ten31-database/backend/email_integration/test_email_activity_panel.py

#!/usr/bin/env python3
"""Test the admin-only email-activity panel (Communications tab, v0.1.0:80).

Covers the pure query (`db.query_email_activity`): investor/mailbox/search/direction
filters, per-sighting soft-delete, direction at the email level, mailbox + investor
roll-ups (incl. unmatched fallback to the matched address), and the filter facets.
Also asserts the route handler enforces admin server-side. Synthetic data only.

Run: cd backend && python3 email_integration/test_email_activity_panel.py
"""
import os
import sqlite3
import sys

sys.path.insert(0, os.path.dirname(os.path.dirname(os.path.abspath(__file__))))
from email_integration import db as _db  # noqa: E402

FAILS = []


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


def make_db():
    conn = sqlite3.connect(":memory:")
    conn.row_factory = sqlite3.Row
    conn.executescript("""
        CREATE TABLE email_accounts (id TEXT PRIMARY KEY, email_address TEXT);
        CREATE TABLE emails (id TEXT PRIMARY KEY, subject TEXT, from_name TEXT, from_email TEXT,
            sent_at TEXT, snippet TEXT, has_attachments INT DEFAULT 0, is_matched INT DEFAULT 0,
            match_status TEXT DEFAULT 'unmatched');
        CREATE TABLE email_account_messages (id TEXT PRIMARY KEY, email_id TEXT, account_id TEXT,
            is_sent INT DEFAULT 0, deleted_at TEXT);
        CREATE TABLE email_investor_links (id TEXT PRIMARY KEY, email_id TEXT,
            fundraising_investor_id TEXT, fundraising_contact_id TEXT, matched_address TEXT);
        CREATE TABLE fundraising_investors (id TEXT PRIMARY KEY, investor_name TEXT, graveyard INTEGER DEFAULT 0);
        CREATE TABLE fundraising_contacts (id TEXT PRIMARY KEY, investor_id TEXT, full_name TEXT);
    """)
    # Two mailboxes (us), three investors (one reached only via a contact link;
    # one graveyarded but still with captured email history).
    conn.executemany("INSERT INTO email_accounts VALUES (?,?)", [
        ("acc-grant", "grant@ten31.xyz"),
        ("acc-jon", "jonathan@ten31.xyz"),
    ])
    conn.executemany("INSERT INTO fundraising_investors VALUES (?,?,?)", [
        ("inv-harbor", "Harbor & Vine", 0),
        ("inv-pacific", "Pacific Capital", 0),
        ("inv-dead", "Dead Deal LP", 1),
    ])
    conn.execute("INSERT INTO fundraising_contacts VALUES ('fc-1','inv-pacific','Sarah Williams')")
    # Emails:
    #  e1 outbound (from us) -> Harbor, seen by grant
    #  e2 inbound (from LP)  -> Harbor, seen by grant + jonathan
    #  e3 inbound (from LP)  -> Pacific via contact link, seen by jonathan
    #  e4 inbound, UNMATCHED (no investor link), seen by grant
    #  e5 inbound, only sighting is tombstoned -> must be excluded
    conn.executemany(
        "INSERT INTO emails (id,subject,from_name,from_email,sent_at,snippet,has_attachments,is_matched,match_status) VALUES (?,?,?,?,?,?,?,?,?)",
        [
            ("e1", "Fund III update", "Grant", "grant@ten31.xyz", "2026-06-05T10:00:00", "here is the deck", 1, 1, "matched"),
            ("e2", "Re: Fund III update", "LP Harbor", "lp@harborvine.example", "2026-06-06T09:00:00", "thanks, one question", 0, 1, "matched"),
            ("e3", "Intro", "Sarah Williams", "sarah@pacificcap.example", "2026-06-07T08:00:00", "would love to chat", 0, 1, "matched"),
            ("e4", "Cold inbound", "Random", "noreply@spam.example", "2026-06-08T08:00:00", "buy now", 0, 0, "unmatched"),
            ("e5", "Deleted thread", "Ghost", "ghost@x.example", "2026-06-09T08:00:00", "gone", 0, 1, "matched"),
            ("e6", "Old dead-deal thread", "Dead LP", "lp@deaddeal.example", "2026-06-01T00:00:00", "we passed", 0, 1, "matched"),
        ])
    conn.executemany(
        "INSERT INTO email_account_messages (id,email_id,account_id,is_sent,deleted_at) VALUES (?,?,?,?,?)",
        [
            ("m1", "e1", "acc-grant", 1, None),
            ("m2", "e2", "acc-grant", 0, None),
            ("m3", "e2", "acc-jon", 0, None),
            ("m4", "e3", "acc-jon", 0, None),
            ("m5", "e4", "acc-grant", 0, None),
            ("m6", "e5", "acc-grant", 0, "2026-06-10T00:00:00"),  # tombstoned
            ("m7", "e6", "acc-grant", 0, None),
        ])
    conn.executemany(
        "INSERT INTO email_investor_links (id,email_id,fundraising_investor_id,fundraising_contact_id,matched_address) VALUES (?,?,?,?,?)",
        [
            ("l1", "e1", "inv-harbor", None, "lp@harborvine.example"),
            ("l2", "e2", "inv-harbor", None, "lp@harborvine.example"),
            ("l3", "e3", None, "fc-1", "sarah@pacificcap.example"),
            ("l5", "e5", "inv-harbor", None, "lp@harborvine.example"),
            ("l6", "e6", "inv-dead", None, "lp@deaddeal.example"),
        ])
    conn.commit()
    return conn


def ids(res):
    return [e["id"] for e in res["emails"]]


def main():
    conn = make_db()

