Great thought to check the generated file. It looks OK. grep gmail sendmail.* sendmail.cf:DSsmtp-relay.gmail.com sendmail.cf.bak:DSsmtp-relay.gmail.com sendmail.mc:define(`SMART_HOST', `smtp-relay.gmail.com') dnl host smtp-relay.gmail.com smtp-relay.gmail.com has address 64.233.176.28 smtp-relay.gmail.com has IPv6 address 2607:f8b0:4002:c02::1c service sendmail restart again - and same behavior going to relay 203.inbound-mx.org Jerry