@scottalanmiller Ok, I think I got it. Per http://bugs.elastix.org/view.php?id=2549:

Starting with PHPMailer v5.2.7, the default HELO hostname is not set anymore to 'localhost' if not supplied on the Hello() function... This generates that the Elastix remotesmtp configuration checker ends up sending an empty HELO/EHLO command, which makes Gmail (and probably many other SMTP servers) really unhappy.

A possible solution would be to modify /var/www/html/modules/remote_smtp/libs/paloSantoEmailRelay.class.php on line 156:

if(!$smtp->Hello()){

change to:

if(!$smtp->Hello(getHostname())){

If you are using the Multi Tenant version the location is /usr/share/elastix/apps/remote_smtp/libs/paloSantoEmailRelay.class.php

Changed that and it worked. However, whenever I create a new organization and the email is sent to the "admin", I never receive anything... what could it be now? Any ideas? Thanks!

@scottalanmiller Ok, I think I got it. Per http://bugs.elastix.org/view.php?id=2549:

Starting with PHPMailer v5.2.7, the default HELO hostname is not set anymore to 'localhost' if not supplied on the Hello() function... This generates that the Elastix remotesmtp configuration checker ends up sending an empty HELO/EHLO command, which makes Gmail (and probably many other SMTP servers) really unhappy.

A possible solution would be to modify /var/www/html/modules/remote_smtp/libs/paloSantoEmailRelay.class.php on line 156:

if(!$smtp->Hello()){

change to:

if(!$smtp->Hello(getHostname())){

If you are using the Multi Tenant version the location is /usr/share/elastix/apps/remote_smtp/libs/paloSantoEmailRelay.class.php

Changed that and it worked. However, whenever I create a new organization and the email is sent to the "admin", I never receive anything... what could it be now? Any ideas? Thanks!

@scottalanmiller True. Same outcome as expected whether firewall is off or not. There is no external firewall given this is a cloud-hosted (digital ocean) server, is there?

@scottalanmiller Maybe firewall rules?

@scottalanmiller Thanks for the quick reply! Tried it and it sent me an email (although went straight to my junk folder). Email came from [email protected].

@scottalanmiller Thanks for the script! I was able to install Elastix MT on a cloud server from Digital Ocean running CentOS 6.8 64-bit. I am having an issue and I was wondering if you could help me. I am trying to configure the server, and the first step I usually do is set up the Email > Remote SMTP. I usually use a gmail account, but I am getting an error saying that it "Failed to send hello command" and it won't let me keep the status to ON. I am at a loss... Do you have some light you can shed to this? Thank you in advance for your time and response.

P.S > I think the script ran successfully, but I got a lot of "Missing; Nothing to do" messages when running the "for i in $(ls); do yum -y install $i; done" commands. In fact, the second time I ran it, it was all about those messages. Nothing really installed. The first time around, it downloaded and ran many items.