Skip to content

AI Re-Engagement Feature

Overview

AI Re-Engagement uses AI to automatically re-open Messenger and Instagram conversations before Meta's 24-hour customer-service window closes. The system generates personalised, context-aware nudge messages that drive customer replies and keep conversations active.

  • Re-engagement monitor: /reengagement — shows recent nudges sent, timestamps, reasons, and status.
  • Settings: Settings → AI & Automation → AI Re-Engagement tab.

Features

1. AI-Powered Nudge Generation

Smart Drafting: - AI analyses conversation context, contact history, deal stage, and tags - Generates personalised nudge messages per conversation - Adapts tone based on settings (Friendly / Formal / Casual) - References prior messages, products discussed, and open deals

Context Awareness: - Reads last 10 messages for context - Considers contact tags (e.g., hot_lead, awaiting_customer) - Checks associated deal stage and value - Incorporates contact name and preferences

2. Channel Support

Supported Channels: - Facebook Messenger - Instagram Direct

Not Supported: - WhatsApp (uses approved templates separately) - Telegram - TikTok - LinkedIn - Email

3. Trigger Configuration

Timing Controls: - Default trigger: 20 hours after customer's last message - Configurable range: 12–23 hours - Hard stop: never sends after last_user_message_at + 24h - Respects Meta's 24-hour customer-service window

Channel Selection: - Enable per channel (Messenger, Instagram, or both) - Independent toggle per channel

4. Safety & Limits

Rate Limiting: - Maximum 1 nudge per 24-hour window per conversation (DB-enforced) - 3 consecutive unanswered nudges auto-disable re-engagement on that conversation - Customer reply resets the counter and marks open nudges as user_replied - Per-conversation kill switch in the inbox UI

Opt-Out Compliance: - Automatically honours customer opt-outs - Unsubscribe status checked before sending - All nudges logged as AI_REENGAGEMENT_SENT activity events

5. Approval Mode

Agent Review Workflow: - Optional Require agent approval setting - AI drafts appear in inbox as review cards - Actions per draft: - Approve — sends the AI-generated message - Edit — modify text before sending - Skip — reject draft, prevent another nudge for that window - Editing replaces AI text and sends immediately

6. AI Provider Options

ConnectGain AI (Default): - Powered by Gemini 2.5 Flash via Lovable AI Gateway

BYOK — Bring Your Own Gemini Key (Free): - Use your own Google AI Studio API key - Key encrypted at rest, never returned to the browser - Scope selection: - All AI features — chatbots, classification, translations, drafts, summaries, and re-engagement - Re-engagement only - Fallback toggle: temporarily use ConnectGain AI if your key fails

7. Access Control

Admin Controls: - OWNER / ADMIN: enable, configure, set BYOK - AGENT: approve / edit / skip drafts (when approval mode is on)

8. Activity Logging

Audit Trail: - Every nudge logged as AI_REENGAGEMENT_SENT activity event - Draft status tracked: draft, sent, user_replied, skipped, failed - Nudge drafts and outcomes retained 90 days, then anonymised - PII scrubbed from Sentry breadcrumbs

Use Cases

Use Case 1: Abandoned Cart Recovery on Messenger

Scenario: Online shopper asked about a product, was sent options, then went quiet.

Setup: 1. Go to Settings → AI & Automation → AI Re-Engagement 2. Toggle Enable 3. Set threshold to 20 hours 4. Enable Messenger channel 5. Set tone to Friendly 6. Save

Expected Outcome: 20 hours after the customer's last message, AI sends a personalised nudge like:

Hi Sara — still thinking about the navy linen dress? I can hold your size for the next few hours if you'd like. Want me to send the checkout link?

Expected Uplift: +15–25% recovered carts on Meta DMs.

Use Case 2: Instagram Lead Follow-Up

Scenario: IG follower DM'd "info?" on a sponsored post but never replied after the agent answered.

Setup: 1. Enable AI Re-Engagement 2. Set threshold to 18 hours 3. Enable Instagram channel 4. Set tone to Casual 5. Turn on Require agent approval (for high-value leads)

Expected Outcome: AI drafts a follow-up message:

Hey Jamal 👋 just wanted to make sure you saw the pricing I sent. Happy to set up a quick call or share the demo link — whichever works?

