Sendmail Configuration SMTP Relay Port 465

I am trying to setup a Ubuntu VM with sendmail (LAMP) and I cannot seem to get sendmail to actually send anything. I have read that I need to setup a SMTP relay to a valid domain name, which I have (not Gmail).

Here are the steps that I am taking (as root):

apt-get install sendmail mailutils
cd /etc/mail
mkdir auth
chmod 700 auth
vi auth/client-info
    AuthInfo:mail.<mydomain.net> "U:user" "I:user" "P:password"
    TLS_Srv:mail.<mydomain.net> ENCR:128
makemap hash auth/client-info < auth/client-info
chmod 600 auth/client-info
vi sendmail.mc
    After MAILER_DEFINITIONS:
    Add define(`SMART_HOST',`mail.<mydomain.net>')dnl
    define('confAUTH_MECHANISMS', 'EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl
    FEATURE('authinfo','hash /etc/mail/auth/client-info')dnl
m4 sendmail.mc > sendmail.cf

When I test it, I do

(echo subject: test; echo ) | sendmail -v -i -Am -- [email protected]

and it seems like it hangs on this without doing anything.

In my error log, /var/log/mail.err I have the following:

Mar 24 09:40:01 webDev sm-msp-queue[15397]: My unqualified host name (webDev) unknown; sleeping for retry
Mar 24 09:41:01 webDev sm-msp-queue[15397]: unable to qualify my own domain name (webDev) -- using short name

The only thing that I cannot figure out is how to use a different port since the server is setup to use port 465. Connection security is SSL/TLS and plaintext password.

What am I missing to get this configuration working?

EDIT: I have changed /etc/hosts and set my computername to a FQDN and it no longer seems like it is hanging.

I now have a problem "Deferred: Connection refused by " Using Wireshark I have found the packets being sent to mail. are on port 25. An Nmap scan of mail. port 25 as closed.

At this point I have abandoned the idea of using my host as a sendmail relay and moved over to using Gmail.

I found a bunch of sites that helped get it configured. I have tested this on Ubuntu and CentOS... I hope it can be of some help to someone.

apt-get update

vi /etc/hostname
# Enter valid FQDN name

apt-get install sendmail sendmail-cf sasl2-bin

cd /etc/mail
mkdir certs
chmod 700 certs/
cd certs/

openssl dsaparam 1024 -out dsa1024.pem
openssl req -x509 -nodes -days 3650 -newkey dsa:dsa1024.pem -out /etc/mail/certs/mycert.pem -

keyout /etc/mail/certs/mykey.pem
# Enter "US" for Country Name (Can leave everything else blank)

openssl req -x509 -new -days 3650 -key /etc/mail/certs/mykey.pem -out 

/etc/mail/certs/mycert.pem
# Enter "US" for Country Name (Can leave everything else blank)

ln -s /etc/mail/certs/mycert.pem /etc/mail/certs/CAcert.pem
chmod 600 /etc/mail/certs/*

cd ..
mkdir auth
chmod 700 auth/

vi auth/client-info

content:

AuthInfo:smtp.gmail.com "U:root" "I:<emailAddress>@gmail.com" "P:password"
AuthInfo: "U:root" "I:<emailAddress>@gmail.com" "P:password"

then,

makemap -r hash /etc/mail/auth/client-info.db < /etc/mail/auth/client-info

vi sendmail.mc

Above "MAILER(local)dnl" Add:

dnl #
dnl # SSL Settings
define(`CERT_DIR', `MAIL_SETTINGS_DIR`'certs')
define(`confCACERT_PATH', `CERT_DIR')
define(`confCACERT', `CERT_DIR/CAcert.pem')
define(`confSERVER_CERT', `CERT_DIR/mycert.pem')
define(`confSERVER_KEY', `CERT_DIR/mykey.pem')
define(`confCLIENT_CERT', `CERT_DIR/mycert.pem')
define(`confCLIENT_KEY', `CERT_DIR/mykey.pem')
dnl #
dnl # GMAIL FORWARDING
define(`SMART_HOST',`smtp.gmail.com')dnl
define(`RELAY_MAILER_ARGS', `TCP $h 587')dnl
define(`ESMTP_MAILER_ARGS', `TCP $h 587')dnl
define(`confAUTH_OPTIONS', `A p')dnl
TRUST_AUTH_MECH(`EXTERNAL DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl
define(`confAUTH_MECHANISMS', `EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl
FEATURE(`authinfo',`hash -o /etc/mail/auth/client-info.db')dnl

afterwards,

m4 sendmail.mc > sendmail.cf

service sendmail stop

service sendmail start

(echo subject: test; echo ) | /usr/sbin/sendmail -v -i -Am -- [email protected]