyncClient(timeout=10) as client:
+            resp = await client.post(f"{BREVO_API}/smtp/email", headers=_headers(), json=payload)
+            resp.raise_for_status()
+            logger.info("Confirmation email sent to %s***", email[:3])
+            return True
+    except httpx.HTTPError:
+        logger.exception("Failed to send confirmation email to %s***", email[:3])
+        return False
+
+
+async def add_contact_to_list(email: str) -> bool:
+    """Add a confirmed contact to the Brevo waitlist list. Returns True on success."""
+    if not settings.brevo_configured:
+        logger.warning("Brevo not configured — skipping contact sync for %s***", email[:3])
+        return False
+
+    if settings.BREVO_LIST_ID == 0:
+        logger.warning("BREVO_LIST_ID not set — skipping contact sync")
+        return False
+
+    payload = {
+        "email": email,
+        "listIds": [settings.BREVO_LIST_ID],
+        "updateEnabled": True,
+    }
+
+    try:
+        async with httpx.AsyncClient(timeout=10) as client:
+            resp = await client.post(f"{BREVO_API}/contacts", headers=_headers(), json=payload)
+            resp.raise_for_status()
+            logger.info("Contact synced to Brevo list %d: %s***", settings.BREVO_LIST_ID, email[:3])
+            return True
+    except httpx.HTTPError:
+        logger.exception("Failed to sync contact to Brevo: %s***", email[:3])
+        return False
+
+
+def _confirmation_html(confirm_url: str, unsubscribe_url: str = "") -> str:
+    """Email template aligned with the adiuvAI landing page brand."""
+    return f"""\
+<!DOCTYPE html>
+<html lang="en" xmlns="http://www.w3.org/1999/xhtml">
+<head>
+  <meta charset="utf-8">
+  <meta name="viewport" content="width=device-width,initial-scale=1">
+  <meta http-equiv="X-UA-Compatible" content="IE=edge">
+  <meta name="color-scheme" content="light">
+  <meta name="supported-color-schemes" content="light">
+  <title>Confirm your spot — adiuvAI</title>
+  <!--[if mso]><style>table,td{{font-family:Arial,sans-serif!important;}}</style><![endif]-->
+</head>
+<body style="margin:0;padding:0;width:100%;background-color:#f4edf3;
+  font-family:-apple-system,BlinkMacSystemFont,'Segoe UI',Roboto,'Helvetica Neue',Arial,sans-serif;
+  -webkit-font-smoothing:antialiased;-moz-osx-font-smoothing:grayscale;">
+
+  <!-- Preheader (hidden text for inbox preview) -->
+  <div style="display:none;font-size:1px;color:#f4edf3;line-height:1px;max-height:0;max-width:0;opacity:0;overflow:hidden;">
+    Confirm your email to secure your early access spot on the adiuvAI waitlist.
+  </div>
+
+  <!-- Outer wrapper -->
+  <table role="presentation" width="100%" cellpadding="0" cellspacing="0" border="0"
+         style="background-color:#f4edf3;">
+    <tr><td align="center" style="padding:48px 16px;">
+
+      <!-- Card -->
+      <table role="presentation" width="520" cellpadding="0" cellspacing="0" border="0"
+             style="max-width:520px;width:100%;background-color:#ffffff;
+               border-radius:20px;overflow:hidden;
+               box-shadow:0 4px 16px rgba(0,0,0,0.03),0 1px 2px rgba(0,0,0,0.02);">
+
+        <!-- Gold accent bar -->
+        <tr><td style="height:4px;background:linear-gradient(135deg,#fbc881 0%,#e5a94e 100%);
+          font-size:0;line-height:0;">&nbsp;</td></tr>
+
+        <!-- Logo row -->
+        <tr><td align="center" style="padding:36px 40px 0;">
+          <table role="presentation" cellpadding="0" cellspacing="0" border="0">
+            <tr>
+              <!-- Compass SVG (inline, matching the website nav-logo) -->
+              <td style="padding-right:8px;vertical-align:middle;">
+                <!--[if mso]>
+                <v:group style="width:28px;height:28px;" coordsize="64,64">
+                  <v:shape style="width:64;height:64;" path="M32,4 L48,32 L16,32 Z" fillcolor="#fbc881" stroked="f"/>
+                  <v:shape style="width:64;height:64;" path="M16,32 L48,32 L32,60 Z" fillcolor="#040404" stroked="f"/>
+                </v:group>
+                <![endif]-->
+                <!--[if !mso]><!-->
+                <svg viewBox="0 0 64 64" width="28" height="28" xmlns="http://www.w3.org/2000/svg"
+                     style="display:block;width:28px;height:28px;">
+                  <path d="M32,4 L48,32 L16,32 Z" fill="#fbc881"/>
+                  <path d="M16,32 L48,32 L32,60 Z" fill="#040404"/>
+                  <circle cx="32" cy="32" r="2.5" fill="#040404" opacity="0.18"/>
+                </svg>
+                <!--<![endif]-->
+              </td>
+              <td style="vertical-align:middle;font-size:18px;font-weight:400;
+                color:#040404;letter-spacing:-0.02em;">
+                adiuv<span style="font-weight:700;color:#e5a94e;">AI</span>
+              </td>
+            </tr>
+          </table>
+        </td></tr>
+
+        <!-- Body -->
+        <tr><td style="padding:32px 40px 0;">
+
+          <!-- Badge -->
+          <table role="presentation" cellpadding="0" cellspacing="0" border="0"
+                 style="margin:0 auto 24px;">
+            <tr><td style="padding:5px 14px;border-radius:50px;
+              background-color:rgba(251,200,129,0.12);
+              border:1px solid rgba(251,200,129,0.2);
+              font-size:11px;font-weight:600;letter-spacing:0.06em;
+              text-transform:uppercase;color:#e5a94e;">
+              &#9679;&ensp;One more step
+            </td></tr>
+          </table>
+
+          <!-- Heading -->
+          <h1 style="margin:0 0 16px;font-size:24px;font-weight:600;
+            letter-spacing:-0.03em;line-height:1.2;color:#040404;text-align:center;">
+            Confirm your spot on<br>the waitlist
+          </h1>
+
+          <!-- Paragraph -->
+          <p style="margin:0 0 28px;font-size:15px;line-height:1.7;color:#8a8ea9;
+            text-align:center;">
+            Thanks for signing up! Please confirm your email address
+            so we can keep you in the loop when adiuvAI launches.
+          </p>
+
+          <!-- CTA Button -->
+          <table role="presentation" cellpadding="0" cellspacing="0" border="0"
+                 style="margin:0 auto;">
+            <tr><td align="center" style="border-radius:50px;background-color:#040404;">
+              <a href="{confirm_url}"
+                 target="_blank"
+                 style="display:inline-block;padding:14px 36px;
+                   font-size:15px;font-weight:600;
+                   color:#fbfbfb;text-decoration:none;
+                   border-radius:50px;
+                   font-family:-apple-system,BlinkMacSystemFont,'Segoe UI',Roboto,sans-serif;">
+                Confirm my email
+              </a>
+            </td></tr>
+          </table>
+
+          <!-- Expiry note -->
+          <p style="margin:20px 0 0;font-size:13px;color:#c8c3cd;text-align:center;">
+            This link expires in {settings.CONFIRM_TOKEN_EXPIRY_HOURS} hours.
+          </p>
+
+        </td></tr>
+
+        <!-- Divider -->
+        <tr><td style="padding:32px 40px 0;">
+          <table role="presentation" width="100%" cellpadding="0" cellspacing="0" border="0">
+            <tr><td style="height:1px;background-color:#f4edf3;font-size:0;line-height:0;">&nbsp;</td></tr>
+          </table>
+        </td></tr>
+
+        <!-- Footer -->
+        <tr><td style="padding:20px 40px 32px;text-align:center;">
+          <p style="margin:0;font-size:12px;color:#c8c3cd;line-height:1.5;">
+            If you didn't sign up, simply ignore this email.
+          </p>
+          <p style="margin:8px 0 0;font-size:12px;color:#c8c3cd;">
+            <a href="https://adiuvai.com" style="color:#8a8ea9;text-decoration:underline;
+              text-underline-offset:2px;">adiuvai.com</a>
+            {f'&ensp;·&ensp;<a href="{unsubscribe_url}" style="color:#8a8ea9;text-decoration:underline;text-underline-offset:2px;">Unsubscribe</a>' if unsubscribe_url else ''}
+          </p>
+        </td></tr>
+
+      </table>
+      <!-- /Card -->
+
+    </td></tr>
+  </table>
+
+</body>
+</html>"""

