Email send stopped working

Self-Hosted | v5
1

Hi.

As of recently email are not being sent out anymore. Didn’t touch a thing except did the Invoice Ninja updates.

Changing TSL, SSL, ports doesn’t seem to change anything. I can send out e-mail using telenet from ac ommand line.

So what is the very less stressful procedure to test email sending? How should I proceed to troubleshoot.

What I do now…

  • change and save.env file
  • php artisan optimize
  • clear cache
  • resend (email) the exisiting quote

-env settings that used to work before
MAIL_MAILER=smtp
MAIL_HOST=mail.mydomain.com
MAIL_PORT=25
MAIL_USERNAME=payments.mydomain.com
MAIL_PASSWORD=xxxxxxxxxxxxxxxxx
MAIL_ENCRYPTION=
MAIL_FROM_ADDRESS=payments@mydomain.com
MAIL_FROM_NAME=Payments

LOG
[2022-08-12 14:23:01] production.INFO: trying to send to mytestaddress@gmail.com 2022-08-12 14:23:01
[2022-08-12 14:23:01] production.INFO: Using mailer => smtp
[2022-08-12 14:23:01] production.INFO: error failed with Failed to authenticate on SMTP server with username “payment
s.dbstudio.si” using the following authenticators: “LOGIN”, “PLAIN”. Authenticator “LOGIN” returned “Expected respons
e code “235” but got code “535”, with message “535 5.7.8 Error: authentication failed: authentication failure”.”. Aut
henticator “PLAIN” returned “Expected response code “235” but got code “535”, with message “535 5.7.8 Error: authenti
cation failed: authentication failure”.”.

2

Hi,

@david any thoughts?

3

Wait, it works for new quotes, but won’t resend out old ones. Strange, but it works.

Please ignore it.

Thank you for quick response Hillel.

Br,
Dali

1 Like
4

ok but I have the same issue but want to be able to send old ones because my reminders are not send out.

production.INFO: error failed with Failed to authenticate on SMTP server with username “” using the following authenticators: “LOGIN”, “XOAUTH2”. Authenticator “LOGIN” returned “Expected response code “235” but got code “535”, with message “535 5.7.3 Authentication unsuccessful [AM0PR04CA0039.eurprd04.prod.outlook.com 2023-03-17T15:37:07.478Z 08DB2699D0179B67]”.”. Authenticator “XOAUTH2” returned “Expected response code “235” but got code “535”, with message “535 5.7.3 Authentication unsuccessful [AM0PR04CA0039.eurprd04.prod.outlook.com 2023-03-17T15:37:18.274Z 08DB2699D0179B67]”.”.