reference sl reply loop

Problem (root cause confirmed 2026-05-13)

SmartLead campaigns send from 6 sender mailboxes:

• (a) the operator manually opens that mailbox, or
• (b) sl_reply_ingest.py scrapes the SL Master Inbox (current cron — 15-min cadence, but discovered to have lag and gaps; e.g. Richard Shaum's 4/22 DNC reply + Amy Schmaltz's 4/22 OOO both sat unsurfaced ~21 days)

Reply-detection latency drove the 2026-05-13 manual ingest session (4 SL Master Inbox replies surfaced, including 2 actionable: Richard DNC + Amy OOO).

Confirmation that the @skyrun.com sender works correctly: Amy's 4/22 OOO autoresponder DID land in Joseph's joseph.bowens@skyrun.com Gmail because the cold email was sent from that sender. (Verified via Gmail search 2026-05-13.) Richard's 4/22 "remove me" reply did NOT land in Gmail because his cold email was sent from one of the 5 @skyrungrandcounty.com variant senders.

Solution (Option B — Workspace forwarding) — RECOMMENDED

Configure Gmail forwarding on each of the 5 @skyrungrandcounty.com mailboxes so a copy of every inbound message also lands in joseph.bowens@skyrun.com. This is the cleanest path because:

• Does NOT change SmartLead outbound headers (no From/Reply-To mismatch → preserves deliverability)
• Preserves SL Master Inbox correlation (replies still hit the sender mailbox SL polls via IMAP → AI-categorization + threading remain intact)
• Same mechanism that already proves out for joseph.bowens@skyrun.com (since that sender = Joseph's primary Gmail, replies arrive natively)
• Zero ongoing cost or maintenance (Google Workspace native feature)

Manual setup steps (per mailbox × 5)

For EACH of the 5 mailboxes — joseph@skyrungrandcounty.com, bowens@skyrungrandcounty.com, bowensbo@skyrungrandcounty.com, josephbo@skyrungrandcounty.com, joseph.bowens@skyrungrandcounty.com:

1. Sign into mail.google.com as that mailbox (use the SmartLead-stored password — visible in SL → Email Accounts → click row → General → Password field). Confirm 2-step verification path if prompted.
2. Settings (gear icon) → "See all settings" → "Forwarding and POP/IMAP" tab.
3. Click "Add a forwarding address" → enter joseph.bowens@skyrun.com → Next → Proceed → OK.
4. Google sends a confirmation email to joseph.bowens@skyrun.com. Switch to that inbox, click the confirmation link.
5. Back in the @skyrungrandcounty.com mailbox, refresh Settings → Forwarding tab. Select "Forward a copy of incoming mail to joseph.bowens@skyrun.com" and choose "keep Gmail's copy in the Inbox" (NOT "delete" — keeping the copy preserves the SL IMAP-poll path).
6. Save Changes.
7. Test: send a test email TO that @skyrungrandcounty.com mailbox from any external account. Confirm a copy appears in joseph.bowens@skyrun.com Gmail within 1-2 minutes.

Faster setup if Joseph is the Workspace admin

If Joseph (or his admin) controls the skyrungrandcounty.com Workspace at admin.google.com:

1. Sign into admin.google.com as the Workspace super-admin for skyrungrandcounty.com.
2. Apps → Google Workspace → Gmail → Default routing (or Routing).
3. Add a new rule:
- Envelope recipient: "Affects all addresses in domain skyrungrandcounty.com"
- Action: "Also deliver to" → joseph.bowens@skyrun.com → "Spam/non-spam: both" → Save.
4. Apply changes (takes up to ~1 hour to propagate). Test with one inbound message.

The Admin-Console path is ONE rule applied to all 5 mailboxes (and any future new senders Joseph adds to SL on this domain). Strongly preferred when admin access is available.

Why NOT Option A (SL Reply-To header)

Tested 2026-05-13: each SL email-account General settings page has a "Set a different reply to address" toggle. Setting it on each of the 5 @skyrungrandcounty.com accounts to point at joseph.bowens@skyrun.com would also route replies to Joseph's Gmail.