app/cleanup.py

@@ -0,0 +1,58 @@
+"""
+Periodic cleanup: anonymize unconfirmed waitlist entries older than CONFIRM_TOKEN_EXPIRY_HOURS.
+
+Run as a cron job:
+    python -m app.cleanup
+
+Or integrate into docker-compose with a one-shot service.
+"""
+
+import asyncio
+import datetime
+import logging
+
+from sqlalchemy import select, and_
+
+from app.config import settings
+from app.db import async_session
+from app.models import WaitlistEntry
+from app.routes import _anonymize_entry
+
+logging.basicConfig(level=logging.INFO)
+logger = logging.getLogger(__name__)
+
+
+async def anonymize_expired() -> int:
+    """Anonymize all unconfirmed entries past the token expiry window. Returns count."""
+    cutoff = datetime.datetime.now(datetime.timezone.utc) - datetime.timedelta(
+        hours=settings.CONFIRM_TOKEN_EXPIRY_HOURS
+    )
+
+    async with async_session() as db:
+        result = await db.execute(
+            select(WaitlistEntry).where(
+                and_(
+                    WaitlistEntry.confirmed == False,  # noqa: E712
+                    WaitlistEntry.anonymized_at == None,  # noqa: E711
+                    WaitlistEntry.created_at < cutoff,
+                )
+            )
+        )
+        entries = result.scalars().all()
+
+        for entry in entries:
+            _anonymize_entry(entry)
+
+        await db.commit()
+
+    if entries:
+        logger.info("Anonymized %d expired unconfirmed entries", len(entries))
+    else:
+        logger.info("No expired unconfirmed entries to anonymize")
+
+    return len(entries)
+
+
+if __name__ == "__main__":
+    count = asyncio.run(anonymize_expired())
+    raise SystemExit(0)

app/config.py

@@ -1,3 +1,5 @@
+import secrets
+
 from pydantic_settings import BaseSettings
 
 
@@ -7,6 +9,20 @@ class Settings(BaseSettings):
     RATE_LIMIT_PER_MINUTE: int = 5
     ENVIRONMENT: str = "development"
 
+    # Brevo (email)
+    BREVO_API_KEY: str = ""
+    BREVO_SENDER_EMAIL: str = "noreply@adiuvai.com"
+    BREVO_SENDER_NAME: str = "adiuvAI"
+    BREVO_LIST_ID: int = 0  # Brevo contact list ID for waitlist subscribers
+
+    # Confirmation link
+    CONFIRM_SECRET: str = secrets.token_hex(32)  # override in production .env
+    CONFIRM_BASE_URL: str = "https://adiuvai.com"
+    CONFIRM_TOKEN_EXPIRY_HOURS: int = 48
+
+    # Daily report
+    REPORT_RECIPIENT_EMAIL: str = ""  # your email — leave empty to disable
+
     model_config = {"env_file": ".env", "env_file_encoding": "utf-8"}
 
