Lost SMTP Authentication along the way

At work we have our OS X mail server set to require smtp authentication. This works from within the network. However, once you go off the network, you can no longer send mail if you use smtp authentication. If you set up your smtp settings to not use authentication however, it works fine. This is a huge security hole for us. What could possibly be causing this?

I am able to send to my own email domain without authentication, but am unable to send from off my domain, to off my domain with or without authentication. Here is my postconf -n
alias_maps = hash:/etc/aliases,hash:/var/mailman/data/aliases
command_directory = /usr/sbin
config_directory = /etc/postfix
content_filter = smtp-amavis:[127.0.0.1]:10024
daemon_directory = /usr/libexec/postfix
debugpeerlevel = 2
enableserveroptions = yes
html_directory = no
inet_interfaces = all
localrecipientmaps = proxy:unix:passwd.byname $alias_maps
luser_relay =
mail_owner = postfix
mailboxsizelimit = 0
mailbox_transport = cyrus
mailq_path = /usr/bin/mailq
manpage_directory = /usr/share/man
mapsrbldomains =
messagesizelimit = 0
mydestination = $myhostname,localhost.$mydomain,list.solon.k12.ia.us,solon.k12.ia.us,localhost
mydomain = solon.k12.ia.us
mydomain_fallback = localhost
myhostname = solon.k12.ia.us
mynetworks = 127.0.0.0/8
mynetworks_style = host
newaliases_path = /usr/bin/newaliases
ownerrequestspecial = no
queue_directory = /private/var/spool/postfix
readme_directory = /usr/share/doc/postfix
recipient_delimiter = +
sample_directory = /usr/share/doc/postfix/examples
sendmail_path = /usr/sbin/sendmail
setgid_group = postdrop
smtpdclientrestrictions = permit_mynetworks rejectrblclient sbl-xbl.spamhaus.org rejectrblclient relays.ordb.org rejectrblclient list.dsbl.org permit
smtpdpw_server_securityoptions = login
smtpdrecipientrestrictions = permitsasl_authenticated,permit_mynetworks,reject_unauthdestination,permit
smtpdsasl_authenable = yes
smtpdtls_keyfile =
smtpduse_pwserver = yes
unknownlocal_recipient_rejectcode = 550
virtualmailboxdomains =
virtual_transport = virtual

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