Raley is relying on JIRA's outgoing mail server to send email notifications. In some cases (JRASERVER-39740 - SSLException when configuring outgoing mail to use the Office 365 SMTP Server VERIFIED ) you might want to define an outgoing email server via JNDI and the sending of outgoing test email will work  nicely, however, when you need to send an email from Raley, something like the following will appear in log:

 

2018-01-25 22:52:47,658 Sending mailitem To='vovan@me.com' Subject='Local Listing Maintenance Request Received (CPROVLSEOQ-37)' From='null' FromName='null' Cc='null' Bcc='null' ReplyTo='null' InReplyTo='null' MimeType='text/plain' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@3c827ec1' MessageId='null' ExcludeSubjectPrefix=false' ERROR Providence Local Service Desk 1372x5514x1 p24o6h 96.66.254.49,127.0.0.1 /secure/admin/MailQueueAdmin.jspa [c.a.mail.queue.MailQueueImpl] Error occurred in sending e-mail: To='vovan@me.com' Subject='Local Listing Maintenance Request Received (CPROVLSEOQ-37)' From='null' FromName='null' Cc='null' Bcc='null' ReplyTo='null' InReplyTo='null' MimeType='text/plain' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@3c827ec1' MessageId='null' ExcludeSubjectPrefix=false'
com.atlassian.mail.MailException: com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM...

 

In this scenario you must explicitly specify fromName and fromAddress in Raley Notifications. Open a Settings tab and add the following to your properties:

outgoing_email.from_address=you@yourcompany.com
outgoing_email.from_name=Your Name

 

You can also customise the fromName and fromAddress as per JIRA project. Remember, every Raley notifications is connected to specific project and that's said you can use different fromName and fromAddress as per project. Again, you have to configure it in your properties using project key as a suffix:

 
outgoing_email.from_address=you@yourcompany.com
outgoing_email.from_name=Your name
outgoing_email.from_address.ABC=me@yourcompany.com
outgoing_email.from_name.ABC=My own name
outgoing_email.from_address.xyz=somebody@yourcompany.com
outgoing_email.from_name.xyz=Somebody's name
In the example above, all the notifications from project ABC will be sent from me@yourcompany.com and from project xyz from somebody@yourcompany.com. Note, that project key is not case-sensitive. 
All other notifications will be sent using you@yourcompany.com