Send out emails with links to extend an account's validity period

changelog.d/5047.feature

@@ -0,0 +1 @@
+Add time-based account expiration.

docs/sample_config.yaml

@@ -643,11 +643,31 @@ uploads_path: "DATADIR/uploads"
 #
 #enable_registration: false
 
-# Optional account validity parameter. This allows for, e.g., accounts to
-# be denied any request after a given period.
+# Optional account validity configuration. This allows for accounts to be denied
+# any request after a given period.
+#
+# ``enabled`` defines whether the account validity feature is enabled. Defaults
+# to False.
+#
+# ``period`` allows setting the period after which an account is valid
+# after its registration. When renewing the account, its validity period
+# will be extended by this amount of time. This parameter is required when using
+# the account validity feature.
+#
+# ``renew_at`` is the amount of time before an account's expiry date at which
+# Synapse will send an email to the account's email address with a renewal link.
+# This needs the ``email`` and ``public_baseurl`` configuration sections to be
+# filled.
+#
+# ``renew_email_subject`` is the subject of the email sent out with the renewal
+# link. ``%(app)s`` can be used as a placeholder for the ``app_name`` parameter
+# from the ``email`` section.
 #
 #account_validity:
+#  enabled: True
 #  period: 6w
+#  renew_at: 1w
+#  renew_email_subject: "Renew your %(app)s account"
 
 # The user must provide all of the below types of 3PID when registering.
 #
@@ -890,7 +910,7 @@ password_config:
 
 
 
-# Enable sending emails for notification events
+# Enable sending emails for notification events or expiry notices
 # Defining a custom URL for Riot is only needed if email notifications
 # should contain links to a self-hosted installation of Riot; when set
 # the "app_name" setting is ignored.
@@ -912,6 +932,9 @@ password_config:
 #   #template_dir: res/templates
 #   notif_template_html: notif_mail.html
 #   notif_template_text: notif_mail.txt
+#   # Templates for account expiry notices.
+#   expiry_template_html: notice_expiry.html
+#   expiry_template_text: notice_expiry.txt
 #   notif_for_new_users: True
 #   riot_base_url: "http://localhost/riot"
 

synapse/api/auth.py

@@ -230,8 +230,9 @@ class Auth(object):
 
             # Deny the request if the user account has expired.
             if self._account_validity.enabled:
-                expiration_ts = yield self.store.get_expiration_ts_for_user(user)
-                if self.clock.time_msec() >= expiration_ts:
+                user_id = user.to_string()
+                expiration_ts = yield self.store.get_expiration_ts_for_user(user_id)
+                if expiration_ts and self.clock.time_msec() >= expiration_ts:
                     raise AuthError(
                         403,
                         "User account has expired",

synapse/config/emailconfig.py

@@ -71,6 +71,8 @@ class EmailConfig(Config):
             self.email_notif_from = email_config["notif_from"]
             self.email_notif_template_html = email_config["notif_template_html"]
             self.email_notif_template_text = email_config["notif_template_text"]
+            self.email_expiry_template_html = email_config["expiry_template_html"]
+            self.email_expiry_template_text = email_config["expiry_template_text"]
 
             template_dir = email_config.get("template_dir")
             # we need an absolute path, because we change directory after starting (and
@@ -120,7 +122,7 @@ class EmailConfig(Config):
 
     def default_config(self, config_dir_path, server_name, **kwargs):
         return """
-        # Enable sending emails for notification events
+        # Enable sending emails for notification events or expiry notices
         # Defining a custom URL for Riot is only needed if email notifications
         # should contain links to a self-hosted installation of Riot; when set
         # the "app_name" setting is ignored.
@@ -142,6 +144,9 @@ class EmailConfig(Config):
         #   #template_dir: res/templates
         #   notif_template_html: notif_mail.html
         #   notif_template_text: notif_mail.txt
+        #   # Templates for account expiry notices.
+        #   expiry_template_html: notice_expiry.html
+        #   expiry_template_text: notice_expiry.txt
         #   notif_for_new_users: True
         #   riot_base_url: "http://localhost/riot"
         """

synapse/config/registration.py

@@ -21,12 +21,26 @@ from synapse.util.stringutils import random_string_with_symbols
 
 
 class AccountValidityConfig(Config):
-    def __init__(self, config):
-        self.enabled = (len(config) > 0)
+    def __init__(self, config, synapse_config):
+        self.enabled = config.get("enabled", False)
+        self.renew_by_email_enabled = ("renew_at" in config)
 
