#!/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()