ten31-database/backend/test_email_activity.py

#!/usr/bin/env python3
"""Test the email-activity proposal flow: the agent drafts PROPOSED grid notes for
newly-matched emails (going-forward only, idempotent, no grid write), and a human
approves (optionally edited -> appended to the grid) or dismisses them. The local
model is stubbed. Synthetic data only (guardrail #9).
Run: cd backend && python3 test_email_activity.py
"""
import json
import os
import sqlite3
import sys
import tempfile

os.environ["CRM_DB_PATH"] = os.path.join(tempfile.mkdtemp(), "crm.db")
os.environ.setdefault("CRM_DATA_DIR", os.path.dirname(os.environ["CRM_DB_PATH"]))
sys.path.insert(0, os.path.dirname(os.path.abspath(__file__)))
import server  # noqa: E402

server._summarize_email_gist = lambda subject, body: "fundraising update; proposed a call"

FAILS = []


def check(cond, msg):
    print(("  PASS " if cond else "  FAIL ") + msg)
    if not cond:
        FAILS.append(msg)


def setup():
    conn = sqlite3.connect(os.environ["CRM_DB_PATH"])
    conn.row_factory = sqlite3.Row
    conn.executescript("""
        CREATE TABLE app_settings (key TEXT PRIMARY KEY, value_json TEXT, updated_at TEXT);
        CREATE TABLE email_accounts (id TEXT, email_address TEXT, sync_enabled INT DEFAULT 1, sync_status TEXT, backfill_complete INT);
        CREATE TABLE emails (id TEXT PRIMARY KEY, subject TEXT, body_text TEXT, snippet TEXT, from_email TEXT, sent_at TEXT, is_matched INT, match_status TEXT);
        CREATE TABLE email_investor_links (id TEXT, email_id TEXT, fundraising_investor_id TEXT, organization_id TEXT, contact_id TEXT, match_confidence REAL);
        CREATE TABLE email_activity_proposals (id TEXT PRIMARY KEY, email_id TEXT UNIQUE, investor_id TEXT, investor_name TEXT,
            direction TEXT, summary TEXT, proposed_note TEXT, email_subject TEXT, email_date TEXT, status TEXT DEFAULT 'pending',
            decided_by TEXT, decided_at TEXT, final_note TEXT, created_at TEXT);
        CREATE TABLE users (id TEXT PRIMARY KEY, username TEXT);
        CREATE TABLE fundraising_investors (id TEXT PRIMARY KEY, investor_name TEXT, notes TEXT);
        CREATE TABLE fundraising_state (id TEXT PRIMARY KEY, grid_json TEXT, views_json TEXT, version INT,
            updated_by TEXT REFERENCES users(id), updated_at TEXT);
        CREATE TABLE interaction_log (id TEXT PRIMARY KEY, ts TEXT, actor_type TEXT, actor_id TEXT, action TEXT, target_type TEXT, target_id TEXT, payload TEXT, source TEXT, created_at TEXT);
    """)
    conn.execute("INSERT INTO users (id,username) VALUES ('user-1','grant')")
    conn.execute("INSERT INTO app_settings VALUES ('email_activity_since', ?, ?)", (json.dumps("2026-01-01T00:00:00"), "x"))
    conn.execute("INSERT INTO email_accounts (id,email_address) VALUES ('a','grant@ten31.xyz')")
    conn.execute("INSERT INTO fundraising_investors (id,investor_name,notes) VALUES ('inv1','Harbor & Vine','existing note')")
    grid = {"columns": [], "rows": [{"id": "inv1", "investor_name": "Harbor & Vine", "notes": "existing note"}]}
    conn.execute("INSERT INTO fundraising_state (id,grid_json,views_json,version) VALUES ('main',?,?,1)", (json.dumps(grid), "[]"))
    # e1 sent (from us), e2 received, both after cutoff; e3 before cutoff (excluded)
    conn.executemany("INSERT INTO emails (id,subject,body_text,from_email,sent_at,is_matched,match_status) VALUES (?,?,?,?,?,1,'matched')", [
        ("e1", "Fund III", "Here is the update", "grant@ten31.xyz", "2026-06-01T10:00:00"),
        ("e2", "Re: Fund III", "Thanks, a question", "lp@harborvine.example", "2026-06-02T10:00:00"),
        ("e3", "Old", "ancient", "lp@harborvine.example", "2025-01-01T10:00:00"),
    ])
    conn.executemany("INSERT INTO email_investor_links (id,email_id,fundraising_investor_id,match_confidence) VALUES (?,?, 'inv1', 1.0)",
                     [("l1", "e1"), ("l2", "e2"), ("l3", "e3")])
    conn.commit()
    conn.close()


def main():
    setup()

    res = server.propose_email_activity_notes()
    check(res.get("proposed") == 2, f"proposes 2 (e1,e2 after cutoff; e3 excluded), got {res}")

    res2 = server.propose_email_activity_notes()
    check(res2.get("proposed") == 0, f"idempotent: second run proposes 0, got {res2}")

    conn = server.get_db()
    props = server.list_email_activity_proposals(conn, status="pending")
    check(len(props) == 2, f"2 pending proposals listed, got {len(props)}")
    dirs = sorted(p["direction"] for p in props)
    check(dirs == ["received", "sent"], f"directions sent+received, got {dirs}")
    e1 = next(p for p in props if p["email_id"] == "e1")
    check(e1["direction"] == "sent" and "Sent" in e1["proposed_note"], "e1 (from us) is 'sent'")
    check("✉" in e1["proposed_note"] and "fundraising update" in e1["proposed_note"], "proposed note marked + has gist")

    # grid must be UNTOUCHED before approval
    grid = json.loads(conn.execute("SELECT grid_json FROM fundraising_state WHERE id='main'").fetchone()["grid_json"])
    check(grid["rows"][0]["notes"] == "existing note", "grid notes unchanged before approval")

    # approve e1 (default note) -> appended at bottom
    r = server.decide_email_activity_proposal(conn, e1["id"], "approve", "user-1")
    check(r.get("status") == "approved" and r.get("placed_in_grid") is True, f"approve places in grid, got {r}")
    grid = json.loads(conn.execute("SELECT grid_json FROM fundraising_state WHERE id='main'").fetchone()["grid_json"])
    notes = grid["rows"][0]["notes"]
    check(notes.startswith("existing note\n") and "✉" in notes, "approved note appended below existing note")

    # approve e2 with an EDITED note
    e2 = next(p for p in props if p["email_id"] == "e2")
    r2 = server.decide_email_activity_proposal(conn, e2["id"], "approve", "user-1", edited_note="Custom edited note")
    grid = json.loads(conn.execute("SELECT grid_json FROM fundraising_state WHERE id='main'").fetchone()["grid_json"])
    check("Custom edited note" in grid["rows"][0]["notes"], "edited note is what gets appended")

    # re-deciding an already-decided proposal is rejected
    r3 = server.decide_email_activity_proposal(conn, e1["id"], "dismiss", "user-1")
    check(r3.get("error") == "already_decided", f"cannot re-decide, got {r3}")

    # nothing left pending
    check(len(server.list_email_activity_proposals(conn, status="pending")) == 0, "no pending proposals remain")
    conn.close()

    if FAILS:
        print(f"\nFAILED ({len(FAILS)})")
        for f in FAILS:
            print("  - " + f)
        sys.exit(1)
    print("\nALL PASS (email-activity proposal flow)")


if __name__ == "__main__":
    main()