In an earlier issue I found that the JRE that comes with Jira 6.3.3. is corrupt. In my instance it couldn't find the correct SSL certs.
Now that that is fixed, I have a new follow-up problem: SMTP authentication always fails.
I have 2 G-apps accounts, I tried both. On one I am a regular user, and figured I needed to be an admin of sorts to fix this. So I tried another google apps acount. The latter has 2-factor auth, but I used an app-password to get around that. Both result is:
Unfortunately no connection was possible. Review the errors below and rectify:
AuthenticationFailedException: 535 Incorrect authentication data
However, I tripple checked the data and logged in with that same data in my gmail env.
The SMTP log shows that the details aren't correct either, which makes me wonder what's going on...
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtps,com.sun.mail.smtp.SMTPSSLTransport,Sun Microsystems, Inc]
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 465, isSSL true
220-vps.xxx.com ESMTP Exim 4.82 #2 Mon, 18 Aug 2014 15:10:43 +0200
220-We do not authorize the use of this system to transport unsolicited,
220 and/or bulk e-mail.
DEBUG SMTP: connected to host "smtp.gmail.com", port: 465
EHLO vps.xx.com
250-vps.xx.com Hello vps.xx.com [###.###.###.###]
250-SIZE 52428800
250-8BITMIME
250-PIPELINING
250-AUTH PLAIN LOGIN
250 HELP
DEBUG SMTP: Found extension "SIZE", arg "52428800"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Found extension "AUTH", arg "PLAIN LOGIN"
DEBUG SMTP: Found extension "HELP", arg ""
DEBUG SMTP: Attempt to authenticate
DEBUG SMTP: check mechanisms: LOGIN PLAIN DIGEST-MD5 NTLM
DEBUG SMTP: AUTH LOGIN command trace suppressed
DEBUG SMTP: AUTH LOGIN failed
should I delete the mail settings (is there a specific file for this?) and start over to remove any cache?
---------- EDIT ---------------------
I installed v6.2.7 on the vps to see if there's something wrong with either my install or the 6.3.3. package in general. But no help here. 6.2.7 is now giving me the SSL issues I had earlier (see: https://answers.atlassian.com/questions/325709/error-setting-up-gmail-in-jira-633-suncertpathbuilderexception/325806)
------- EDIT 21/8 ---------------
I noticed that we have a local exim running (apparently comes with cpanel). That does work. Perhaps the local exim interferes with the connection/authenticatrion protocol?
The problem is solved, albeit in a work-around manner.