     @property
@@ -17,5 +33,9 @@ class Settings(BaseSettings):
     def sync_database_url(self) -> str:
         return self.DATABASE_URL.replace("+asyncpg", "+psycopg2")
 
+    @property
+    def brevo_configured(self) -> bool:
+        return bool(self.BREVO_API_KEY)
+
 
 settings = Settings()

app/daily_report.py

@@ -0,0 +1,276 @@
+"""
+Daily waitlist report — sends an evening summary email via Brevo.
+
+Run as a cron job (e.g. every day at 21:00):
+    python -m app.daily_report
+
+Requires REPORT_RECIPIENT_EMAIL and BREVO_API_KEY in .env.
+"""
+
+import asyncio
+import datetime
+import logging
+
+import httpx
+from sqlalchemy import func, select, and_
+
+from app.config import settings
+from app.db import async_session
+from app.models import WaitlistEntry
+
+logging.basicConfig(level=logging.INFO)
+logger = logging.getLogger(__name__)
+
+
+async def gather_stats() -> dict:
+    """Collect today's waitlist statistics."""
+    now = datetime.datetime.now(datetime.timezone.utc)
+    today_start = now.replace(hour=0, minute=0, second=0, microsecond=0)
+
+    async with async_session() as db:
+        # Total counts
+        total = (await db.execute(select(func.count(WaitlistEntry.id)))).scalar() or 0
+
+        confirmed_total = (await db.execute(
+            select(func.count(WaitlistEntry.id)).where(WaitlistEntry.confirmed == True)  # noqa: E712
+        )).scalar() or 0
+
+        anonymized_total = (await db.execute(
+            select(func.count(WaitlistEntry.id)).where(WaitlistEntry.anonymized_at != None)  # noqa: E711
+        )).scalar() or 0
+
+        pending = total - confirmed_total - anonymized_total
+
+        # Today's activity
+        new_today = (await db.execute(
+            select(func.count(WaitlistEntry.id)).where(
+                and_(
+                    WaitlistEntry.created_at >= today_start,
+                    WaitlistEntry.anonymized_at == None,  # noqa: E711
+                )
+            )
+        )).scalar() or 0
+
+        confirmed_today = (await db.execute(
+            select(func.count(WaitlistEntry.id)).where(
+                and_(
+                    WaitlistEntry.confirmed == True,  # noqa: E712
+                    WaitlistEntry.consent_given_at >= today_start,
+                )
+            )
+        )).scalar() or 0
+
+        anonymized_today = (await db.execute(
+            select(func.count(WaitlistEntry.id)).where(
+                and_(
+                    WaitlistEntry.anonymized_at != None,  # noqa: E711
+                    WaitlistEntry.anonymized_at >= today_start,
+                )
+            )
+        )).scalar() or 0
+
+    return {
+        "date": now.strftime("%B %d, %Y"),
+        "total": total,
+        "confirmed_total": confirmed_total,
+        "pending": pending,
+        "anonymized_total": anonymized_total,
+        "new_today": new_today,
+        "confirmed_today": confirmed_today,
+        "anonymized_today": anonymized_today,
+        "conversion_rate": round(confirmed_total / total * 100, 1) if total > 0 else 0,
+    }
+
+
+async def send_report() -> bool:
+    """Gather stats and send the daily report email."""
+    if not settings.REPORT_RECIPIENT_EMAIL:
+        logger.warning("REPORT_RECIPIENT_EMAIL not set — skipping daily report")
+        return False
+
+    if not settings.brevo_configured:
+        logger.warning("Brevo not configured — skipping daily report")
+        return False
+
+    stats = await gather_stats()
+    html = _report_html(stats)
+
+    payload = {
+        "sender": {
+            "name": settings.BREVO_SENDER_NAME,
+            "email": settings.BREVO_SENDER_EMAIL,
+        },
+        "to": [{"email": settings.REPORT_RECIPIENT_EMAIL}],
+        "subject": f"Waitlist report — {stats['date']}",
+        "htmlContent": html,
+    }
+
+    headers = {
+        "api-key": settings.BREVO_API_KEY,
+        "Content-Type": "application/json",
+        "Accept": "application/json",
+    }
+
+    try:
+        async with httpx.AsyncClient(timeout=10) as client:
+            resp = await client.post(
+                "https://api.brevo.com/v3/smtp/email",
+                headers=headers,
+                json=payload,
+            )
+            resp.raise_for_status()
+            logger.info("Daily report sent to %s", settings.REPORT_RECIPIENT_EMAIL)
+            return True
+    except httpx.HTTPError:
+        logger.exception("Failed to send daily report")
+        return False
+
+
+def _report_html(s: dict) -> str:
+    """adiuvAI-branded daily report email."""
+
+    def _stat_cell(label: str, value, color: str = "#040404") -> str:
+        return f"""\
+      <td align="center" style="padding:16px 8px;">
+        <p style="margin:0;font-size:28px;font-weight:700;color:{color};
+          letter-spacing:-0.03em;line-height:1;">{value}</p>
+        <p style="margin:6px 0 0;font-size:11px;font-weight:600;color:#8a8ea9;
+          text-transform:uppercase;letter-spacing:0.06em;">{label}</p>
+      </td>"""
+
+    def _row(label: str, value, highlight: bool = False) -> str:
+        color = "#e5a94e" if highlight else "#040404"
+        return f"""\
+        <tr>
+          <td style="padding:10px 0;font-size:14px;color:#8a8ea9;border-bottom:1px solid #f4edf3;">
+            {label}
+          </td>
+          <td align="right" style="padding:10px 0;font-size:14px;font-weight:600;color:{color};
+            border-bottom:1px solid #f4edf3;">
+            {value}
+          </td>
