Symptoms

When trying to execute an email event the following error was being recorded:

"939486","2016-07-12 09:33:53","Error","General","0","ErrorMessage","SourceCode.Workflow.Common.SmtpMail","0 SMTP mail send failure: Verify the SMTP connection strings are correct and that SMTP is working properly. Exception: Server does not support secure connections.","anonymous","0.0.0.0","USOLGWKXNV029:C:Program Files (x86)K2 blackpearlHost ServerBin","939486","8d870d36fec04726a251659cc173702a",""
 

Diagnoses

In this scenario the issue was caused by a difference in the SSL configuration between the K2 server and the SMTP server in where the K2 server was configured for SSL but the SMTP server was not.

 

Resolution

In the connectionstring editor we set the connection string TLS property to none from "BootTLS"