Email not sent on password resetting

[Vdauphin]

Hello, here again!

Info

I am running Gramps Web in a docker after following this guide https://gramps-project.github.io/web/Deployment/#step-1-docker-configuration. I am using this .yml to make it available as a One Click app in CapRover

Issue

When asking for password reset, no email are sent to my Outlook mail box (SMTP, STARTTLS) even it is saying yes:

Any idea if the issue is coming from a wrong docker setup or it could be just me setting up badly my mail information?

Logs

grampscelery

2023-04-22T20:32:10.720244961Z worker: Warm shutdown (MainProcess)
2023-04-22T20:32:24.816660710Z INFO  [alembic.runtime.migration] Context impl SQLiteImpl.
2023-04-22T20:32:24.816707507Z INFO  [alembic.runtime.migration] Will assume non-transactional DDL.
2023-04-22T20:32:27.448039161Z /usr/local/lib/python3.9/dist-packages/celery/platforms.py:840: SecurityWarning: You're running the worker with superuser privileges: this is
2023-04-22T20:32:27.448065451Z absolutely not recommended!
2023-04-22T20:32:27.448071558Z 
2023-04-22T20:32:27.448075527Z Please specify a different user using the --uid option.
2023-04-22T20:32:27.448079522Z 
2023-04-22T20:32:27.448083378Z User information: uid=0 euid=0 gid=0 egid=0
2023-04-22T20:32:27.448087281Z 
2023-04-22T20:32:27.448091058Z   warnings.warn(SecurityWarning(ROOT_DISCOURAGED.format(
2023-04-22T20:32:27.516141659Z  
2023-04-22T20:32:27.516171197Z  -------------- celery@ba32cc2f5f2a v5.2.7 (dawn-chorus)
2023-04-22T20:32:27.516176431Z --- ***** ----- 
2023-04-22T20:32:27.516180428Z -- ******* ---- Linux-5.4.0-144-generic-x86_64-with-glibc2.31 2023-04-22 20:32:27
2023-04-22T20:32:27.516184417Z - *** --- * --- 
2023-04-22T20:32:27.516188091Z - ** ---------- [config]
2023-04-22T20:32:27.516195190Z - ** ---------- .> app:         default:0x7f8f0bba05e0 (.default.Loader)
2023-04-22T20:32:27.516199811Z - ** ---------- .> transport:   redis://srv-captain--notrearbre-redis:6379/0
2023-04-22T20:32:27.516204369Z - ** ---------- .> results:     redis://srv-captain--notrearbre-redis:6379/0
2023-04-22T20:32:27.516208315Z - *** --- * --- .> concurrency: 8 (prefork)
2023-04-22T20:32:27.516212238Z -- ******* ---- .> task events: OFF (enable -E to monitor tasks in this worker)
2023-04-22T20:32:27.516216148Z --- ***** ----- 
2023-04-22T20:32:27.516219776Z  -------------- [queues]
2023-04-22T20:32:27.516223467Z                 .> celery           exchange=celery(direct) key=celery
2023-04-22T20:32:27.516227464Z                 
2023-04-22T20:32:27.516231128Z 
2023-04-22T20:32:27.516234687Z [tasks]
2023-04-22T20:32:27.516238255Z   . gramps_webapi.api.tasks.export_db
2023-04-22T20:32:27.516241899Z   . gramps_webapi.api.tasks.import_file
2023-04-22T20:32:27.516245553Z   . gramps_webapi.api.tasks.search_reindex_full
2023-04-22T20:32:27.516249307Z   . gramps_webapi.api.tasks.search_reindex_incremental
2023-04-22T20:32:27.516253057Z   . gramps_webapi.api.tasks.send_email_confirm_email
2023-04-22T20:32:27.516256794Z   . gramps_webapi.api.tasks.send_email_new_user
2023-04-22T20:32:27.516260506Z   . gramps_webapi.api.tasks.send_email_reset_password
2023-04-22T20:32:27.516264246Z 
2023-04-22T20:32:28.127445539Z [2023-04-22 20:32:28,126: INFO/MainProcess] Connected to redis://srv-captain--notrearbre-redis:6379/0
2023-04-22T20:32:28.129811456Z [2023-04-22 20:32:28,129: INFO/MainProcess] mingle: searching for neighbors
2023-04-22T20:32:29.140781053Z [2023-04-22 20:32:29,140: INFO/MainProcess] mingle: all alone
2023-04-22T20:32:29.158714721Z [2023-04-22 20:32:29,158: INFO/MainProcess] celery@ba32cc2f5f2a ready.
2023-04-22T20:34:33.120185446Z [2023-04-22 20:34:33,119: INFO/MainProcess] Task gramps_webapi.api.tasks.send_email_reset_password[0abd79ad-75c1-4b4b-ab1c-b7b98e5eb1a6] received
2023-04-22T20:34:33.195347917Z [2023-04-22 20:34:33,194: ERROR/ForkPoolWorker-8] Error while trying to send e-mail.