-        period = config.get("period", None)
-        if period:
-            self.period = self.parse_duration(period)
+        if self.enabled:
+            if "period" in config:
+                self.period = self.parse_duration(config["period"])
+            else:
+                raise ConfigError("'period' is required when using account validity")
+
+            if "renew_at" in config:
+                self.renew_at = self.parse_duration(config["renew_at"])
+
+            if "renew_email_subject" in config:
+                self.renew_email_subject = config["renew_email_subject"]
+            else:
+                self.renew_email_subject = "Renew your %(app)s account"
+
+        if self.renew_by_email_enabled and "public_baseurl" not in synapse_config:
+            raise ConfigError("Can't send renewal emails without 'public_baseurl'")
 
 
 class RegistrationConfig(Config):
@@ -40,7 +54,9 @@ class RegistrationConfig(Config):
                 strtobool(str(config["disable_registration"]))
             )
 
-        self.account_validity = AccountValidityConfig(config.get("account_validity", {}))
+        self.account_validity = AccountValidityConfig(
+            config.get("account_validity", {}), config,
+        )
 
         self.registrations_require_3pid = config.get("registrations_require_3pid", [])
         self.allowed_local_3pids = config.get("allowed_local_3pids", [])
@@ -86,11 +102,31 @@ class RegistrationConfig(Config):
         #
         #enable_registration: false
 
-        # Optional account validity parameter. This allows for, e.g., accounts to
-        # be denied any request after a given period.
+        # Optional account validity configuration. This allows for accounts to be denied
+        # any request after a given period.
+        #
+        # ``enabled`` defines whether the account validity feature is enabled. Defaults
+        # to False.
+        #
+        # ``period`` allows setting the period after which an account is valid
+        # after its registration. When renewing the account, its validity period
+        # will be extended by this amount of time. This parameter is required when using
+        # the account validity feature.
+        #
+        # ``renew_at`` is the amount of time before an account's expiry date at which
+        # Synapse will send an email to the account's email address with a renewal link.
+        # This needs the ``email`` and ``public_baseurl`` configuration sections to be
+        # filled.
+        #
+        # ``renew_email_subject`` is the subject of the email sent out with the renewal
+        # link. ``%%(app)s`` can be used as a placeholder for the ``app_name`` parameter
+        # from the ``email`` section.
         #
         #account_validity:
+        #  enabled: True
         #  period: 6w
+        #  renew_at: 1w
+        #  renew_email_subject: "Renew your %%(app)s account"
 
