Rundeck GMail SMTP not working

Question

I'm setting up Rundeck but can't get notification emails working. Here's the config:

grails.mail.host = "smtp.gmail.com"
grails.mail.port = 465
grails.mail.username = "peter@blahblah.com"
grails.mail.password = "blahblahblah"
grails.mail.props = ["mail.smtp.starttls.enable":"true","mail.smtp.auth":"true","mail.smtp.socketFactory.port":"465","mail.smtp.socketFactory.class":"javax.net.ssl.SSLSocketFactory","mail.smtp.socketFactory.fallback":"false"]

and here's the error:

2015-06-02 12:17:49,142 ERROR NotificationService - Error sending notification email to peter@blahblah.com for Execution 29: Mail server connection failed; nested exception is com.sun.mail.util.MailConnectException: Couldn't connect to host, port: "smtp.gmail.com", 465; timeout -1;

I've poked holes at both 465 and 587 in the (Windows) firewall (in fact, I turned it off completely temporarily and got the same exception).

Try to connect to the mail server using telnet ?Like `telnet smtp.gmail.com 465`. Try this command and see if you are able to connect.. — Racer, Jun 04 '15 at 11:56
@Racer yep it connects (i.e. I do not get a "Could not open..." message) — sming, Jun 06 '15 at 20:01
I am having problems configuring gmail smtp on Rundeck. Where should I put the smtp settings? — Lucas Rezende, May 05 '16 at 17:20
Check my answer: http://stackoverflow.com/questions/37057245/rundeck-gmail-smtp-not-working- smtp-gmail-com-unknown-host/38761317#38761317 — yogs, Aug 04 '16 at 07:45

score 3 · Accepted Answer · answered Sep 16 '20 at 14:30

Just for the record answer: Currently you need to create a rundeck-config.groovy file (at /etc/rundeck path) with Gmail server configuration (only the email configuration) like this:

grails {
  mail {
    host = "smtp.gmail.com"
    username = "username@gmail.com"
    port = 587
    password = "example"
    props = ["mail.smtp.starttls.enable":"true","mail.smtp.auth":"true","mail.smtp.socketFactory.port":"587","mail.smtp.socketFactory.fallback":"false"]
  }
}
grails.mail.default.from = "username@gmail.com"

The main reason of this is that .config file by design doesn't support extended features by external provider like gmail or office365. Check this.

Rundeck GMail SMTP not working

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