[bug]: Emails are not sending for correct SMTP configurations

[ibtesamlatif2997]

Is there an existing issue for this?

• [X] I have searched the existing issues

Current behavior

Last week I have installed the self hosted docker version and successfully setup admin and workspace. From god mode I have setup the SMTP configurations and it's saving successfully, but still emails are not being sending. The same SMTP configurations are working from other platforms

I am using aws ses service for sending emails

The emails should be sent from plane, if the same configurations are working from other places

Steps to reproduce

1. Go to god mode
2. Setup smtp configurations
3. Invite people to workspace or signup from authentication code
4. The emails are not receving

Environment

Production

Browser

Google Chrome

Variant

Self-hosted

Version

stable

[ReggieMarr]

I have the same issue. I think it has to do with smtp verification not allowed (aka using an email service that requires 2FA).

I tried running the following:

➜  plane-app docker container ls
CONTAINER ID   IMAGE                             COMMAND                  CREATED          STATUS          PORTS                                   NAMES
2ab42776044b   makeplane/plane-proxy:stable      "/docker-entrypoint.…"   19 minutes ago   Up 19 minutes   0.0.0.0:8855->80/tcp, :::8855->80/tcp   plane-app-proxy-1
65be6cc2621f   makeplane/plane-space:stable      "docker-entrypoint.s…"   19 minutes ago   Up 19 minutes   3000/tcp                                plane-app-space-1
0fc0eacbe79d   makeplane/plane-frontend:stable   "docker-entrypoint.s…"   19 minutes ago   Up 19 minutes   3000/tcp                                plane-app-web-1
d0df019160f7   makeplane/plane-backend:stable    "./bin/beat"             19 minutes ago   Up 19 minutes   8000/tcp                                plane-app-beat-worker-1
ef70f5708846   makeplane/plane-backend:stable    "./bin/worker"           19 minutes ago   Up 19 minutes   8000/tcp                                plane-app-worker-1
6b2d0644acee   makeplane/plane-backend:stable    "./bin/takeoff"          19 minutes ago   Up 19 minutes   8000/tcp                                plane-app-api-1
acc2c69b7d45   redis:7.2.4-alpine                "docker-entrypoint.s…"   19 minutes ago   Up 19 minutes   6379/tcp                                plane-app-plane-redis-1
30e9568d330f   minio/minio                       "/usr/bin/docker-ent…"   19 minutes ago   Up 19 minutes   9000/tcp                                plane-app-plane-minio-1
8c49d3860cca   postgres:15.5-alpine              "docker-entrypoint.s…"   19 minutes ago   Up 19 minutes   5432/tcp                                plane-app-plane-db-1

➜  plane-app docker exec -it ef70f5708846 /bin/sh
/code # python3 manage.py test_email [user email]
Trying to send test email...
Error: Email could not be delivered due to (535, b'5.7.139 Authentication unsuccessful, SmtpClientAuthentication is disabled for the Tenant. Visit https://aka.ms/smtp_auth_disabled for more information. [YT1PR01CA0140.CANPRD01.PROD.OUTLOOK.COM 2024-05-15T16:11:37.399Z 08DC4B03C00638EE]')

[mologie]

Same issue on our test instance, but it is not related to SMTP authentication config at all.

The test command succeeds at sending, and the email is received:

/code # ./manage.py test_email [email protected]
Trying to send test email...
Email successfully sent

Users also get invite emails. However, after accepting the invite, the email login code on the login page is never delivered. (It is unclear to me why users can't set a password right away after invite either, seems counter-intuitive to have two mails after another.)

[pushya22]

@ReggieMarr @mologie Are you still facing the issue?

[ReggieMarr]

Yeah I found it was something to do with outlook, ending up working around with a a gmail account.

[mologie]

I don't know, we stopped demoing Plane after it had too many oddities with email setup. Just to list a few issues we found that contribute to this one:

• Changing email configuration in the admin panel would not apply until Plane was restarted. Refreshing would show the old information. This made stuff hard to debug.
• It was not possible to use an internal SMTP server without authentication. It refused to save at all.
• TLS toggles were inverted and every confusing (they changed text depending on state).
• Emails were not sent to a colleague of mine like described in a comment above. We later switched to AWS SES, same issue.

[isrealbm]

Same here. I was tested with SES, Mailtrap, and Sendgrid... all failed.

[mguptahub]

@pablohashescobar