Hi again! >>> > Is it possible to use port 465? Yes. With "-starttls smtp" chunk removed from -H option. That is what I used: # sendmail -H "exec openssl s_client -quiet -connect smtp.gmail.com:465 -tls1" -f dronnikov at gmail.com -F "Vladimir Dronnikov" 4<.cred > > Best regards, > -- > Vladimir >