Can't configure SMTP sending (GMail)

[maaper]

Dear all, I have an instance of DOCUSEAL running on my Synology NAS in one docker container. It seems to work properly, but I'm not able to send any email. I have the two-factor authentication method on my Gmail account. I properly configure and obtain an app password.

Then I configured Docuseal as follow:

• Host: smtp.gmail.com
• Port: 465
• Username: my Google account
• Password: my generated APP Password (copy-pasting it)
• Send from mail: same than username

The issue is that im not able to send any mail, but I also not receiving any error message, so it's not possible for me to investigate deeply what can be wrong.

Thanks in advance. I used those guides for the installation: https://mariushosting.com/how-to-install-docuseal-on-your-synology-nas/ https://mariushosting.com/synology-set-up-email-notifications-on-docuseal/

[mariushosting]

I can't replicate this issue on different DocuSeal Instances. Everything is working like a charm on my end.

[maaper]

I tried to create a new user (email it supposed to be send to the user) so I can get some log with the hope of someone can help me to identify the issue.

2023-08-08T14:27:09.969742308Z I, [2023-08-08T14:27:09.969446 #1]  INFO -- : [90288fc8-fa5e-43f1-a4df-c748447827bc] [ActiveJob] Enqueued ActionMailer::MailDeliveryJob (Job ID: 78c423fd-d7b8-4a9d-8270-4dd1a9428f1f) to Async(default) with arguments: "UserMailer", "invitation_email", "deliver_now!", {:args=>[#<GlobalID:0x00007fefccde9630 @uri=#<URI::GID gid://docu-seal/User/3>>]}
2023-08-08T14:27:09.971400683Z I, [2023-08-08T14:27:09.971217 #1]  INFO -- : [90288fc8-fa5e-43f1-a4df-c748447827bc] {"method":"POST","path":"/users","format":"turbo_stream","controller":"UsersController","action":"create","status":302,"duration":105.01,"view":0.0,"db":21.72,"location":"https://docuseal.cnlb.es/settings/users","fwd":"172.19.0.1"}
2023-08-08T14:27:09.974817777Z I, [2023-08-08T14:27:09.974603 #1]  INFO -- : [ActiveJob] [ActionMailer::MailDeliveryJob] [78c423fd-d7b8-4a9d-8270-4dd1a9428f1f] Performing ActionMailer::MailDeliveryJob (Job ID: 78c423fd-d7b8-4a9d-8270-4dd1a9428f1f) from Async(default) enqueued at 2023-08-08T14:27:09Z with arguments: "UserMailer", "invitation_email", "deliver_now!", {:args=>[#<GlobalID:0x00007fefcce3a828 @uri=#<URI::GID gid://docu-seal/User/3>>]}
2023-08-08T14:27:10.050507599Z I, [2023-08-08T14:27:10.050292 #1]  INFO -- : [e8275cb4-0362-48af-a7cd-8a0660120be2] {"method":"GET","path":"/settings/users","format":"turbo_stream","controller":"UsersController","action":"index","status":200,"duration":14.7,"view":8.06,"db":1.64,"fwd":"172.19.0.1"}
2023-08-08T14:27:15.030262938Z E, [2023-08-08T14:27:15.029902 #1] ERROR -- : [ActiveJob] [ActionMailer::MailDeliveryJob] [78c423fd-d7b8-4a9d-8270-4dd1a9428f1f] Error performing ActionMailer::MailDeliveryJob (Job ID: 78c423fd-d7b8-4a9d-8270-4dd1a9428f1f) from Async(default) in 5059.9ms: Errno::EADDRNOTAVAIL (Address not available - connect(2) for [2a00:1450:4025:402::6c]:465):

[maaper]

Looking at the log in detail, the error seems to be here, but I dont know how to solve.

E, [2023-08-08T14:44:36.053629 #1] ERROR -- : [ActiveJob] [ActionMailer::MailDeliveryJob] [3a31fe6f-1111-4321-8f4b-521b2ce18bb3] Error performing ActionMailer::MailDeliveryJob (Job ID: 3a31fe6f-1111-4321-8f4b-521b2ce18bb3) from Async(default) in 5072.58ms: Errno::EADDRNOTAVAIL (Address not available - connect(2) for [2a00:1450:4025:402::6d]:465):

[maaper]

I found the solution. I don't know why but if I use port 587 instead of 465 on the configuration it works.

@mariushosting perhaps it can help to anyone else 👍

Thanks!!