Agent reviews and approves. Message sent before 24h window closes.

Expected Uplift: +30% qualified-lead conversion.

Use Case 3: Real-Estate Inquiry Rescue

Scenario: Buyer asked about a listing on Messenger then went silent. Conversation tagged hot_lead.

Setup: 1. Enable AI Re-Engagement 2. Set threshold to 22 hours 3. Enable Messenger 4. Set tone to Formal

Expected Outcome:

Hi Ahmed — the 3-bedroom in Sheikh Zayed is still available, and there's a viewing slot tomorrow at 5pm. Want me to book it for you?

Expected Uplift: +20% viewing bookings.

Use Case 4: Support Warm Reminder Before SLA Breach

Scenario: Customer reported an issue, support replied, customer never confirmed resolution.

Setup: 1. Enable AI Re-Engagement 2. Set threshold to 21 hours 3. Tag conversation awaiting_customer 4. Set tone to Friendly

Expected Outcome:

Hi Lina, just checking in — did the reset link I sent earlier solve the login issue? If not, I can hop on a quick call.

Expected Uplift: Fewer reopened tickets, higher CSAT.

Use Case 5: Sequence Safety-Net on Meta

Scenario: Contact mid-way through a Messenger drip sequence who stopped responding.

Setup: 1. Enable AI Re-Engagement alongside Sequences 2. Set threshold to 20 hours 3. Enable Messenger

Expected Outcome:

Hey Omar — wanted to circle back on what we discussed. Any questions I can answer before our next step?

Expected Uplift: Recovers ~12% of dropped sequences without breaking Meta policy.

Test Cases

Test Case 1: Enable AI Re-Engagement

Test: Verify activation and first nudge

Steps: 1. Go to Settings → AI & Automation → AI Re-Engagement 2. Toggle Enable 3. Set threshold to 20 hours 4. Select Messenger channel 5. Choose Friendly tone 6. Save settings 7. Create a test conversation on Messenger 9. Wait 20 hours (or trigger test mode) 10. Verify AI nudge draft generated 11. Verify nudge sent (or appears for approval)

Expected Result: AI Re-Engagement active; nudge generated and sent within configured window.

Test Case 2: Agent Approval Workflow

Test: Verify approval mode

Steps: 1. Enable Require agent approval 2. Trigger a re-engagement scenario 3. Verify draft card appears in inbox 4. Click Edit, modify message text 5. Click Send 6. Verify custom message delivered 7. Trigger another scenario 8. Click Skip 9. Verify no nudge sent and window blocked

Expected Result: Agent can edit, approve, or skip drafts. Skipped conversations blocked for that window.

Test Case 3: BYOK Configuration

Test: Verify BYOK setup

Steps: 1. Get a key from Google AI Studio 2. Go to Settings → AI → AI Provider 3. Select My Google Gemini key (BYOK) 4. Paste key, pick model 5. Click Test 6. Set scope to Re-engagement only 7. Save 8. Trigger re-engagement 9. Verify nudge uses BYOK key

Expected Result: BYOK configured; re-engagement uses org's own Gemini key.

Test Case 4: 3-Strike Auto-Disable

Test: Verify safety limit

Steps: 1. Enable AI Re-Engagement 2. Find a conversation with 3 consecutive unanswered nudges 3. Verify conversation auto-paused (re-engagement disabled) 4. Verify manual re-enable required in inbox

Expected Result: After 3 unanswered nudges, re-engagement auto-disabled on that conversation.

Test Case 5: 24h Window Compliance

Test: Verify Meta policy compliance

Steps: 1. Create a Messenger conversation 2. Send customer message 3. Wait until 24h+1 minute after last customer message 4. Verify AI Re-Engagement does NOT send nudge 5. Verify log shows "Window expired"

Expected Result: No nudge sent after 24-hour window. Compliance enforced.

Document Version: 1.0.0 Last Updated: June 2026