Technology Insights

Redmine: The following error occured while sending email notification: 530 5.7.0 Must issue a STARTTLS command first.

Recently while working on a CentOS Linux server I downgraded Ruby version 1.8.7 p302 to Ruby version 1.8.6 p399 because of a project that was built for Ruby 1.8.6. The server is a development CentOS Linux server with numerous other projects already operational on it and so downgrading Ruby caused a couple issues one of which was with Redmine project management software. The issue was with sending email notifications for things such as file uploads, added issues, issue updates, etc. Below I describe the error in more detail, the reason for the error, and how to resolve the error sending email notifications.

Technology Errors

STARTTLS: read error=generic SSL error

When receiving this error you are either having a STARTTLS problem or there is a chance that it is a bug in sendmail and you just need to supply a patch to sendmail. First to resolve the issue follow the below steps.

1. Stop sendmail: /etc/init.d/sendmail stop
2. Make sure the PID’s all stopped: ps -ef | grep sendmail
3. If not kill the stuck process ID’s: kill -9
4. Also check the PID’s from the maillog where you originally saw the error and make sure those are not running.
5. Start sendmail: /etc/init.d/sendmail start