But it has two downsides:

• From/Reply-To mismatch may hurt deliverability. Spam filters (Google, Outlook, Yahoo) flag mismatched From/Reply-To as a soft phishing signal. The @skyrungrandcounty.com senders have 99-100% warmup reputation built over weeks — preserving it matters.
• Breaks SL Master Inbox IMAP-poll correlation. SL detects replies by polling the sender mailbox (the From mailbox) via IMAP. If reply-to redirects, the reply never hits the sender mailbox → SL's threading + AI-categorization may fail.

If at some point Option B is infeasible (e.g., Joseph loses access to the @skyrungrandcounty.com mailboxes), Option A becomes the fallback.

Why NOT Option C (SL webhook → CF Worker)

SmartLead supports webhook-on-reply events. A CF Worker subscriber could forward each reply payload as an email to joseph.bowens@skyrun.com. This is the most "engineered" option but:

• Requires SL webhook plan tier (not confirmed available; Joseph's SL account currently lacks API key)
• Adds infra to maintain (CF Worker, webhook secret rotation)
• Option B solves the same problem with zero infra

Re-evaluate Option C only if Joseph upgrades the SL plan AND admin-routing in Workspace becomes unavailable.

Redundancy layer — sl_reply_ingest.py extension

After Option B is configured, all SL prospect replies land in joseph.bowens@skyrun.com Gmail. The existing cron sl_reply_ingest.py continues to scrape SL Master Inbox (canonical surface — Master Inbox has AI-classified lead_category data the Gmail copy doesn't). The Gmail forward is a redundancy layer — if SL Master Inbox scrape fails (Quasar UI regression, session expiry, network), the Gmail-side mirror still catches the reply.

Extension spec

Add a new mode sl_reply_ingest.py gmail_mirror (or a sibling script sl_reply_gmail_mirror.py) that:

1. Polls Gmail (via Gmail MCP API or chrome_bridge against mail.google.com) every 15 minutes (same cadence as the SL Master Inbox scrape).
2. Search query: to:joseph.bowens@skyrun.com newer_than:1d (from:gmail.com OR from:yahoo.com OR from:hotmail.com OR ...) -in:sent -in:draft.
- Filter to messages where:
- Recipient envelope was originally a @skyrungrandcounty.com or @skyrun.com sender (use Delivered-To header or "Original-To" check)
- Sender is NOT in Joseph's domain (excludes internal traffic)
- Has a thread the sender side recognizes as a SL outbound (subject prefix match against sl_sequence_subjects.json)
3. For each match: write a pending_drafts.jsonl entry with prefix sl-gmail-mirror-<slug-email>-<date> (distinct from sl-master-inbox- to avoid collision). If the Master Inbox scrape already created a sl-reply- entry for the same email+date, mark the Gmail-mirror entry status=superseded so the PWA queue doesn't double-surface.

This way both detection paths run in parallel; failures in one don't lose replies.

Implementation deferral

The redundancy script is deferred until Option B is configured by Joseph — there's no point polling Gmail for forwarded SL replies until forwarding is active. The fix_queue entry below tracks the dependency.

Verification protocol (post-Option-B setup)

1. After Joseph confirms forwarding is configured on at least one @skyrungrandcounty.com mailbox:
2. Manually trigger a SL sequence send to a test recipient (a non-prospect address Joseph controls, e.g., his iCloud account).
3. Have the test recipient reply with "test reply 2026-XX-XX YYYYZ".
4. Within 5 min, confirm the reply lands in both:
- SL Master Inbox (visit https://app.smartlead.ai/app/master-inbox)
- joseph.bowens@skyrun.com Gmail inbox (Gmail search subject:"test reply 2026-XX-XX")
5. If both surfaces show the reply → loop closure verified for that sender. Repeat for each of the 5 senders, or once for the domain if admin-routing is used.

Standing rule (HARDWIRED 2026-05-13)

> Every SmartLead sender mailbox MUST forward to joseph.bowens@skyrun.com. The @skyrun.com primary sender is exempt (already lands natively). The 5 @skyrungrandcounty.com variants require Workspace forwarding configured per the steps above. Adding a new SL sender on @skyrungrandcounty.com (or any new domain) without forwarding = violation.

The next operator-action item Joseph needs to complete is: enable forwarding on 5 @skyrungrandcounty.com mailboxes (or one admin-routing rule). Fix-queue entry sl-reply-loop-forwarding-setup-2026-05-13 tracks until done.