         # The user must provide all of the below types of 3PID when registering.
         #

synapse/handlers/account_validity.py

@@ -0,0 +1,228 @@
+# -*- coding: utf-8 -*-
+# Copyright 2019 New Vector Ltd
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+import email.mime.multipart
+import email.utils
+import logging
+from email.mime.multipart import MIMEMultipart
+from email.mime.text import MIMEText
+
+from twisted.internet import defer
+
+from synapse.api.errors import StoreError
+from synapse.types import UserID
+from synapse.util import stringutils
+from synapse.util.logcontext import make_deferred_yieldable
+
+try:
+    from synapse.push.mailer import load_jinja2_templates
+except ImportError:
+    load_jinja2_templates = None
+
+logger = logging.getLogger(__name__)
+
+
+class AccountValidityHandler(object):
+    def __init__(self, hs):
+        self.hs = hs
+        self.store = self.hs.get_datastore()
+        self.sendmail = self.hs.get_sendmail()
+        self.clock = self.hs.get_clock()
+
+        self._account_validity = self.hs.config.account_validity
+
+        if self._account_validity.renew_by_email_enabled and load_jinja2_templates:
+            # Don't do email-specific configuration if renewal by email is disabled.
+            try:
+                app_name = self.hs.config.email_app_name
+
+                self._subject = self._account_validity.renew_email_subject % {
+                    "app": app_name,
+                }
+
+                self._from_string = self.hs.config.email_notif_from % {
+                    "app": app_name,
+                }
+            except Exception:
+                # If substitution failed, fall back to the bare strings.
+                self._subject = self._account_validity.renew_email_subject
+                self._from_string = self.hs.config.email_notif_from
+
+            self._raw_from = email.utils.parseaddr(self._from_string)[1]
+
+            self._template_html, self._template_text = load_jinja2_templates(
+                config=self.hs.config,
+                template_html_name=self.hs.config.email_expiry_template_html,
+                template_text_name=self.hs.config.email_expiry_template_text,
+            )
+
+            # Check the renewal emails to send and send them every 30min.
+            self.clock.looping_call(
+                self.send_renewal_emails,
+                30 * 60 * 1000,
+            )
+
+    @defer.inlineCallbacks
+    def send_renewal_emails(self):
+        """Gets the list of users whose account is expiring in the amount of time
+        configured in the ``renew_at`` parameter from the ``account_validity``
+        configuration, and sends renewal emails to all of these users as long as they
+        have an email 3PID attached to their account.
+        """
+        expiring_users = yield self.store.get_users_expiring_soon()
+
+        if expiring_users:
+            for user in expiring_users:
+                yield self._send_renewal_email(
+                    user_id=user["user_id"],
+                    expiration_ts=user["expiration_ts_ms"],
+                )
+
+    @defer.inlineCallbacks
+    def _send_renewal_email(self, user_id, expiration_ts):
+        """Sends out a renewal email to every email address attached to the given user
+        with a unique link allowing them to renew their account.
+
+        Args:
+            user_id (str): ID of the user to send email(s) to.
+            expiration_ts (int): Timestamp in milliseconds for the expiration date of
+                this user's account (used in the email templates).
+        """
+        addresses = yield self._get_email_addresses_for_user(user_id)
+
+        # Stop right here if the user doesn't have at least one email address.
+        # In this case, they will have to ask their server admin to renew their
+        # account manually.
+        if not addresses:
+            return
+
+        try:
+            user_display_name = yield self.store.get_profile_displayname(
+                UserID.from_string(user_id).localpart
+            )
+            if user_display_name is None:
+                user_display_name = user_id
+        except StoreError:
+            user_display_name = user_id
+
+        renewal_token = yield self._get_renewal_token(user_id)
+        url = "%s_matrix/client/unstable/account_validity/renew?token=%s" % (
+            self.hs.config.public_baseurl,
+            renewal_token,
+        )
+
+        template_vars = {
+            "display_name": user_display_name,
+            "expiration_ts": expiration_ts,
+            "url": url,
+        }
+
+        html_text = self._template_html.render(**template_vars)
+        html_part = MIMEText(html_text, "html", "utf8")
+
+        plain_text = self._template_text.render(**template_vars)
+        text_part = MIMEText(plain_text, "plain", "utf8")
+
+        for address in addresses:
+            raw_to = email.utils.parseaddr(address)[1]
+
+            multipart_msg = MIMEMultipart('alternative')
+            multipart_msg['Subject'] = self._subject
+            multipart_msg['From'] = self._from_string
+            multipart_msg['To'] = address
+            multipart_msg['Date'] = email.utils.formatdate()
+            multipart_msg['Message-ID'] = email.utils.make_msgid()
+            multipart_msg.attach(text_part)
+            multipart_msg.attach(html_part)
+
+            logger.info("Sending renewal email to %s", address)
+
+            yield make_deferred_yieldable(self.sendmail(
+                self.hs.config.email_smtp_host,
+                self._raw_from, raw_to, multipart_msg.as_string().encode('utf8'),
+                reactor=self.hs.get_reactor(),
+                port=self.hs.config.email_smtp_port,
+                requireAuthentication=self.hs.config.email_smtp_user is not None,
+                username=self.hs.config.email_smtp_user,
+                password=self.hs.config.email_smtp_pass,
+                requireTransportSecurity=self.hs.config.require_transport_security
+            ))
+
+        yield self.store.set_renewal_mail_status(
+            user_id=user_id,
+            email_sent=True,
+        )
+
+    @defer.inlineCallbacks
+    def _get_email_addresses_for_user(self, user_id):
+        """Retrieve the list of email addresses attached to a user's account.
+
+        Args:
+            user_id (str): ID of the user to lookup email addresses for.
+
+        Returns:
+            defer.Deferred[list[str]]: Email addresses for this account.
+        """
+        threepids = yield self.store.user_get_threepids(user_id)
+
+        addresses = []
+        for threepid in threepids:
+            if threepid["medium"] == "email":
+                addresses.append(threepid["address"])
+
+        defer.returnValue(addresses)
+
+    @defer.inlineCallbacks
+    def _get_renewal_token(self, user_id):
+        """Generates a 32-byte long random string that will be inserted into the
+        user's renewal email's unique link, then saves it into the database.
+
+        Args:
+            user_id (str): ID of the user to generate a string for.
+
+        Returns:
+            defer.Deferred[str]: The generated string.
+
+        Raises:
+            StoreError(500): Couldn't generate a unique string after 5 attempts.
+        """
+        attempts = 0
+        while attempts < 5:
+            try:
+                renewal_token = stringutils.random_string(32)
+                yield self.store.set_renewal_token_for_user(user_id, renewal_token)
+                defer.returnValue(renewal_token)
+            except StoreError:
+                attempts += 1
+        raise StoreError(500, "Couldn't generate a unique string as refresh string.")
+
+    @defer.inlineCallbacks
+    def renew_account(self, renewal_token):
+        """Renews the account attached to a given renewal token by pushing back the
+        expiration date by the current validity period in the server's configuration.
+
+        Args:
+            renewal_token (str): Token sent with the renewal request.
+        """
+        user_id = yield self.store.get_user_from_renewal_token(renewal_token)
+
+        logger.debug("Renewing an account for user %s", user_id)
+
+        new_expiration_date = self.clock.time_msec() + self._account_validity.period
+
+        yield self.store.renew_account_for_user(
+            user_id=user_id,
+            new_expiration_ts=new_expiration_date,
+        )

