I am running Webmin on Ubuntu 10.10 and have Sendmail setup as my MTA. I can do a cli of sendmail to my personal '@mac.com' and to my personal '@gmail.com' accounts without problem, but I cannot send to our corporate gmail app and get the standard 'reason: 530 5.7.0 Must issue a STARTTLS command first.'
I've been following different threads, creating certs attempting to setup a relay, but am pretty new to this legacy system I've inherited. Feel like it should just be easy through the Sendmail setup in Webmin. Any help would be appreciated. I've noticed our gmail business app has ssl turned off on the mail settings; should this be on to make it work?