+        </tr>"""
+
+    return f"""\
+<!DOCTYPE html>
+<html lang="en" xmlns="http://www.w3.org/1999/xhtml">
+<head>
+  <meta charset="utf-8">
+  <meta name="viewport" content="width=device-width,initial-scale=1">
+  <meta name="color-scheme" content="light">
+  <title>Waitlist Report — {s['date']}</title>
+  <!--[if mso]><style>table,td{{font-family:Arial,sans-serif!important;}}</style><![endif]-->
+</head>
+<body style="margin:0;padding:0;width:100%;background-color:#f4edf3;
+  font-family:-apple-system,BlinkMacSystemFont,'Segoe UI',Roboto,'Helvetica Neue',Arial,sans-serif;
+  -webkit-font-smoothing:antialiased;">
+
+  <div style="display:none;font-size:1px;color:#f4edf3;line-height:1px;max-height:0;max-width:0;opacity:0;overflow:hidden;">
+    {s['new_today']} new signups, {s['confirmed_total']} confirmed total ({s['conversion_rate']}% conversion)
+  </div>
+
+  <table role="presentation" width="100%" cellpadding="0" cellspacing="0" border="0"
+         style="background-color:#f4edf3;">
+    <tr><td align="center" style="padding:48px 16px;">
+
+      <table role="presentation" width="520" cellpadding="0" cellspacing="0" border="0"
+             style="max-width:520px;width:100%;background-color:#ffffff;
+               border-radius:20px;overflow:hidden;
+               box-shadow:0 4px 16px rgba(0,0,0,0.03),0 1px 2px rgba(0,0,0,0.02);">
+
+        <!-- Gold bar -->
+        <tr><td style="height:4px;background:linear-gradient(135deg,#fbc881 0%,#e5a94e 100%);
+          font-size:0;line-height:0;">&nbsp;</td></tr>
+
+        <!-- Logo -->
+        <tr><td align="center" style="padding:32px 40px 0;">
+          <table role="presentation" cellpadding="0" cellspacing="0" border="0">
+            <tr>
+              <td style="padding-right:8px;vertical-align:middle;">
+                <!--[if !mso]><!-->
+                <svg viewBox="0 0 64 64" width="24" height="24" xmlns="http://www.w3.org/2000/svg"
+                     style="display:block;width:24px;height:24px;">
+                  <path d="M32,4 L48,32 L16,32 Z" fill="#fbc881"/>
+                  <path d="M16,32 L48,32 L32,60 Z" fill="#040404"/>
+                  <circle cx="32" cy="32" r="2.5" fill="#040404" opacity="0.18"/>
+                </svg>
+                <!--<![endif]-->
+              </td>
+              <td style="vertical-align:middle;font-size:16px;font-weight:400;
+                color:#040404;letter-spacing:-0.02em;">
+                adiuv<span style="font-weight:700;color:#e5a94e;">AI</span>
+              </td>
+            </tr>
+          </table>
+        </td></tr>
+
+        <!-- Header -->
+        <tr><td style="padding:24px 40px 0;text-align:center;">
+          <p style="margin:0 0 4px;font-size:11px;font-weight:600;letter-spacing:0.06em;
+            text-transform:uppercase;color:#e5a94e;">Daily Report</p>
+          <h1 style="margin:0;font-size:22px;font-weight:600;color:#040404;
+            letter-spacing:-0.03em;">{s['date']}</h1>
+        </td></tr>
+
+        <!-- Hero stats -->
+        <tr><td style="padding:28px 40px 0;">
+          <table role="presentation" width="100%" cellpadding="0" cellspacing="0" border="0"
+                 style="background:#f4edf3;border-radius:14px;">
+            <tr>
+{_stat_cell("Confirmed", s['confirmed_total'], "#040404")}
+{_stat_cell("Pending", s['pending'], "#8a8ea9")}
+{_stat_cell("Conversion", f"{s['conversion_rate']}%", "#e5a94e")}
+            </tr>
+          </table>
+        </td></tr>
+
+        <!-- Today's activity -->
+        <tr><td style="padding:28px 40px 0;">
+          <p style="margin:0 0 12px;font-size:11px;font-weight:600;letter-spacing:0.06em;
+            text-transform:uppercase;color:#e5a94e;">Today's Activity</p>
+          <table role="presentation" width="100%" cellpadding="0" cellspacing="0" border="0">
+{_row("New signups", f"+{s['new_today']}", highlight=s['new_today'] > 0)}
+{_row("Confirmed", f"+{s['confirmed_today']}", highlight=s['confirmed_today'] > 0)}
+{_row("Anonymized (expired/unsub)", s['anonymized_today'])}
+          </table>
+        </td></tr>
+
+        <!-- Totals -->
+        <tr><td style="padding:24px 40px 0;">
+          <p style="margin:0 0 12px;font-size:11px;font-weight:600;letter-spacing:0.06em;
+            text-transform:uppercase;color:#e5a94e;">All Time</p>
+          <table role="presentation" width="100%" cellpadding="0" cellspacing="0" border="0">
+{_row("Total records", s['total'])}
+{_row("Confirmed", s['confirmed_total'], highlight=True)}
+{_row("Pending confirmation", s['pending'])}
+{_row("Anonymized", s['anonymized_total'])}
+          </table>
+        </td></tr>
+
+        <!-- Divider -->
+        <tr><td style="padding:28px 40px 0;">
+          <table role="presentation" width="100%" cellpadding="0" cellspacing="0" border="0">
+            <tr><td style="height:1px;background-color:#f4edf3;font-size:0;line-height:0;">&nbsp;</td></tr>
+          </table>
+        </td></tr>
+
+        <!-- Footer -->
+        <tr><td style="padding:16px 40px 28px;text-align:center;">
+          <p style="margin:0;font-size:12px;color:#c8c3cd;">
+            Automated report from
+            <a href="https://adiuvai.com" style="color:#8a8ea9;text-decoration:underline;
+              text-underline-offset:2px;">adiuvai.com</a>
+          </p>
+        </td></tr>
+
+      </table>
+
+    </td></tr>
+  </table>
+
+</body>
+</html>"""
+
+
+if __name__ == "__main__":
+    asyncio.run(send_report())