synapse/push/mailer.py

@@ -521,11 +521,11 @@ def format_ts_filter(value, format):
     return time.strftime(format, time.localtime(value / 1000))
 
 
-def load_jinja2_templates(config):
+def load_jinja2_templates(config, template_html_name, template_text_name):
     """Load the jinja2 email templates from disk
 
     Returns:
-        (notif_template_html, notif_template_text)
+        (template_html, template_text)
     """
     logger.info("loading email templates from '%s'", config.email_template_dir)
     loader = jinja2.FileSystemLoader(config.email_template_dir)
@@ -533,14 +533,10 @@ def load_jinja2_templates(config):
     env.filters["format_ts"] = format_ts_filter
     env.filters["mxc_to_http"] = _create_mxc_to_http_filter(config)
 
-    notif_template_html = env.get_template(
-        config.email_notif_template_html
-    )
-    notif_template_text = env.get_template(
-        config.email_notif_template_text
-    )
+    template_html = env.get_template(template_html_name)
+    template_text = env.get_template(template_text_name)
 
-    return notif_template_html, notif_template_text
+    return template_html, template_text
 
 
 def _create_mxc_to_http_filter(config):

synapse/push/pusher.py

@@ -44,7 +44,11 @@ class PusherFactory(object):
         if hs.config.email_enable_notifs:
             self.mailers = {}  # app_name -> Mailer
 
-            templates = load_jinja2_templates(hs.config)
+            templates = load_jinja2_templates(
+                config=hs.config,
+                template_html_name=hs.config.email_notif_template_html,
+                template_text_name=hs.config.email_notif_template_text,
+            )
             self.notif_template_html, self.notif_template_text = templates
 
             self.pusher_types["email"] = self._create_email_pusher

synapse/res/templates/mail-expiry.css

@@ -0,0 +1,4 @@
+.noticetext {
+    margin-top: 10px;
+    margin-bottom: 10px;
+}

