SMTP Outbound Connection Test Validation Failed with Error "Could not convert socket to TLS"

Products

• VMware Aria Suite

Issue/Introduction

On Outbound Settings, "Test Validation" failed to endpoint SMTP server with the following error:

Could not convert socket to TLS

Environment

VMware Aria Operations 8.14

Cause

The remote smtp server certificate cannot be trusted.  The following error is showing on the analytic log:

'Test email from VMware Aria Operations email plugin'; com.vmware.vcops.platform.notification.email.EmailSender.call - details: javax.mail.MessagingException: Could not convert socket to TLSjavax.net.ssl.SSLHandshakeException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certificate path to request target

Resolution

• Perform an openssl to the endpoint to validate the certificate chain:
  • openssl s_client -connect <SMTP_FQDN_or_IP>:25 -showcerts
• Review the certificate.  Capture the Root certificate.
• Save the root certificate as a .pem file.
• Login to Aria Operations.  
  • Go to Administration/Certificates
  • Click <Import> and import the pem file.
• Go back to Outbound Settings, and perform another "Test Validation".  The validation should be successful.