app/models.py

@@ -21,6 +21,12 @@ class WaitlistEntry(Base):
     ip_address: Mapped[str | None] = mapped_column(String(45), nullable=True)
     source: Mapped[str | None] = mapped_column(String(64), nullable=True)
     confirmed: Mapped[bool] = mapped_column(Boolean, default=False, server_default=sa.text("0"))
+    consent_given_at: Mapped[datetime.datetime | None] = mapped_column(
+        DateTime(timezone=True), nullable=True,
+    )
+    anonymized_at: Mapped[datetime.datetime | None] = mapped_column(
+        DateTime(timezone=True), nullable=True,
+    )
     created_at: Mapped[datetime.datetime] = mapped_column(
         DateTime(timezone=True),
         server_default=sa.text("CURRENT_TIMESTAMP"),

app/routes.py

@@ -1,13 +1,19 @@
+import asyncio
+import datetime
 import logging
 
 from fastapi import APIRouter, Depends, Request
+from fastapi.responses import HTMLResponse
 from sqlalchemy import select
 from sqlalchemy.ext.asyncio import AsyncSession
 
+from app.brevo import add_contact_to_list, send_confirmation_email
+from app.config import settings
 from app.db import get_db
 from app.rate_limit import _get_client_ip
 from app.schemas import WaitlistRequest, WaitlistResponse
 from app.models import WaitlistEntry
+from app.token import generate_token, verify_token
 
 logger = logging.getLogger(__name__)
 router = APIRouter()
@@ -25,6 +31,8 @@ async def join_waitlist(
     - Honeypot: if `website` field is non-empty, silently succeed (bot trap).
     - Duplicate emails: idempotent — returns success without error.
     - Stores the Cloudflare-resolved client IP for analytics (not exposed).
+    - Sends a confirmation email via Brevo (fire-and-forget).
+    - Records consent timestamp (GDPR Art. 7).
     """
     # Honeypot — bots fill hidden fields; silently "succeed"
     if body.website:
@@ -32,17 +40,231 @@ async def join_waitlist(
 
     email = body.email.lower().strip()
     ip = _get_client_ip(request)
+    now = datetime.datetime.now(datetime.timezone.utc)
 
     # Check for existing entry — idempotent
     existing = await db.execute(
-        select(WaitlistEntry.id).where(WaitlistEntry.email == email)
+        select(WaitlistEntry).where(WaitlistEntry.email == email)
     )
-    if existing.scalar_one_or_none() is not None:
+    entry = existing.scalar_one_or_none()
+
+    if entry is not None:
+        # Re-send confirmation if not yet confirmed (and not anonymized)
+        if not entry.confirmed and not entry.anonymized_at and settings.brevo_configured:
+            token = generate_token(email)
+            confirm_url = f"{settings.CONFIRM_BASE_URL}/api/v1/waitlist/confirm?token={token}"
+            unsub_url = f"{settings.CONFIRM_BASE_URL}/api/v1/waitlist/unsubscribe?token={token}"
+            asyncio.create_task(send_confirmation_email(email, confirm_url, unsub_url))
         return WaitlistResponse()
 
-    entry = WaitlistEntry(email=email, ip_address=ip, source="website")
+    entry = WaitlistEntry(
+        email=email,
+        ip_address=ip,
+        source="website",
+        consent_given_at=now,
+    )
     db.add(entry)
     await db.commit()
 