synapse/res/templates/notice_expiry.html

@@ -0,0 +1,43 @@
+<!doctype html>
+<html lang="en">
+    <head>
+        <style type="text/css">
+            {% include 'mail.css' without context %}
+            {% include "mail-%s.css" % app_name ignore missing without context %}
+            {% include 'mail-expiry.css' without context %}
+        </style>
+    </head>
+    <body>
+        <table id="page">
+            <tr>
+                <td> </td>
+                <td id="inner">
+                    <table class="header">
+                        <tr>
+                            <td>
+                                <div class="salutation">Hi {{ display_name }},</div>
+                            </td>
+                            <td class="logo">
+                                {% if app_name == "Riot" %}
+                                    <img src="http://riot.im/img/external/riot-logo-email.png" width="83" height="83" alt="[Riot]"/>
+                                {% elif app_name == "Vector" %}
+                                    <img src="http://matrix.org/img/vector-logo-email.png" width="64" height="83" alt="[Vector]"/>
+                                {% else %}
+                                    <img src="http://matrix.org/img/matrix-120x51.png" width="120" height="51" alt="[matrix]"/>
+                                {% endif %}
+                            </td>
+                        </tr>
+                        <tr>
+                          <td colspan="2">
+                            <div class="noticetext">Your account will expire on {{ expiration_ts|format_ts("%d-%m-%Y") }}. This means that you will lose access to your account after this date.</div>
+                            <div class="noticetext">To extend the validity of your account, please click on the link bellow (or copy and paste it into a new browser tab):</div>
+                            <div class="noticetext"><a href="{{ url }}">{{ url }}</a></div>
+                          </td>
+                        </tr>
+                    </table>
+                </td>
+                <td> </td>
+            </tr>
+        </table>
+    </body>
+</html>

synapse/res/templates/notice_expiry.txt

@@ -0,0 +1,7 @@
+Hi {{ display_name }},
+
+Your account will expire on {{ expiration_ts|format_ts("%d-%m-%Y") }}. This means that you will lose access to your account after this date.
+
+To extend the validity of your account, please click on the link bellow (or copy and paste it to a new browser tab):
+
+{{ url }}

synapse/rest/__init__.py

@@ -33,6 +33,7 @@ from synapse.rest.client.v1 import (
 from synapse.rest.client.v2_alpha import (
     account,
     account_data,
+    account_validity,
     auth,
     capabilities,
     devices,
@@ -109,3 +110,4 @@ class ClientRestResource(JsonResource):
         groups.register_servlets(hs, client_resource)
         room_upgrade_rest_servlet.register_servlets(hs, client_resource)
         capabilities.register_servlets(hs, client_resource)
+        account_validity.register_servlets(hs, client_resource)

synapse/rest/client/v2_alpha/account_validity.py

@@ -0,0 +1,62 @@
+# -*- coding: utf-8 -*-
+# Copyright 2019 New Vector Ltd
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+import logging
+
+from twisted.internet import defer
+
+from synapse.api.errors import SynapseError
+from synapse.http.server import finish_request
+from synapse.http.servlet import RestServlet
+
+from ._base import client_v2_patterns
+
+logger = logging.getLogger(__name__)
+
+
+class AccountValidityRenewServlet(RestServlet):
+    PATTERNS = client_v2_patterns("/account_validity/renew$")
+    SUCCESS_HTML = b"<html><body>Your account has been successfully renewed.</body><html>"
+
+    def __init__(self, hs):
+        """
+        Args:
+            hs (synapse.server.HomeServer): server
+        """
+        super(AccountValidityRenewServlet, self).__init__()
+
+        self.hs = hs
+        self.account_activity_handler = hs.get_account_validity_handler()
+
+    @defer.inlineCallbacks
+    def on_GET(self, request):
+        if b"token" not in request.args:
+            raise SynapseError(400, "Missing renewal token")
+        renewal_token = request.args[b"token"][0]
+
+        yield self.account_activity_handler.renew_account(renewal_token.decode('utf8'))
+
+        request.setResponseCode(200)
+        request.setHeader(b"Content-Type", b"text/html; charset=utf-8")
+        request.setHeader(b"Content-Length", b"%d" % (
+            len(AccountValidityRenewServlet.SUCCESS_HTML),
+        ))
+        request.write(AccountValidityRenewServlet.SUCCESS_HTML)
+        finish_request(request)
+        defer.returnValue(None)
+
+
+def register_servlets(hs, http_server):
+    AccountValidityRenewServlet(hs).register(http_server)

synapse/server.py

@@ -47,6 +47,7 @@ from synapse.federation.transport.client import TransportLayerClient
 from synapse.groups.attestations import GroupAttestationSigning, GroupAttestionRenewer
 from synapse.groups.groups_server import GroupsServerHandler
 from synapse.handlers import Handlers
+from synapse.handlers.account_validity import AccountValidityHandler
 from synapse.handlers.acme import AcmeHandler
 from synapse.handlers.appservice import ApplicationServicesHandler
 from synapse.handlers.auth import AuthHandler, MacaroonGenerator
@@ -183,6 +184,7 @@ class HomeServer(object):
         'room_context_handler',
         'sendmail',
         'registration_handler',
+        'account_validity_handler',
     ]
 
