Cannot send voicemail attachments

I am trying to send voice mail email notifications w/ attachments, and it is not working. Here is the log from sendmail:

Feb 25 10:42:56 tmob-pbx sendmail[26319]: m1PGguNv026319: from=, size=10094, class=0, nrcpts=1, msgid=, proto=ESMTP, daemon=MTA, relay=trixbox1.localdomain [127.0.0.1]
Feb 25 10:42:56 tmob-pbx sendmail[26318]: m1PGguks026318: to="Ken Salter" , ctladdr=asterisk (102/103), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=39920, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (m1PGguNv026319 Message accepted for delivery)
Feb 25 10:42:57 tmob-pbx sendmail[26321]: STARTTLS=client, relay=mail.targetedtechnologies.com., version=TLSv1/SSLv3, verify=FAIL, cipher=AES256-SHA, bits=256/256
Feb 25 10:44:20 tmob-pbx sendmail[26069]: STARTTLS: write error=syscall error (-1), errno=104, get_error=error:00000000:lib(0):func(0):reason(0), retry=1, ssl_err=5
Feb 25 10:44:20 tmob-pbx sendmail[26069]: m1PEMC2W017265: SYSERR(root): timeout writing message to mail.targetedtechnologies.com.: Connection reset by mail.targetedtechnologies.com.
Feb 25 10:44:20 tmob-pbx sendmail[26069]: m1PEMC2W017265: to=, ctladdr= (102/103), delay=02:22:07, xdelay=00:05:01, mailer=esmtp, pri=427846, relay=mail.targetedtechnologies.com. [69.85.201.155], dsn=4.0.0, stat=Deferred
Feb 25 10:44:20 tmob-pbx sendmail[26069]: m1ONXmJQ004368: to=, ctladdr= (102/103), delay=17:10:32, xdelay=00:00:00, mailer=esmtp, pri=1749460, relay=mail.targetedtechnologies.com., dsn=4.0.0, stat=Deferred: Connection reset by mail.targetedtechnologies.com.

Notice that after sendmail connects to my mail server, after 5 minutes is disconnected by the mail server. It is as if sendmail is not sending anything and is just opening a connection.

Any thoughts? I have run setup-mail and put in my domain, and set the mail relay in the /etc/mail/sendmail.mc to my mail server (and run make -C /etc/mail and restarted the service), and I have put the IP of my PBX in my mail servers allowed relay list.