-    logger.info("New waitlist signup: %s", email[:3] + "***")
+    logger.info("New waitlist signup: %s***", email[:3])
+
+    # Fire-and-forget: send confirmation email via Brevo
+    if settings.brevo_configured:
+        token = generate_token(email)
+        confirm_url = f"{settings.CONFIRM_BASE_URL}/api/v1/waitlist/confirm?token={token}"
+        unsub_url = f"{settings.CONFIRM_BASE_URL}/api/v1/waitlist/unsubscribe?token={token}"
+        asyncio.create_task(send_confirmation_email(email, confirm_url, unsub_url))
+
     return WaitlistResponse()
+
+
+@router.get("/waitlist/confirm", response_class=HTMLResponse)
+async def confirm_email(
+    token: str,
+    db: AsyncSession = Depends(get_db),
+) -> HTMLResponse:
+    """
+    Double opt-in confirmation endpoint.
+
+    Verifies the HMAC token, marks the entry as confirmed,
+    and syncs the contact to Brevo.
+    """
+    email = verify_token(token)
+    if email is None:
+        return HTMLResponse(content=_result_page(success=False), status_code=400)
+
+    result = await db.execute(
+        select(WaitlistEntry).where(WaitlistEntry.email == email)
+    )
+    entry = result.scalar_one_or_none()
+    if entry is None:
+        return HTMLResponse(content=_result_page(success=False), status_code=400)
+
+    if not entry.confirmed:
+        entry.confirmed = True
+        # Clear IP now that consent is confirmed — no longer needed
+        entry.ip_address = None
+        await db.commit()
+        logger.info("Email confirmed: %s***", email[:3])
+
+        # Sync confirmed contact to Brevo list (fire-and-forget)
+        if settings.brevo_configured:
+            asyncio.create_task(add_contact_to_list(email))
+
+    return HTMLResponse(content=_result_page(success=True))
+
+
+@router.get("/waitlist/unsubscribe", response_class=HTMLResponse)
+async def unsubscribe(
+    token: str,
+    db: AsyncSession = Depends(get_db),
+) -> HTMLResponse:
+    """
+    GDPR erasure (Art. 17) — anonymize the entry.
+    Uses the same HMAC token system as confirmation.
+    """
+    email = verify_token(token)
+    if email is None:
+        return HTMLResponse(
+            content=_result_page(success=False, variant="unsubscribe"),
+            status_code=400,
+        )
+
+    result = await db.execute(
+        select(WaitlistEntry).where(WaitlistEntry.email == email)
+    )
+    entry = result.scalar_one_or_none()
+    if entry is None:
+        # Already gone — show success anyway (idempotent)
+        return HTMLResponse(content=_result_page(success=True, variant="unsubscribe"))
+
+    _anonymize_entry(entry)
+    await db.commit()
+    logger.info("Waitlist entry anonymized (unsubscribe)")
+
+    return HTMLResponse(content=_result_page(success=True, variant="unsubscribe"))
+
+
+def _anonymize_entry(entry: WaitlistEntry) -> None:
+    """Strip all PII from a waitlist entry, keeping only anonymous analytics."""
+    now = datetime.datetime.now(datetime.timezone.utc)
+    entry.email = f"anon-{entry.id}@removed.invalid"
+    entry.ip_address = None
+    entry.consent_given_at = None
+    entry.anonymized_at = now
+
+
+def _result_page(*, success: bool, variant: str = "confirm") -> str:
+    """Branded HTML response for confirmation/unsubscribe result."""
+    if variant == "unsubscribe":
+        if success:
+            title = "Data removed"
+            message = "Your personal data has been anonymized. You will not receive any further emails from us."
+            icon_bg = "rgba(251,200,129,0.12)"
+            icon_border = "rgba(251,200,129,0.25)"
+            icon_svg = '<svg viewBox="0 0 24 24" width="24" height="24" fill="none" stroke="#e5a94e" stroke-width="2.5" stroke-linecap="round" stroke-linejoin="round"><polyline points="20 6 9 17 4 12"/></svg>'
+        else:
+            title = "Invalid or expired link"
+            message = "This unsubscribe link is no longer valid. Contact privacy@adiuvai.com if you need help."
+            icon_bg = "rgba(220,38,38,0.08)"
+            icon_border = "rgba(220,38,38,0.18)"
+            icon_svg = '<svg viewBox="0 0 24 24" width="24" height="24" fill="none" stroke="#dc2626" stroke-width="2.5" stroke-linecap="round" stroke-linejoin="round"><line x1="18" y1="6" x2="6" y2="18"/><line x1="6" y1="6" x2="18" y2="18"/></svg>'
+    elif success:
+        title = "You&#8217;re confirmed!"
+        message = "Your email has been verified. We&#8217;ll notify you when adiuvAI is ready."
+        icon_bg = "rgba(251,200,129,0.12)"
+        icon_border = "rgba(251,200,129,0.25)"
+        icon_svg = '<svg viewBox="0 0 24 24" width="24" height="24" fill="none" stroke="#e5a94e" stroke-width="2.5" stroke-linecap="round" stroke-linejoin="round"><polyline points="20 6 9 17 4 12"/></svg>'
+    else:
+        title = "Invalid or expired link"
+        message = "This confirmation link is no longer valid. Please sign up again."
+        icon_bg = "rgba(220,38,38,0.08)"
+        icon_border = "rgba(220,38,38,0.18)"
+        icon_svg = '<svg viewBox="0 0 24 24" width="24" height="24" fill="none" stroke="#dc2626" stroke-width="2.5" stroke-linecap="round" stroke-linejoin="round"><line x1="18" y1="6" x2="6" y2="18"/><line x1="6" y1="6" x2="18" y2="18"/></svg>'
+
+    return f"""\
+<!DOCTYPE html>
+<html lang="en">
+<head>
+  <meta charset="utf-8">
+  <meta name="viewport" content="width=device-width,initial-scale=1">
+  <title>{title} — adiuvAI</title>
+  <style>
+    body {{
+      margin: 0; padding: 0; min-height: 100vh;
+      display: flex; align-items: center; justify-content: center;
+      background: #f4edf3;
+      font-family: -apple-system, BlinkMacSystemFont, 'Segoe UI', Roboto, sans-serif;
+      -webkit-font-smoothing: antialiased;
+    }}
+    body::before {{
+      content: '';
+      position: fixed; inset: 0;
+      background:
+        radial-gradient(ellipse 80% 60% at 25% 20%, rgba(251,200,129,0.10) 0%, transparent 60%),
+        radial-gradient(ellipse 70% 50% at 75% 70%, rgba(138,142,169,0.08) 0%, transparent 50%);
+      pointer-events: none; z-index: 0;
+    }}
+    .card {{
+      position: relative; z-index: 1;
+      text-align: center; max-width: 420px; width: 100%;
+      margin: 24px;
+      padding: 48px 40px 40px;
+      background: rgba(255,255,255,0.55);
+      backdrop-filter: blur(20px); -webkit-backdrop-filter: blur(20px);
+      border: 1px solid rgba(255,255,255,0.65);
+      border-radius: 20px;
+      box-shadow: 0 4px 16px rgba(0,0,0,0.03), 0 1px 2px rgba(0,0,0,0.02);
+    }}
+    .logo {{
+      display: inline-flex; align-items: center; gap: 8px;
+      font-size: 18px; font-weight: 400; color: #040404;
+      letter-spacing: -0.02em; margin-bottom: 28px;
+    }}
+    .logo .ai {{ font-weight: 700; color: #e5a94e; }}
+    .icon {{
+      width: 56px; height: 56px; border-radius: 50%;
+      background: {icon_bg}; border: 1.5px solid {icon_border};
+      display: flex; align-items: center; justify-content: center;
+      margin: 0 auto 20px;
+    }}
+    h1 {{
+      font-size: 22px; font-weight: 600; color: #040404;
+      letter-spacing: -0.03em; margin: 0 0 10px;
+    }}
+    p {{
+      font-size: 15px; color: #8a8ea9; line-height: 1.7;
+      margin: 0 0 28px;
+    }}
+    .btn {{
+      display: inline-block;
+      padding: 12px 28px; border-radius: 50px;
+      background: #040404; color: #fbfbfb;
+      text-decoration: none;
+      font-size: 14px; font-weight: 600;
+      transition: all 0.4s cubic-bezier(0.16, 1, 0.3, 1);
+    }}
+    .btn:hover {{
+      background: #222;
+      transform: translateY(-1px);
+      box-shadow: 0 8px 24px rgba(0,0,0,0.12);
+    }}
+  </style>
+</head>
+<body>
+  <div class="card">
+    <div class="logo">
+      <svg viewBox="0 0 64 64" width="28" height="28">
+        <path d="M32,4 L48,32 L16,32 Z" fill="#fbc881"/>
+        <path d="M16,32 L48,32 L32,60 Z" fill="#040404"/>
+        <circle cx="32" cy="32" r="2.5" fill="#040404" opacity="0.18"/>
+      </svg>
+      <span>adiuv<span class="ai">AI</span></span>
+    </div>
+    <div class="icon">{icon_svg}</div>
+    <h1>{title}</h1>
+    <p>{message}</p>
+    <a href="https://adiuvai.com" class="btn">Go to adiuvai.com</a>
+  </div>
+</body>
+</html>"""

