import random from email.message import EmailMessage from typing import List import pytest from aiosmtpd.smtp import Envelope import email_handler from app.config import BOUNCE_EMAIL, EMAIL_DOMAIN, ALERT_DMARC_FAILED_REPLY_PHASE from app.db import Session from app.email import headers, status from app.models import ( User, Alias, AuthorizedAddress, IgnoredEmail, EmailLog, Notification, Contact, SentAlert, ) from email_handler import ( get_mailbox_from_mail_from, should_ignore, is_automatic_out_of_office, ) from tests.utils import load_eml_file, create_random_user def test_get_mailbox_from_mail_from(flask_client): user = User.create( email="a@b.c", password="password", name="Test User", activated=True, commit=True, ) alias = Alias.create( user_id=user.id, email="first@d1.test", mailbox_id=user.default_mailbox_id, commit=True, ) mb = get_mailbox_from_mail_from("a@b.c", alias) assert mb.email == "a@b.c" mb = get_mailbox_from_mail_from("unauthorized@gmail.com", alias) assert mb is None # authorized address AuthorizedAddress.create( user_id=user.id, mailbox_id=user.default_mailbox_id, email="unauthorized@gmail.com", commit=True, ) mb = get_mailbox_from_mail_from("unauthorized@gmail.com", alias) assert mb.email == "a@b.c" def test_should_ignore(flask_client): assert should_ignore("mail_from", []) is False assert not should_ignore("mail_from", ["rcpt_to"]) IgnoredEmail.create(mail_from="mail_from", rcpt_to="rcpt_to", commit=True) assert should_ignore("mail_from", ["rcpt_to"]) def test_is_automatic_out_of_office(): msg = EmailMessage() assert not is_automatic_out_of_office(msg) msg[headers.AUTO_SUBMITTED] = "auto-replied" assert is_automatic_out_of_office(msg) del msg[headers.AUTO_SUBMITTED] assert not is_automatic_out_of_office(msg) msg[headers.AUTO_SUBMITTED] = "auto-generated" assert is_automatic_out_of_office(msg) def test_dmarc_forward_quarantine(flask_client): user = create_random_user() alias = Alias.create_new_random(user) msg = load_eml_file("dmarc_quarantine.eml", {"alias_email": alias.email}) envelope = Envelope() envelope.mail_from = msg["from"] envelope.rcpt_tos = [msg["to"]] result = email_handler.handle(envelope, msg) assert result == status.E215 email_logs = ( EmailLog.filter_by(user_id=user.id, alias_id=alias.id) .order_by(EmailLog.id.desc()) .all() ) assert len(email_logs) == 1 email_log = email_logs[0] assert email_log.blocked assert email_log.refused_email_id notifications = Notification.filter_by(user_id=user.id).all() assert len(notifications) == 1 assert f"{alias.email} has a new mail in quarantine" == notifications[0].title def test_gmail_dmarc_softfail(flask_client): user = create_random_user() alias = Alias.create_new_random(user) msg = load_eml_file("dmarc_gmail_softfail.eml", {"alias_email": alias.email}) envelope = Envelope() envelope.mail_from = msg["from"] envelope.rcpt_tos = [msg["to"]] result = email_handler.handle(envelope, msg) assert result == status.E200 payload = msg.get_payload() assert payload.find("failed anti-phishing checks") > -1 def test_prevent_5xx_from_spf(flask_client): user = create_random_user() alias = Alias.create_new_random(user) msg = load_eml_file( "5xx_overwrite_spf.eml", {"alias_email": alias.email, "spf_result": "R_SPF_FAIL"}, ) envelope = Envelope() envelope.mail_from = BOUNCE_EMAIL.format(999999999999999999) envelope.rcpt_tos = [msg["to"]] result = email_handler.MailHandler()._handle(envelope, msg) assert result == status.E216 def test_preserve_5xx_with_valid_spf(flask_client): user = create_random_user() alias = Alias.create_new_random(user) msg = load_eml_file( "5xx_overwrite_spf.eml", {"alias_email": alias.email, "spf_result": "R_SPF_ALLOW"}, ) envelope = Envelope() envelope.mail_from = BOUNCE_EMAIL.format(999999999999999999) envelope.rcpt_tos = [msg["to"]] result = email_handler.MailHandler()._handle(envelope, msg) assert result == status.E512 def test_preserve_5xx_with_no_header(flask_client): user = create_random_user() alias = Alias.create_new_random(user) msg = load_eml_file( "no_spamd_header.eml", {"alias_email": alias.email}, ) envelope = Envelope() envelope.mail_from = BOUNCE_EMAIL.format(999999999999999999) envelope.rcpt_tos = [msg["to"]] result = email_handler.MailHandler()._handle(envelope, msg) assert result == status.E512 def generate_dmarc_result() -> List: return ["DMARC_POLICY_QUARANTINE", "DMARC_POLICY_REJECT", "DMARC_POLICY_SOFTFAIL"] @pytest.mark.parametrize("dmarc_result", generate_dmarc_result()) def test_dmarc_reply_quarantine(flask_client, dmarc_result): user = create_random_user() alias = Alias.create_new_random(user) Session.commit() contact = Contact.create( user_id=alias.user_id, alias_id=alias.id, website_email="random-{}@nowhere.net".format(int(random.random())), name="Name {}".format(int(random.random())), reply_email="random-{}@{}".format(random.random(), EMAIL_DOMAIN), ) Session.commit() msg = load_eml_file( "dmarc_reply_check.eml", { "alias_email": alias.email, "contact_email": contact.reply_email, "dmarc_result": dmarc_result, }, ) envelope = Envelope() envelope.mail_from = msg["from"] envelope.rcpt_tos = [msg["to"]] result = email_handler.handle(envelope, msg) assert result == status.E215 alerts = SentAlert.filter_by( user_id=user.id, alert_type=ALERT_DMARC_FAILED_REPLY_PHASE ).all() assert len(alerts) == 1