    # --- baseline: live emails only, newest first, tombstoned excluded ---
    res = _db.query_email_activity(conn)
    check(ids(res) == ["e4", "e3", "e2", "e1", "e6"], f"live emails newest-first, e5 (tombstoned) excluded; got {ids(res)}")
    check(res["count"] == 5 and res["truncated"] is False, "count + not truncated")

    # --- direction at the email level ---
    e1 = next(e for e in res["emails"] if e["id"] == "e1")
    e2 = next(e for e in res["emails"] if e["id"] == "e2")
    check(e1["direction"] == "outbound", "e1 from our mailbox -> outbound")
    check(e2["direction"] == "inbound", "e2 from LP -> inbound")
    check(_db.query_email_activity(conn, direction="outbound")["emails"][0]["id"] == "e1"
          and len(_db.query_email_activity(conn, direction="outbound")["emails"]) == 1,
          "direction=outbound returns only e1")
    check(ids(_db.query_email_activity(conn, direction="inbound")) == ["e4", "e3", "e2", "e6"],
          "direction=inbound excludes the outbound e1")

    # --- mailbox roll-up + per-account filter ---
    check(set(e2["mailboxes"]) == {"grant@ten31.xyz", "jonathan@ten31.xyz"}, "e2 seen by both mailboxes")
    check(ids(_db.query_email_activity(conn, account_id="acc-jon")) == ["e3", "e2"],
          "account_id=acc-jon returns only emails that mailbox saw")

    # --- investor filter: direct link and via-contact link ---
    check(set(ids(_db.query_email_activity(conn, investor_id="inv-harbor"))) == {"e2", "e1"},
          "investor_id=inv-harbor -> e1,e2")
    check(ids(_db.query_email_activity(conn, investor_id="inv-pacific")) == ["e3"],
          "investor_id=inv-pacific resolved through fundraising_contacts -> e3")

    # --- investor name roll-up + unmatched fallback ---
    check(e1["investors"] == [{"id": "inv-harbor", "name": "Harbor & Vine"}], "e1 investor resolved to name")
    e3 = next(e for e in res["emails"] if e["id"] == "e3")
    check(e3["investors"] == [{"id": "inv-pacific", "name": "Pacific Capital"}], "e3 investor resolved via contact")
    e4 = next(e for e in res["emails"] if e["id"] == "e4")
    check(e4["investors"] == [] and e4["investor_labels"] == [], "e4 unmatched -> no investor, no link")

    # --- free-text search over subject / snippet / sender ---
    check(set(ids(_db.query_email_activity(conn, search="Fund III"))) == {"e1", "e2"}, "search subject")
    check(ids(_db.query_email_activity(conn, search="pacificcap")) == ["e3"], "search sender address")
    check(ids(_db.query_email_activity(conn, search="buy now")) == ["e4"], "search snippet")

    # --- facets ---
    check([a["email_address"] for a in res["accounts"]] == ["grant@ten31.xyz", "jonathan@ten31.xyz"],
          "accounts facet sorted")
    facet_inv = {i["id"] for i in res["investors"]}
    check(facet_inv == {"inv-harbor", "inv-pacific"}, "investor facet covers direct + via-contact activity")

    # --- graveyard: hidden from the picker, but its email stays visible + findable ---
    check("inv-dead" not in facet_inv, "graveyard investor excluded from the facet dropdown")
    check("e6" in ids(res), "graveyard investor's email still shows in the unfiltered list (audit completeness)")
    e6 = next(e for e in res["emails"] if e["id"] == "e6")
    check(e6["investors"] == [{"id": "inv-dead", "name": "Dead Deal LP"}], "graveyard email still shows its investor chip")
    check(ids(_db.query_email_activity(conn, investor_id="inv-dead")) == ["e6"],
          "explicit investor_id filter still works for a graveyard investor")
    check(ids(_db.query_email_activity(conn, search="deaddeal")) == ["e6"],
          "graveyard email remains findable by free-text search")

    # --- truncation ---
    tr = _db.query_email_activity(conn, limit=2)
    check(tr["count"] == 2 and tr["truncated"] is True, "limit=2 -> truncated")

    conn.close()

    # --- route enforces admin server-side ---
    test_route_admin_only()

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


def test_route_admin_only():
    try:
        from email_integration import routes
    except Exception as e:  # pragma: no cover - optional deps missing in some dev envs
        print(f"  SKIP route admin test (routes import failed: {e})")
        return

    class FakeHandler:
        def __init__(self, user):
            self._user = user
            self.json = None
            self.err = None
            self.code = None

        def get_user(self):
            return self._user

        def get_query_params(self):
            return {}

        def send_json(self, obj):
            self.json = obj

        def send_error_json(self, msg, code):
            self.err = msg
            self.code = code

    h = FakeHandler(None)
    routes._h_activity(h)
    check(h.code == 401 and h.json is None, "route: no user -> 401")

    h = FakeHandler({"role": "member", "user_id": "u1"})
    routes._h_activity(h)
    check(h.code == 403 and h.json is None, "route: member -> 403 (admin enforced server-side)")


if __name__ == "__main__":
    main()