     REQUIRED_ON_MASTER_STARTUP = [
@@ -506,6 +508,9 @@ class HomeServer(object):
     def build_registration_handler(self):
         return RegistrationHandler(self)
 
+    def build_account_validity_handler(self):
+        return AccountValidityHandler(self)
+
     def remove_pusher(self, app_id, push_key, user_id):
         return self.get_pusherpool().remove_pusher(app_id, push_key, user_id)
 

synapse/storage/registration.py

@@ -32,6 +32,7 @@ class RegistrationWorkerStore(SQLBaseStore):
         super(RegistrationWorkerStore, self).__init__(db_conn, hs)
 
         self.config = hs.config
+        self.clock = hs.get_clock()
 
     @cached()
     def get_user_by_id(self, user_id):
@@ -87,25 +88,156 @@ class RegistrationWorkerStore(SQLBaseStore):
         )
 
     @cachedInlineCallbacks()
-    def get_expiration_ts_for_user(self, user):
+    def get_expiration_ts_for_user(self, user_id):
         """Get the expiration timestamp for the account bearing a given user ID.
 
         Args:
-            user (str): The ID of the user.
+            user_id (str): The ID of the user.
         Returns:
             defer.Deferred: None, if the account has no expiration timestamp,
-            otherwise int representation of the timestamp (as a number of
-            milliseconds since epoch).
+                otherwise int representation of the timestamp (as a number of
+                milliseconds since epoch).
         """
         res = yield self._simple_select_one_onecol(
             table="account_validity",
-            keyvalues={"user_id": user.to_string()},
+            keyvalues={"user_id": user_id},
             retcol="expiration_ts_ms",
             allow_none=True,
-            desc="get_expiration_date_for_user",
+            desc="get_expiration_ts_for_user",
         )
         defer.returnValue(res)
 
+    @defer.inlineCallbacks
+    def renew_account_for_user(self, user_id, new_expiration_ts):
+        """Updates the account validity table with a new timestamp for a given
+        user, removes the existing renewal token from this user, and unsets the
+        flag indicating that an email has been sent for renewing this account.
+
+        Args:
+            user_id (str): ID of the user whose account validity to renew.
+            new_expiration_ts: New expiration date, as a timestamp in milliseconds
+                since epoch.
+        """
+        def renew_account_for_user_txn(txn):
+            self._simple_update_txn(
+                txn=txn,
+                table="account_validity",
+                keyvalues={"user_id": user_id},
+                updatevalues={
+                    "expiration_ts_ms": new_expiration_ts,
+                    "email_sent": False,
+                    "renewal_token": None,
+                },
+            )
+            self._invalidate_cache_and_stream(
+                txn, self.get_expiration_ts_for_user, (user_id,),
+            )
+
+        yield self.runInteraction(
+            "renew_account_for_user",
+            renew_account_for_user_txn,
+        )
+
+    @defer.inlineCallbacks
+    def set_renewal_token_for_user(self, user_id, renewal_token):
+        """Defines a renewal token for a given user.
+
+        Args:
+            user_id (str): ID of the user to set the renewal token for.
+            renewal_token (str): Random unique string that will be used to renew the
+                user's account.
+
+        Raises:
+            StoreError: The provided token is already set for another user.
+        """
+        yield self._simple_update_one(
+            table="account_validity",
+            keyvalues={"user_id": user_id},
+            updatevalues={"renewal_token": renewal_token},
+            desc="set_renewal_token_for_user",
+        )
+
+    @defer.inlineCallbacks
+    def get_user_from_renewal_token(self, renewal_token):
+        """Get a user ID from a renewal token.
+
+        Args:
+            renewal_token (str): The renewal token to perform the lookup with.
+
+        Returns:
+            defer.Deferred[str]: The ID of the user to which the token belongs.
+        """
+        res = yield self._simple_select_one_onecol(
+            table="account_validity",
+            keyvalues={"renewal_token": renewal_token},
+            retcol="user_id",
+            desc="get_user_from_renewal_token",
+        )
+
+        defer.returnValue(res)
+
+    @defer.inlineCallbacks
+    def get_renewal_token_for_user(self, user_id):
+        """Get the renewal token associated with a given user ID.
+
+        Args:
+            user_id (str): The user ID to lookup a token for.
+
+        Returns:
+            defer.Deferred[str]: The renewal token associated with this user ID.
+        """
+        res = yield self._simple_select_one_onecol(
+            table="account_validity",
+            keyvalues={"user_id": user_id},
+            retcol="renewal_token",
+            desc="get_renewal_token_for_user",
+        )
+
+        defer.returnValue(res)
+
+    @defer.inlineCallbacks
+    def get_users_expiring_soon(self):
+        """Selects users whose account will expire in the [now, now + renew_at] time
+        window (see configuration for account_validity for information on what renew_at
+        refers to).
+
+        Returns:
+            Deferred: Resolves to a list[dict[user_id (str), expiration_ts_ms (int)]]
+        """
+        def select_users_txn(txn, now_ms, renew_at):
+            sql = (
+                "SELECT user_id, expiration_ts_ms FROM account_validity"
+                " WHERE email_sent = ? AND (expiration_ts_ms - ?) <= ?"
+            )
+            values = [False, now_ms, renew_at]
+            txn.execute(sql, values)
+            return self.cursor_to_dict(txn)
+
+        res = yield self.runInteraction(
+            "get_users_expiring_soon",
+            select_users_txn,
+            self.clock.time_msec(), self.config.account_validity.renew_at,
+        )
+
+        defer.returnValue(res)
+
+    @defer.inlineCallbacks
+    def set_renewal_mail_status(self, user_id, email_sent):
+        """Sets or unsets the flag that indicates whether a renewal email has been sent
+        to the user (and the user hasn't renewed their account yet).
+
+        Args:
+            user_id (str): ID of the user to set/unset the flag for.
+            email_sent (bool): Flag which indicates whether a renewal email has been sent
+                to this user.
+        """
+        yield self._simple_update_one(
+            table="account_validity",
+            keyvalues={"user_id": user_id},
+            updatevalues={"email_sent": email_sent},
+            desc="set_renewal_mail_status",
+        )
+
     @defer.inlineCallbacks
     def is_server_admin(self, user):
         res = yield self._simple_select_one_onecol(
@@ -508,22 +640,24 @@ class RegistrationStore(RegistrationWorkerStore,
                     }
                 )
 
