When attempting to use the 'Send email alert' assertion with Office365 you may encounter the below error
530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM
When the Gateway completes a SSL handshake with the SMTP server the Gateway almost immediately generates an additional ClientHello (starts a renegotiation handshake) and SMTP server returns a TCP RST.
To prevent this add the com.l7tech.server.policy.emailalert.useDefaultSsl system property to bypasses the additional renegotiation.
1. Connect to the Gateway and edit: /opt/SecureSpan/Gateway/node/default/etc/conf/system.properties
2. Add this property com.l7tech.server.policy.emailalert.useDefaultSsl=TRUE
3. Save the file and restart the gateway.
4. It is assumed that office365 root certificate is added to the gateway( Policy manager-> Manage Certificates)
5. In Email alert properties select protocol as “SMTP with STARTTLS” port 25/587.
6. Select Server Required Authentication checkbox.
7. Domain name must be provided for all user names and emails ids(Ex: firstname.lastname@example.org).
8. Adding proper email ids it should send email normally.