Smtp relay on osx 10.9.5 and server 3.2.2

Question

What we have
We have a mac mini setup using 10.9.5 and server 3.2.2.    The mail server is OFF but we have a Relay Outgoing Mail through ISP checked (and the proper credentials for the outgoing relay (FQDN) and the authorization credentials.
What we are trying to do
Our mac mini runs a php script to generate an email that needs to be sent to users.   The mail has to use a smtp relay and we are trying to use the smtp relay provided by our email vendor.
Settings required by our email vendor
Instructions for configuring an email client can be found here
https://www.namecheap.com/support/knowledgebase/article.aspx/1179/2175/general-c onfiguration-for-mail-clients-and-mobile-devices
We set up the relay in Mail on the Server 3.2.2 to use SSL and port 465.  In our particular case the relay is configured as shown below.  Obviously the [email protected] is the proper username for our authorization.
When we try to send mail (we test this function by sending mail from terminal by using the following command (sending mail to myself from myself)
printf "Subject: TestnHello" | sendmail -f [email protected] [email protected]
and then watch the mail logs the smtp server rejects our mail due to authorization issues.  The mail log text is shown below (email addresses replaced with [email protected] and IP addresses modified)
Dec 22 11:57:03 109-218-164-81.lightspeed.austtx.sbcglobal.net postfix/pickup[16825]: 5545383231: uid=501 from=<[email protected]>
Dec 22 11:57:03 109-218-164-81.lightspeed.austtx.sbcglobal.net postfix/cleanup[16827]: 5545383231: message-id=<[email protected]bal.net>
Dec 22 11:57:03 109-218-164-81.lightspeed.austtx.sbcglobal.net postfix/qmgr[16826]: 5545383231: from=<[email protected]>, size=340, nrcpt=1 (queue active)
Dec 22 11:57:03 109-218-164-81.lightspeed.austtx.sbcglobal.net postfix/error[16838]: 5545383231: to=<[email protected]>, relay=none, delay=0.04, delays=0.02/0/0/0.02, dsn=4.4.1, status=deferred (delivery temporarily suspended: connect to eforwardct3.name-services.com[216.163.176.39]:465: Connection refused)
Dec 22 11:57:05 109-218-164-81.lightspeed.austtx.sbcglobal.net postfix/master[16824]: master exit time has arrived
We find many self help pages on the internet that talk about modifying the main.cf file located at /Library/Server/Mail/Config/postfix.   Some even talk about modifying settings in the master.cf file in /ect/postfix.  I have tried several and none seem to work.
Can anyone provide some guidance?
Regards!

Answer 1

The Server GUI doesn't provide for this use case.
Take the following steps to configure Postfix to relay mail to a remote SMTP server with password authentication over SSL. Substitute as required for strings in italics below. Address is the fully-qualified domain name of the relay host. The value of port is usually either 25, 465, or 587. Username and password refer to your credentials on the relay host.
In the current version of OS X Server (but not necessarily in older versions), Steps 1 and 3 should be done for you when you enable relaying and relay authentication in the Server application.
1. If necessary, create or update the relayhost directive in
     /Library/Server/Mail/Config/postfix/main.cf
It should look like this:
     relayhost = [address]:port
2. Add these lines, above the section at the end that begins with the comment "# Mac OS X Server":
     smtp_sasl_security_options =
     smtp_tls_CAfile = /etc/certificates/relayhost.pem
     smtp_tls_session_cache_database = btree:$data_directory/smtp_tls_session_cache
     smtp_use_tls = yes
3. If it doesn't already exist, create the password file
     /Library/Server/Mail/Config/postfix/sasl/passwd
with this content:
     [address]:port
     username:password
Here address must match $relayhost.
Then create the password database:
sudo postmap /Library/Server/Mail/Config/postfix/sasl/passwd
This action creates the file
     /Library/Server/Mail/Config/postfix/sasl/passwd.db
The two password files should be readable by root only.
4. Create the file
     /etc/certificates/relayhost.pem
with the CA certificate(s) to be trusted for authentication of the remote host. You get those certificates from the service provider. If you can't find a link to download them, try this:
openssl s_client -connect address:port -showcerts < /dev/null | sed -n '/-BEGIN /,/-END /p' | sudo sh -c 'cat > /etc/certificates/relayhost.pem'
The command may produce an error message that isn't necessarily significant. For servers that use the older STARTTLS protocol, rather than straight TLS or SSL, this command may need to be modified.
5. Restart the Mail service.