-            if self._account_validity.enabled:
-                now_ms = self.clock.time_msec()
-                expiration_ts = now_ms + self._account_validity.period
-                self._simple_insert_txn(
-                    txn,
-                    "account_validity",
-                    values={
-                        "user_id": user_id,
-                        "expiration_ts_ms": expiration_ts,
-                    }
-                )
         except self.database_engine.module.IntegrityError:
             raise StoreError(
                 400, "User ID already taken.", errcode=Codes.USER_IN_USE
             )
 
+        if self._account_validity.enabled:
+            now_ms = self.clock.time_msec()
+            expiration_ts = now_ms + self._account_validity.period
+            self._simple_insert_txn(
+                txn,
+                "account_validity",
+                values={
+                    "user_id": user_id,
+                    "expiration_ts_ms": expiration_ts,
+                    "email_sent": False,
+                }
+            )
+
         if token:
             # it's possible for this to get a conflict, but only for a single user
             # since tokens are namespaced based on their user ID

synapse/storage/schema/delta/54/account_validity.sql

@@ -13,8 +13,15 @@
  * limitations under the License.
  */
 
+DROP TABLE IF EXISTS account_validity;
+
 -- Track what users are in public rooms.
 CREATE TABLE IF NOT EXISTS account_validity (
     user_id TEXT PRIMARY KEY,
-    expiration_ts_ms BIGINT NOT NULL
+    expiration_ts_ms BIGINT NOT NULL,
+    email_sent BOOLEAN NOT NULL,
+    renewal_token TEXT
 );
+
+CREATE INDEX account_validity_email_sent_idx ON account_validity(email_sent, expiration_ts_ms)
+CREATE UNIQUE INDEX account_validity_renewal_string_idx ON account_validity(renewal_token)

tests/rest/client/v2_alpha/test_register.py

@@ -1,14 +1,22 @@
 import datetime
 import json
+import os
+
+import pkg_resources
 
 from synapse.api.constants import LoginType
 from synapse.api.errors import Codes
 from synapse.appservice import ApplicationService
 from synapse.rest.client.v1 import admin, login
-from synapse.rest.client.v2_alpha import register, sync
+from synapse.rest.client.v2_alpha import account_validity, register, sync
 
 from tests import unittest
 
+try:
+    from synapse.push.mailer import load_jinja2_templates
+except ImportError:
+    load_jinja2_templates = None
+
 
 class RegisterRestServletTestCase(unittest.HomeserverTestCase):
 
