Unable to setup SMTP using TLS on port 587

We have been trying to setup the smtp server configuration under Jira. We have been trying to use SMTP over TLS on port 587. So far only SMTP unsecured over port 25 seems to be working. We need to a secure SMTP connection. 

1 answer

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Hi Juan,

When you state this is not working are you getting an error message or do you just not see messages coming through? 

If you cannot paste the full error message here, perhaps you can copy and paste it into a text editor and upload it as an attachment here.

In the meantime, have you reviewed the information in Configuring JIRA's SMTP mail server to send notifications?:

SMTP over SSL

You can encrypt email communications between JIRA and your mail server via SSL, provided your mail server supports SSL. 

Firstly, you will need to import the SMTP server certificate into a Java keystore. The process is described on the Configuring an SSL connection to Active Directory page.

(warning) Important Note: Without importing the certificate, JIRA will not be able to communicate with your mail server.

Secondly, edit your mail server connection properties and specify starttls and SSLSocketFactory. From {$JIRA_INSTALL}/conf/server.xml (this example uses Gmail's server):

<Resource name="mail/GmailSmtpServer"
 auth="Container"
 type="javax.mail.Session"
 mail.smtp.host="smtp.gmail.com"
 mail.smtp.port="465"
 mail.smtp.auth="true"
 mail.smtp.user="myusername@gmail.com"
 password="mypassword"
 mail.smtp.starttls.enable="true"
 mail.smtp.socketFactory.class="javax.net.ssl.SSLSocketFactory"
/>

Review the above info and if you believe it's setup correctly according to those directions, the next step would be to provide the error message(s) you received.

Cheers,

Branden

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