A customer needs to send emails from a Programmable Logic Controller (PLC) which cannot provide authentication. The customer's email server is gmail which obviously requires authentication. The PLC IP is 192.168.1.2 and the PC IP on which stunnel is installed is 192.168.1.31 My config is: cert = stunnel.pem [smtps] client = yes accept = 25 connect = smtp.gmail.com:465 The PLC is set up to send emails to the IP of the PC 192.168.1.31 When I try to send emails I get the following in the stunnel log: 2013.06.26 14:26:30 LOG5[12384:13048]: Service [smtps] accepted connection from 192.168.1.2:2938 2013.06.26 14:26:30 LOG5[12384:13048]: connect_blocking: connected 74.125.130.108:465 2013.06.26 14:26:30 LOG5[12384:13048]: Service [smtps] connected remote server from 192.168.1.31:53599 Any help would be greatly appreciated! Stephen Gates Harold K. Scholz Company 7800 Serum Avenue Ralston, NE 68127 402-339-7600