@@ -197,6 +205,7 @@ class AccountValidityTestCase(unittest.HomeserverTestCase):
 
     def make_homeserver(self, reactor, clock):
         config = self.default_config()
+        # Test for account expiring after a week.
         config.enable_registration = True
         config.account_validity.enabled = True
         config.account_validity.period = 604800000  # Time in ms for 1 week
@@ -228,3 +237,92 @@ class AccountValidityTestCase(unittest.HomeserverTestCase):
         self.assertEquals(
             channel.json_body["errcode"], Codes.EXPIRED_ACCOUNT, channel.result,
         )
+
+
+class AccountValidityRenewalByEmailTestCase(unittest.HomeserverTestCase):
+
+    skip = "No Jinja installed" if not load_jinja2_templates else None
+    servlets = [
+        register.register_servlets,
+        admin.register_servlets,
+        login.register_servlets,
+        sync.register_servlets,
+        account_validity.register_servlets,
+    ]
+
+    def make_homeserver(self, reactor, clock):
+        config = self.default_config()
+        # Test for account expiring after a week and renewal emails being sent 2
+        # days before expiry.
+        config.enable_registration = True
+        config.account_validity.enabled = True
+        config.account_validity.renew_by_email_enabled = True
+        config.account_validity.period = 604800000  # Time in ms for 1 week
+        config.account_validity.renew_at = 172800000  # Time in ms for 2 days
+        config.account_validity.renew_email_subject = "Renew your account"
+
+        # Email config.
+        self.email_attempts = []
+
+        def sendmail(*args, **kwargs):
+            self.email_attempts.append((args, kwargs))
+            return
+
+        config.email_template_dir = os.path.abspath(
+            pkg_resources.resource_filename('synapse', 'res/templates')
+        )
+        config.email_expiry_template_html = "notice_expiry.html"
+        config.email_expiry_template_text = "notice_expiry.txt"
+        config.email_smtp_host = "127.0.0.1"
+        config.email_smtp_port = 20
+        config.require_transport_security = False
+        config.email_smtp_user = None
+        config.email_smtp_pass = None
+        config.email_notif_from = "test@example.com"
+
+        self.hs = self.setup_test_homeserver(config=config, sendmail=sendmail)
+
+        self.store = self.hs.get_datastore()
+
+        return self.hs
+
+    def test_renewal_email(self):
+        user_id = self.register_user("kermit", "monkey")
+        tok = self.login("kermit", "monkey")
+        # We need to manually add an email address otherwise the handler will do
+        # nothing.
+        now = self.hs.clock.time_msec()
+        self.get_success(self.store.user_add_threepid(
+            user_id=user_id, medium="email", address="kermit@example.com",
+            validated_at=now, added_at=now,
+        ))
+
+        # The specific endpoint doesn't matter, all we need is an authenticated
+        # endpoint.
+        request, channel = self.make_request(
+            b"GET", "/sync", access_token=tok,
+        )
+        self.render(request)
+        self.assertEquals(channel.result["code"], b"200", channel.result)
+
+        # Move 6 days forward. This should trigger a renewal email to be sent.
+        self.reactor.advance(datetime.timedelta(days=6).total_seconds())
+        self.assertEqual(len(self.email_attempts), 1)
+
+        # Retrieving the URL from the email is too much pain for now, so we
+        # retrieve the token from the DB.
+        renewal_token = self.get_success(self.store.get_renewal_token_for_user(user_id))
+        url = "/_matrix/client/unstable/account_validity/renew?token=%s" % renewal_token
+        request, channel = self.make_request(b"GET", url)
+        self.render(request)
+        self.assertEquals(channel.result["code"], b"200", channel.result)
+
+        # Move 3 days forward. If the renewal failed, every authed request with
+        # our access token should be denied from now, otherwise they should
+        # succeed.
+        self.reactor.advance(datetime.timedelta(days=3).total_seconds())
+        request, channel = self.make_request(
+            b"GET", "/sync", access_token=tok,
+        )
+        self.render(request)
+        self.assertEquals(channel.result["code"], b"200", channel.result)