Backstory (for system memory)

The 2026-05-13 manual SL Master Inbox ingest surfaced 4 replies sitting 21 days old. Two were actionable (Richard DNC, Amy OOO), two were already handled (Phil via Rachel, plus background). The latency between reply (4/22) and surfacing (5/13) is the gap this Gmail-mirror redundancy closes. Even at the cron's 15-min cadence, the SL Master Inbox scrape has occasional failure modes (Quasar regression 5/9, session expiry, chrome_bridge auth-blocked) that the Gmail-mirror covers.

Automated-setup attempt 2026-05-13 14:35Z — both paths blocked

Tried to close the loop automatically via chrome_bridge. Both Path 1 and Path 2 require operator credential entry (Joseph's hands on keyboard).

Path 1 (Admin Console default-routing) — blocked

• Navigated to https://admin.google.com/u/0/ac/home from the joseph.bowens@skyrun.com session that was already authenticated in Chrome.
• Google immediately challenged for password re-auth on the admin surface (accounts.google.com/v3/signin/challenge/pwd?continue=...admin.google.com...).
• Even if re-auth completed, joseph.bowens@skyrun.com is a member of the skyrun.com Workspace (corporate SkyRun franchisor). The skyrungrandcounty.com Workspace is the FRANCHISE tenant — joseph.bowens@skyrun.com is not bound as a super-admin there. The admin-routing path would still require a super-admin account on skyrungrandcounty.com itself (likely one of the 5 mailboxes that owns the tenant, or whoever provisioned the domain).
• Operator action: confirm which skyrungrandcounty.com account holds super-admin role. If unknown, check whoever originally provisioned the Google Workspace for skyrungrandcounty.com — typically the first user created on the tenant. That account needs to sign into admin.google.com to add the default-routing rule.

Path 2 (per-mailbox forwarding) — blocked at sign-in

• Probed Chrome for any signed-in @skyrungrandcounty.com session via accounts.google.com/AccountChooser + mail.google.com/mail/u/{1..5}/. All 5 authuser slots redirected back to u/0 (joseph.bowens@skyrun.com). Account chooser shows only joseph.bowens@skyrun.com.
• None of the 5 @skyrungrandcounty.com mailboxes are signed into this Chrome profile. Per task constraint ("don't enter passwords"), I cannot proceed past the sign-in screen.

Joseph operator-action list (use either path)

Preferred — one admin rule covers all 5 (if Joseph or a SkyRun GC owner has super-admin on the skyrungrandcounty.com Workspace):
1. Identify the super-admin account on the skyrungrandcounty.com Workspace (likely whoever provisioned the domain; could be one of the 5 mailboxes).
2. Sign into that account at admin.google.com.
3. Apps → Google Workspace → Gmail → Default routing → Add new rule → Envelope-recipient pattern: "All recipients" (or "Domain: skyrungrandcounty.com" if multi-domain) → Action: "Also deliver to → joseph.bowens@skyrun.com" → Save.
4. Wait up to 1 hour for propagation. Run the verification protocol below.

Fallback — per-mailbox Gmail forwarding (if no admin rights, or admin path takes longer than spinning up 5 forward configs):
1. In Chrome → click profile avatar → "Add another account" → enter joseph@skyrungrandcounty.com + password.
2. Repeat for bowens@, bowensbo@, josephbo@, joseph.bowens@skyrungrandcounty.com (SL stores each password under SL → Email Accounts → row → General).
3. Once all 5 are added, ping back — the automation can run the Settings → Forwarding → "Add a forwarding address" flow per mailbox, and I'll handle the verification-code retrieval from joseph.bowens@skyrun.com Gmail + the "keep copy in Inbox" radio toggle.

Cross-references

• reference_smartlead_hs_email_logging.md — Path A alias setup that gave the 5 senders HS engagement attribution
• project_smartlead_campaigns_drafted.md — 3 active SL campaigns, 209 leads
• sl_reply_ingest.py — canonical Master Inbox scrape cron
• sl_reply_gmail_mirror.py — redundancy poller; status: DORMANT (ACTIVATED=False); flip after end-to-end Workspace-forwarding test passes