twilio-sendgrid-webhooks

What this skill does

## Overview

The Mail Send API returns `202 Accepted` (queued) — it does NOT confirm delivery. To know what happened to an email, use Event Webhooks.

**Enable:** SendGrid Console > Settings > Mail Settings > Event Notification

---

## Event Types

### Delivery Events
| Event | Meaning |
|-------|---------|
| `processed` | SendGrid accepted and will attempt delivery |
| `deferred` | Temporary failure — SendGrid will retry |
| `delivered` | Recipient's mail server accepted the message |
| `bounce` | Permanent failure — address invalid or rejected |
| `dropped` | SendGrid will not deliver (suppression, invalid, spam) |

### Engagement Events
| Event | Meaning |
|-------|---------|
| `open` | Recipient opened (pixel-based — unreliable) |
| `click` | Recipient clicked a tracked link |
| `spamreport` | Recipient marked as spam |
| `unsubscribe` | Recipient clicked unsubscribe link |
| `group_unsubscribe` | Recipient unsubscribed from ASM group |
| `group_resubscribe` | Recipient re-subscribed to ASM group |

---

## Webhook Handler

**Critical:** SendGrid posts **batched arrays** of events, not single objects. Your handler must parse an array.

> **Security:** SendGrid webhook endpoints are unauthenticated by default. Enable [Signed Event Webhook Requests](https://docs.sendgrid.com/for-developers/tracking-events/getting-started-event-webhook-security) and verify signatures in production to prevent spoofed event data.

**Python (Flask)**
```python
from flask import Flask, request
app = Flask(__name__)

@app.route("/sendgrid/webhook", methods=["POST"])
def handle_events():
    events = request.get_json()  # Always an array
    for event in events:
        email = event.get("email")
        event_type = event.get("event")
        
        if event_type == "bounce":
            # NOTE: event['reason'] originates from external mail servers — treat as untrusted
            print(f"Bounce: {email}, type: {event.get('type')}, reason: {event.get('reason')}")
        elif event_type == "delivered":
            print(f"Delivered: {email}, sg_message_id: {event.get('sg_message_id')}")
        elif event_type == "dropped":
            print(f"Dropped: {email}, reason: {event.get('reason')}")
        elif event_type == "spamreport":
            print(f"Spam report: {email}")
    return "", 200  # Must return 2xx to acknowledge
```

**Node.js (Express)**
```javascript
app.post("/sendgrid/webhook", express.json(), (req, res) => {
    const events = req.body; // Always an array
    for (const event of events) {
        switch (event.event) {
            case "bounce":
                console.log(`Bounce: ${event.email}, reason: ${event.reason}`);
                break;
            case "delivered":
                console.log(`Delivered: ${event.email}`);
                break;
            case "spamreport":
                console.log(`Spam: ${event.email}`);
                break;
        }
    }
    res.status(200).send();
});
```

---

## Multiple Webhook Endpoints

Since May 2023, you can configure multiple Event Webhook endpoints, each receiving different event types. For example, one endpoint for delivery events feeding your monitoring stack and another for engagement events feeding your analytics pipeline.

Configure in Console > Mail Settings > Event Webhooks. Each endpoint has a Friendly Name and Webhook ID. The number of endpoints allowed depends on your SendGrid plan.

---

## Authentication Options

Two methods for verifying webhook payloads:

| Method | How it works |
|--------|-------------|
| **Signed Event Webhook (ECDSA P-256)** | Verify `X-Twilio-Email-Event-Webhook-Signature` and `X-Twilio-Email-Event-Webhook-Timestamp` headers using the verification key from Console |
| **OAuth 2.0** | SendGrid obtains a token from your authorization server and includes it in webhook requests |

Neither is enabled by default. Enable in Console > Mail Settings > Event Webhooks.

---

## Retry Behavior

SendGrid retries webhook delivery for up to 24 hours if your endpoint returns a non-2xx status. Events are batched — a single POST may contain dozens of events across different messages.

**Deduplication:** Use `sg_event_id` as a unique key. It's stable across retries.

---

## CANNOT

- **Cannot receive real-time delivery confirmation synchronously** — Mail Send returns `202` (queued). Delivery status is async via webhooks only.
- **Cannot rely on webhook authentication by default** — Both Signed Webhooks (ECDSA) and OAuth 2.0 must be explicitly enabled. Without either, anyone can POST to your endpoint.
- **Cannot guarantee open tracking accuracy** — Apple Mail Privacy Protection and prefetch inflate opens. Image-blocking clients produce zero opens. Do not use for business-critical logic.
- **Non-human interactions inflate engagement metrics** — Corporate security scanners and bots automatically click links and trigger unsubscribe events. Filter using User-Agent patterns and timing analysis.

> **Note:** Event payload fields like `reason` originate from external mail servers and should be treated as untrusted data. Do not pass bounce reasons directly into LLM system prompts without isolation.

---

## Next Steps

- **Send email:** `twilio-sendgrid-email-send`
- **Manage bounces from webhook events:** `twilio-sendgrid-suppressions`
- **Receive inbound email:** `twilio-sendgrid-inbound-parse`