Error: "Unable to send email for Organization '####' and following destination address '####@####'" sending test email

Products

• VMware Cloud Director

Issue/Introduction

• When trying to configure an SMTP server to send email notifications in VMware Cloud Director Availability (VCDA) while sending a test email you get an error:
  
  Error: "Unable to send email for Organization '####' and following destination address '####@####'" sending test email.
  
  
• In /opt/vmware/h4/cloud/cloud.log on the loud Director Replication Management Appliance you can see entries similar to:
  
  DEBUG - [UI-########-####-####-####-############-#####-##] [job-##] c.v.h.c.event.email.BaseEmailService     : Error when sending emails
org.springframework.mail.MailSendException: Mail server connection failed; nested exception is javax.mail.MessagingException: Could not convert socket to TLS;
nested exception is:
javax.net.ssl.SSLHandshakeException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target. Failed messages: javax.mail.MessagingException: Could not convert socket to TLS;
  
  
• The SMTP server you are using has self signed or internally signed certificates.

Environment

VMware Cloud Director Availability 4.x.

Cause

VCDA requires a publicly validated certificate to establish a secure connection with an SMTP server. The service lacks a mechanism to manually trust or import self-signed certificates for mail delivery.

Resolution

This is expected behavior within the VMware Cloud Director Availability 4.x product architecture.

Additional Information

You can configure email servers with certificates issued by a publicly recognized Certificate Authority or use VMware Cloud Director to send the notification emails following this documentation Configure tenant event notifications in the Cloud Director site