I've gone as far as I can go on my own, but I'm not a Linux guru and am now stuck.
I've got an Oracle database running Oracle Enterprise Linux 5.1 on an Amazon EC2 instance. I migrated it from a box that was connected via a home broadband connection, and it was sending emails without problem via the ISP's SMTP server - but now that it is running on EC2, the ISP doesn't recognise it and refuses to accept the emails.
So now I want to set it up, the simplest way possible, so that it can continue to send emails.
I've tried emailrelay as per instructions here: http://jiri.wordpress.com/2010/03/24/send-emails-using-utl_mail-and-google-gmail-smtp-server/#comment-108
I had problems getting it to work because openssl wasn't installed:
$ emailrelay –as-proxy smtp.gmail.com:587 –client-tls –client-auth /etc/emailrelay.auth –port 8025 emailrelay: error: cannot do tls/ssl: openssl not built in emailrelay: exception: cannot do tls/ssl: openssl not built in
But it wouldn't work because it requires openssl-devel, which I can't install on my system (I couldn't find the dependencies:
$ rpm -i openssl-devel-0.9.7a-2.i386.rpm warning: openssl-devel-0.9.7a-2.i386.rpm: Header V3 DSA signature: NOKEY, key ID db42a60e error: Failed dependencies: krb5-devel is needed by openssl-devel-0.9.7a-2.i386 openssl = 0.9.7a-2 is needed by openssl-devel-0.9.7a-2.i386
I gave up at that point because I couldn't find krb5-devel available for Oracle Enterprise Linux 5.1.
I had a look at this sendmail option: http://www.phinesolutions.com/sendmail-gmail-smtp-relay-howto.html
But this doesn't work because sendmail wasn't compiled with "TLS" or "SASL" options, and how to fix this wasn't covered.
Am I making this more difficult than it has to be? Is there a simple way to send emails from Linux? I have a Google Apps account associated with the domain name.