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Has anyone been able to route outgoing mail through Google using another non-Gmail SMTP service?

I currently have a website running with Bitnami vm running a CanvasLMS application on a Google Cloud Platform server.

When entering my GSuite Gmail Advanced Settings, the required steps have been done to configure the SMTP relay service. (TLS set to true)

https://support.google.com/a/answer/2956491?hl=en&authuser=3&ref_topic=2921034

I have also configured the setup for the outgoing email server at /apps/canvaslms/htdocs/config/outgoing_mail.yml (replacing username and password with my application's credentials)

production:
  enable_starttls_auto: true
  address: smtp-relay.gmail.com
  port: 587
  user_name: USERNAME@gmail.com
  password: PASSWORD
  authentication: plain        # plain, login, or cram_md5
  domain: smtp-relay.gmail.com
  outgoing_address: USERNAME@gmail.com
  default_name: CANVAS LMS

Saved the changes and restarted the server. When trying to send an email in Canvas for new user registration, it never reaches the receivers email inbox.

I have reviewed my application logs and have not discovered any errors related to this

Any thoughts on troubleshooting this SMTP issue???

https://docs.bitnami.com/installer/apps/canvaslms/configuration/configure-smtp/ https://community.canvaslms.com/t5/Question-Forum/emails-are-not-sent-to-users-students/m-p/230561#M128347

Digil
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Whitney Moore
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  • Most likely, G Suite is rejecting your authentication. Depending on how you have PHP configured for error logging, you will find details in one of the log files (syslog, php_error.log, etc). On most systems, there are two `php.ini` files. One for Apache and the other for the PHP CLI. You need to review the Apache `php.ini`. The function `phpinfo()` will report the location of `php.ini`. – John Hanley Sep 18 '20 at 00:09
  • Hi John, Thanks for the tip! After editing the php.ini file to allow for logs and defining the php error log path. I created a php error log file and gave the appropriate read and write permissions, restarted the server, sent some emails and not seeing any errors in the php error log. Any thoughts? – Whitney Moore Oct 02 '20 at 00:24
  • Did you turn on debugging? – John Hanley Oct 02 '20 at 01:04
  • @JohnHanley is that configuration done in php.ini or elsewhere? – Whitney Moore Oct 05 '20 at 19:58
  • PHP logging is configured in `php.ini`. Your library might also have options. https://rollbar.com/guides/where-are-php-errors-logged/ – John Hanley Oct 06 '20 at 02:52

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