Configuring Jira to use Gmail via SMTP

Here is the notes from work to setup SMTP for Jira on Windows:

1. Download openssl
   
2. Run: openssl s_client -connect smtp.gmail.com:465> gmail.pem
   
3. Edit gmail.pem with notepad
   
4. Remove everything exception of "-----BEGIN CERTIFICATE-----" to "-----END CERTIFICATE-----" (the BEGIN and END portion must be retained)
   
5. Save it
   
6. Run: keytool -import -file gmail.pem -alias smtp.gmail.com -keystore "C:\Program Files\Java\jre1.6.0_05\lib\security\cacerts"
   
7. keytool comes with Java in the bin dir
   
8. lib\security\cacerts is within the Java install dir
   
9. Edit C:\Program Files\JIRA-Enterprise-3.13.4\conf\server.xml
   
10. Obviously file is relative to your install
    
11. Add the below node to Context element but change relevant settings:
    
12. <resource name="mail/GmailSmtpServer" class="Apple-tab-span" style="white-space:pre"> auth="Container"
    type="javax.mail.Session"
    mail.smtp.host="smtp.gmail.com"
    mail.smtp.port="465"
    mail.smtp.auth="true"
    mail.smtp.user="MyGmailAccount@gmail.com"
    password="MyPassword"
    mail.smtp.starttls.enable="true
    mail.smtp.socketFactory.class="javax.net.ssl.SSLSocketFactory" 
    />
    
13. Save file
    
14. Move 
    
15. Files:
    
16. javamail-1.3.3.jar
    
17. activation-1.0.2.jar
    
18. From: c:\Program Files\JIRA-Enterprise-3.13.4\atlassian-jira\WEB-INF\lib\
    
19. To: c:\Program Files\JIRA-Enterprise-3.13.4\common\lib
    
20. Restart Atlassian JIRA service
    
21. Go to Adminstration in JIRA web
    
22. Go to Mail Servers
    
23. Configure the SMTP
    
24. Use JNDI setting: java:comp/env/mail/GmailSmtpServer
    
25. Pray to God it works!
    

References:

http://www.customware.net/repository/pages/viewpage.action?pageId=36470958

http://www.atlassian.com/software/jira/docs/latest/smtpconfig.html#SMTP+over+SSL

http://confluence.atlassian.com/display/JIRA/Connecting+to+SSL+services