app/schemas.py

@@ -9,4 +9,4 @@ class WaitlistRequest(BaseModel):
 
 class WaitlistResponse(BaseModel):
     ok: bool = True
-    message: str = "You're on the list!"
+    message: str = "Check your inbox for a confirmation link!"

app/token.py

@@ -0,0 +1,60 @@
+"""
+Stateless HMAC-signed confirmation tokens.
+
+Token format: base64url( email : unix_timestamp : hmac_sha256 )
+No database storage needed — the signature proves authenticity.
+"""
+
+import base64
+import hashlib
+import hmac
+import time
+
+from app.config import settings
+
+
+def generate_token(email: str) -> str:
+    """Create a URL-safe confirmation token for the given email."""
+    timestamp = str(int(time.time()))
+    payload = f"{email}:{timestamp}"
+    sig = hmac.new(
+        settings.CONFIRM_SECRET.encode(),
+        payload.encode(),
+        hashlib.sha256,
+    ).hexdigest()
+    return base64.urlsafe_b64encode(f"{payload}:{sig}".encode()).decode()
+
+
+def verify_token(token: str) -> str | None:
+    """
+    Verify a confirmation token. Returns the email if valid, None otherwise.
+    Checks both HMAC signature and expiry.
+    """
+    try:
+        decoded = base64.urlsafe_b64decode(token.encode()).decode()
+        # rsplit from the right: email may contain colons (unlikely but safe)
+        parts = decoded.rsplit(":", 2)
+        if len(parts) != 3:
+            return None
+
+        email, timestamp, sig = parts
+
+        # Verify HMAC
+        expected = hmac.new(
+            settings.CONFIRM_SECRET.encode(),
+            f"{email}:{timestamp}".encode(),
+            hashlib.sha256,
+        ).hexdigest()
+        if not hmac.compare_digest(sig, expected):
+            return None
+
+        # Check expiry
+        age_seconds = time.time() - int(timestamp)
+        if age_seconds > settings.CONFIRM_TOKEN_EXPIRY_HOURS * 3600:
+            return None
+        if age_seconds < 0:
+            return None  # future timestamp — tampered
+
+        return email
+    except Exception:
+        return None

requirements.txt

@@ -8,3 +8,4 @@ pydantic>=2.0,<3.0
 pydantic-settings>=2.0,<3.0
 email-validator>=2.0,<3.0
 python-dotenv>=1.0,<2.0
+httpx>=0.27,<1.0

tests/test_waitlist.py

@@ -1,12 +1,17 @@
+import time
+from unittest.mock import AsyncMock, patch
+
 import pytest
 import pytest_asyncio
 from httpx import ASGITransport, AsyncClient
+from sqlalchemy import select
 from sqlalchemy.ext.asyncio import AsyncSession, async_sessionmaker, create_async_engine
 
 from app.main import app
-from app.models import Base
+from app.models import Base, WaitlistEntry
 from app.db import get_db
 from app.rate_limit import _hits_store
+from app.token import generate_token, verify_token
 
 # Use SQLite for tests (no Postgres dependency)
 TEST_DB_URL = "sqlite+aiosqlite:///./test_waitlist.db"
@@ -52,7 +57,7 @@ async def test_join_waitlist_success(client):
     assert resp.status_code == 200
     data = resp.json()
     assert data["ok"] is True
-    assert "list" in data["message"].lower()
+    assert "inbox" in data["message"].lower()
 
