I have setup my machine to relay through smtp.gmail.com installed cyrus-sasl-md5 cyrus-sasl-plain Added to access: AuthInfo:smtp.gmail.com "U:smmsp" "I:my accont" "P:my pass" "M:PLAIN" AuthInfo:smtp.gmail.com:587 "U:smmsp" "I:my account" "P:my pass" "M:PLAIN" Added to sendmail.mc the SMART_HOST smtp.gmail.com uncommented the pki lines define(`confCACERT_PATH', `/etc/pki/tls/certs')dnl define(`confCACERT', `/etc/pki/tls/certs/ca-bundle.crt')dnl define(`confSERVER_CERT', `/etc/pki/tls/certs/sendmail.pem')dnl define(`confSERVER_KEY', `/etc/pki/tls/certs/sendmail.pem')dnl set the confAUTH_MECHANISMS restarted sendmail It seems like sendmail is trying to use port 25 as the log shows "connection timeout". I did this to two other machines and it worked. the third one is being stubborn. Any suggestions to look at ??? Jerry