2023-04-22T20:34:33.203277828Z [2023-04-22 20:34:33,202: ERROR/ForkPoolWorker-8] Task gramps_webapi.api.tasks.send_email_reset_password[0abd79ad-75c1-4b4b-ab1c-b7b98e5eb1a6] raised unexpected: ValueError('Error while trying to send e-mail.')
2023-04-22T20:34:33.203308911Z Traceback (most recent call last):
2023-04-22T20:34:33.203316822Z   File "/usr/local/lib/python3.9/dist-packages/gramps_webapi/api/util.py", line 243, in send_email
2023-04-22T20:34:33.203324443Z     smtp = smtplib.SMTP_SSL(host=host, port=port, timeout=10)
2023-04-22T20:34:33.203331261Z   File "/usr/lib/python3.9/smtplib.py", line 1034, in __init__
2023-04-22T20:34:33.203338599Z     SMTP.__init__(self, host, port, local_hostname, timeout,
2023-04-22T20:34:33.203345138Z   File "/usr/lib/python3.9/smtplib.py", line 253, in __init__
2023-04-22T20:34:33.203351815Z     (code, msg) = self.connect(host, port)
2023-04-22T20:34:33.203358161Z   File "/usr/lib/python3.9/smtplib.py", line 339, in connect
2023-04-22T20:34:33.203364727Z     self.sock = self._get_socket(host, port, self.timeout)
2023-04-22T20:34:33.203371161Z   File "/usr/lib/python3.9/smtplib.py", line 1041, in _get_socket
2023-04-22T20:34:33.203377800Z     new_socket = self.context.wrap_socket(new_socket,
2023-04-22T20:34:33.203384328Z   File "/usr/lib/python3.9/ssl.py", line 500, in wrap_socket
2023-04-22T20:34:33.203390883Z     return self.sslsocket_class._create(
2023-04-22T20:34:33.203397137Z   File "/usr/lib/python3.9/ssl.py", line 1040, in _create
2023-04-22T20:34:33.203403743Z     self.do_handshake()
2023-04-22T20:34:33.203409999Z   File "/usr/lib/python3.9/ssl.py", line 1309, in do_handshake
2023-04-22T20:34:33.203416582Z     self._sslobj.do_handshake()
2023-04-22T20:34:33.203422887Z ssl.SSLError: [SSL: WRONG_VERSION_NUMBER] wrong version number (_ssl.c:1123)
2023-04-22T20:34:33.203429462Z 
2023-04-22T20:34:33.203435605Z During handling of the above exception, another exception occurred:
2023-04-22T20:34:33.203442111Z 
2023-04-22T20:34:33.203448198Z Traceback (most recent call last):
2023-04-22T20:34:33.203454410Z   File "/usr/local/lib/python3.9/dist-packages/celery/app/trace.py", line 451, in trace_task
2023-04-22T20:34:33.203461156Z     R = retval = fun(*args, **kwargs)
2023-04-22T20:34:33.203467374Z   File "/usr/local/lib/python3.9/dist-packages/gramps_webapi/util/celery.py", line 20, in __call__
2023-04-22T20:34:33.203493168Z     return self.run(*args, **kwargs)
2023-04-22T20:34:33.203500120Z   File "/usr/local/lib/python3.9/dist-packages/gramps_webapi/api/tasks.py", line 62, in send_email_reset_password
2023-04-22T20:34:33.203506657Z     send_email(subject=subject, body=body, to=[email])
2023-04-22T20:34:33.203512605Z   File "/usr/local/lib/python3.9/dist-packages/gramps_webapi/api/util.py", line 258, in send_email
2023-04-22T20:34:33.203518911Z     raise ValueError("Error while trying to send e-mail.")
2023-04-22T20:34:33.203525010Z ValueError: Error while trying to send e-mail.

[DavidMStraub]

Hmm, when using celery the success message is actually misleading because it just means that the task to send the e-mail has been added to the queue...

Not sure what is going wrong. Can you please try the following and see if you can reproduce the issue?

import smtplib
from email.message import EmailMessage
from email.utils import make_msgid


msg = EmailMessage()
msg.set_content("Hello world.")
msg["Subject"] = "Gramps Web test"
msg["From"] = "..."
msg["To"] = "..."
msg["Message-ID"] = make_msgid()

host = "..."
port = 465
user = "..."
password = "..."
smtp = smtplib.SMTP_SSL(host=host, port=port, timeout=10)
smtp.login(user, password)
smtp.send_message(msg)
smtp.quit()

[Vdauphin]

Thank you for the code, it help me a lot
Apparently it is not working because Outlook do not support SSL but STARTTLS
See https://support.microsoft.com/fr-fr/office/param%C3%A8tres-pop-imap-et-smtp-8361e398-8af4-4e97-b147-6c6c4ac95353
I tested your code snippset with SFR provider which does support SSL and it works