Gate (run first)

Inputs (ask if missing)

• Contact: name, email, or LinkedIn-style identifier; company (optional but helps disambiguate).
• Scope: default = relevant threads in the last ~12 months; user may narrow or widen. For calendar: default = past ~12 months plus upcoming ~6 months (or tool default) so scheduled meetings with the contact are included.

User said they sent — trust them (default)

If the user says they sent an email (or it bounced / failed / wrong address), believe them. Do not spend the session trying to prove delivery or find a bounce/NDR via the Gmail MCP — it is a poor fit for that (operators often don’t apply; results can look like random Inbox/Sent).

Instead, pivot immediately to helping them find a correct email address (or a short list of evidence-backed candidates) for this contact:

1. tracker.json / profile.md — any stored email, title, or company for this person.
2. Mail search that does work on MCP: plain Firstname Lastname, company, to: / from: with a simple address or domain (one clause at a time). Look at Sent and Inbox for real threads (signatures, forwards, calendar invites), not mailer-daemon unless the user explicitly asks you to hunt a bounce.
3. Reasonable variants — alternate domains (parent vs subsidiary), first.last, firstlast, flast — label each as guess vs cited from a source.
4. Ask the user to paste an address from LinkedIn, the company site, or a prior reply when the connector can’t confirm.
5. Put candidates and confidence in email_address_notes; explain in search_method_notes that bounce search was skipped (MCP limitation) and the user’s send attempt is taken at their word.

Optional bounce lookup: Only if the user explicitly asks you to find the bounce message and approves spending time on it: try from:mailer-daemon (single token) and read a few recent system messages for this address/name — but do not treat “no result” as proof of anything. Prefer the user pasting the bounce from Gmail web if needed.

Name search (when the thread isn’t found)

If step 2 (below) doesn’t surface a clear thread, search mail for the contact’s full name as plain text (e.g. Jordan Kim), then name + company. Prefer All Mail / broad scope when the tool allows.

Workflow

1. Read {user_dir}/CareerNavigator/profile.md and tracker.json (applications[].contacts[], networking[]) for any known facts about this person—do not contradict tracker evidence. If inbox tools are missing in this session, skip mail search below and note in caveats. If calendar tools are missing, skip the calendar step and set calendar_notes, upcoming_meetings, and warm_networking to "—" or not searched — no calendar tools as appropriate.
2. With approval, use host Gmail / Microsoft 365 tools to search and read relevant threads (by address, domain, company, plain name). Read-only: do not send, draft, or delete mail. Skip if step 1 determined there are no inbox tools.
3. Calendar (when tools exist and approval includes calendar): Use Google Calendar and/or Microsoft 365 calendar tools to find events where the contact appears as attendee (email match) or title/description/location plausibly reference the person or company. Cover:
   • Past: events that already occurred in the lookback window (default ~12 months)—commitments or next steps in notes/description.
   • Scheduled / upcoming: events from today forward through the forward window (default ~6 months or host limit)—date, time (if available), title. These support warm networking identification: if a meeting is scheduled with this contact, treat the thread as warm and pass that signal to hooks_for_writer (e.g. “Upcoming 1:1 Thu—short ping to confirm or share prep,” not a cold intro). Read-only: do not create, move, or delete events unless the user explicitly asks outside this skill’s scope.
4. If the user says they sent mail (failed delivery, wrong address, or “I already emailed them”): follow “User said they sent — trust them (default)” above — address resolution first; no mandatory bounce/NDR hunt via MCP.
5. Name fallback: If mail search did not surface a clear thread and the user did not frame this as “I sent / bad address,” run “Name search (when the thread isn’t found)” above.
6. Summarize neutrally: who wrote last, dates, commitments, open loops, tone; plus any calendar findings (past calls/interviews; upcoming scheduled meetings—highlight these for warm identification). Quote sparingly; prefer bullets.
7. Emit a ContactContextBrief (markdown block below) for writer / draft-outreach.
8. Offer: “Want draft-outreach next with this context folded in?” If yes, pass the brief into the next step (user can run /career-navigator:draft-outreach or continue in chat).

ContactContextBrief (output block)

## ContactContextBrief
- **contact:** {name or best label}
- **company:** {company or "—"}
- **sources_used:** gmail | microsoft_365 | calendar | none (list all that were actually queried)
- **as_of:** {YYYY-MM-DD}
- **summary:** {2–6 bullets: substance of prior exchanges and, if used, calendar context}
- **calendar_notes:** {**Past** meetings with this contact—dates, titles, commitments from descriptions—or "—" if none}
- **upcoming_meetings:** {**Scheduled** future events with this contact—date, time if known, title—or "—" if none / not searched}
- **warm_networking:** {one line: e.g. `warm — upcoming meeting scheduled` | `warm — past 1:1 only` | `uncertain — calendar partial` | `cold — no calendar match`}
- **open_loops:** {promises, unanswered threads, deadlines mentioned—in mail or calendar; include prep/follow-up for **upcoming** meetings when relevant}
- **hooks_for_writer:** {3 bullets—factual, safe to reference in outreach}
- **email_address_notes:** {candidate addresses for this contact—evidence-backed vs tentative—or "—"}
- **search_method_notes:** {e.g. user confirmed they sent mail; bounce hunt skipped; MCP limits—or "—"}
- **caveats:** {e.g. partial search, connector limits}

Constraints

• Honest: Do not invent threads or addresses. Label guesses clearly.
• User-sent: If the user says they sent email, do not contradict them for lack of bounce proof via MCP.
• Privacy: do not paste full bodies unless needed; respect sensitive content.
• Calendar enrichment only when tools exist and the user approved calendar scope (combined approval is fine unless the host requires a separate calendar consent step).

Scheduling

Optional /schedule before high-stakes outreach weeks; usually on-demand before draft-outreach.