 
 @pytest.mark.asyncio
@@ -107,3 +112,178 @@ async def test_rate_limit(client):
     # The 6th request should be rate-limited (limit is 5)
     assert resp.status_code == 429
     assert "Retry-After" in resp.headers
+
+
+# ── Confirmation token tests ─────────────────────────────────────────
+
+
+@pytest.mark.asyncio
+async def test_token_roundtrip():
+    """A generated token should verify back to the same email."""
+    email = "token@example.com"
+    token = generate_token(email)
+    assert verify_token(token) == email
+
+
+@pytest.mark.asyncio
+async def test_token_expired():
+    """An expired token should return None."""
+    email = "expired@example.com"
+    with patch("app.token.time") as mock_time:
+        # Generate token "49 hours ago"
+        past = time.time() - 49 * 3600
+        mock_time.time.return_value = past
+        token = generate_token(email)
+
+    # Now verify with real time — should be expired (>48h)
+    assert verify_token(token) is None
+
+
+@pytest.mark.asyncio
+async def test_token_tampered():
+    """A tampered token should return None."""
+    token = generate_token("legit@example.com")
+    # Flip a character in the token
+    tampered = token[:-1] + ("A" if token[-1] != "A" else "B")
+    assert verify_token(tampered) is None
+
+
+# ── Confirm endpoint tests ───────────────────────────────────────────
+
+
+@pytest.mark.asyncio
+async def test_confirm_valid_token(client, db_session):
+    """GET /confirm with valid token marks email as confirmed and clears IP."""
+    # Seed an unconfirmed entry
+    entry = WaitlistEntry(email="confirm@example.com", source="website", ip_address="1.2.3.4")
+    db_session.add(entry)
+    await db_session.commit()
+
+    token = generate_token("confirm@example.com")
+    resp = await client.get(f"/api/v1/waitlist/confirm?token={token}")
+    assert resp.status_code == 200
+    assert "confirmed" in resp.text.lower() or "verified" in resp.text.lower()
+
+    # Verify DB state
+    result = await db_session.execute(
+        select(WaitlistEntry).where(WaitlistEntry.email == "confirm@example.com")
+    )
+    confirmed_entry = result.scalar_one()
+    assert confirmed_entry.confirmed is True
+    assert confirmed_entry.ip_address is None  # IP cleared on confirm
+
+
+@pytest.mark.asyncio
+async def test_confirm_invalid_token(client):
+    """GET /confirm with invalid token returns 400."""
+    resp = await client.get("/api/v1/waitlist/confirm?token=garbage")
+    assert resp.status_code == 400
+    assert "invalid" in resp.text.lower() or "expired" in resp.text.lower()
+
+
+@pytest.mark.asyncio
+async def test_confirm_idempotent(client, db_session):
+    """Confirming an already confirmed email returns 200 (idempotent)."""
+    entry = WaitlistEntry(email="idem@example.com", source="website", confirmed=True)
+    db_session.add(entry)
+    await db_session.commit()
+
+    token = generate_token("idem@example.com")
+    resp = await client.get(f"/api/v1/waitlist/confirm?token={token}")
+    assert resp.status_code == 200
+
+
+@pytest.mark.asyncio
+async def test_confirm_unknown_email(client):
+    """Token for a non-existent email returns 400."""
+    token = generate_token("unknown@example.com")
+    resp = await client.get(f"/api/v1/waitlist/confirm?token={token}")
+    assert resp.status_code == 400
+
+
+# ── Brevo integration tests (mocked) ────────────────────────────────
+
+
+@pytest.mark.asyncio
+async def test_signup_triggers_confirmation_email(client, db_session):
+    """When Brevo is configured, signup sends a confirmation email."""
+    with patch("app.routes.settings") as mock_settings, \
+         patch("app.routes.send_confirmation_email", new_callable=AsyncMock) as mock_send:
+        mock_settings.brevo_configured = True
+        mock_settings.CONFIRM_BASE_URL = "http://test"
+
+        resp = await client.post(
+            "/api/v1/waitlist",
+            json={"email": "brevo@example.com"},
+        )
+        assert resp.status_code == 200
+
+        # Wait for fire-and-forget task
+        import asyncio
+        await asyncio.sleep(0.1)
+
+        mock_send.assert_called_once()
+        call_args = mock_send.call_args
+        assert call_args[0][0] == "brevo@example.com"
+        assert "confirm" in call_args[0][1]
+
+
+# ── Unsubscribe / anonymize tests ────────────────────────────────────
+
+
+@pytest.mark.asyncio
+async def test_unsubscribe_anonymizes_entry(client, db_session):
+    """GET /unsubscribe with valid token anonymizes the entry."""
+    entry = WaitlistEntry(email="unsub@example.com", source="website", confirmed=True)
+    db_session.add(entry)
+    await db_session.commit()
+    entry_id = entry.id
+
+    token = generate_token("unsub@example.com")
+    resp = await client.get(f"/api/v1/waitlist/unsubscribe?token={token}")
+    assert resp.status_code == 200
+    assert "removed" in resp.text.lower() or "anonymized" in resp.text.lower()
+
+    # Verify anonymization
+    result = await db_session.execute(
+        select(WaitlistEntry).where(WaitlistEntry.id == entry_id)
+    )
+    anon = result.scalar_one()
+    assert anon.email == f"anon-{entry_id}@removed.invalid"
+    assert anon.ip_address is None
+    assert anon.consent_given_at is None
+    assert anon.anonymized_at is not None
+
+
+@pytest.mark.asyncio
+async def test_unsubscribe_invalid_token(client):
+    """GET /unsubscribe with invalid token returns 400."""
+    resp = await client.get("/api/v1/waitlist/unsubscribe?token=garbage")
+    assert resp.status_code == 400
+
+
+@pytest.mark.asyncio
+async def test_unsubscribe_already_gone(client):
+    """GET /unsubscribe for non-existent entry returns 200 (idempotent)."""
+    token = generate_token("gone@example.com")
+    resp = await client.get(f"/api/v1/waitlist/unsubscribe?token={token}")
+    assert resp.status_code == 200
+
+
+# ── Consent timestamp tests ──────────────────────────────────────────
+
+
+@pytest.mark.asyncio
+async def test_signup_records_consent_timestamp(client, db_session):
+    """New signup records consent_given_at."""
+    resp = await client.post(
+        "/api/v1/waitlist",
+        json={"email": "consent@example.com"},
+    )
+    assert resp.status_code == 200
+
+    result = await db_session.execute(
+        select(WaitlistEntry).where(WaitlistEntry.email == "consent@example.com")
+    )
+    entry = result.scalar_one()
+    assert entry.consent_given_at is not None