I've read 5 different sets of instructions for how to do this. I still can't get it to work. I send messages with sendmail -t -v. Here's the output:
NancySmith@comcast.net... Connecting to [127.0.0.1] via relay...
220 homedomain.net ESMTP Sendmail 8.14.5/8.14.5; Thu, 20 Oct 2011 20:08:19 -0600
>>> EHLO homedomain.net
250-homedomain.net Hello IDENT:25@localhost [127.0.0.1], pleased to meet you
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-EXPN
250-VERB
250-8BITMIME
250-SIZE
250-DSN
250-ETRN
250-AUTH DIGEST-MD5 CRAM-MD5
250-DELIVERBY
250 HELP
>>> VERB
250 2.0.0 Verbose mode
>>> MAIL From:<JoeJones@gmail.com> SIZE=226 AUTH=JoeJones@gmail.com
250 2.1.0 <JoeJones@gmail.com>... Sender ok
>>> RCPT To:<NancySmith@comcast.net>
>>> DATA
250 2.1.5 <NancySmith@comcast.net>... Recipient ok
354 Enter mail, end with "." on a line by itself
>>> .
050 <NancySmith@comcast.net>... Connecting to smtp.gmail.com port 587 via relay...
050 <NancySmith@comcast.net>... Deferred
250 2.0.0 p9L28JvG007207 Message accepted for delivery
NancySmith@comcast.net... Sent (p9L28JvG007207 Message accepted for delivery)
Closing connection to [127.0.0.1]
>>> QUIT
About 7 minutes elapses during the '>>> .' line.
/var/log/maillog records:
Oct 20 20:14:38 homedomain sm-mta[7207]: p9L28JvG007207: to=<NancySmith@comcast.net>, delay=00:06:19, xdelay=00:06:19, mailer=relay, pri=30473, relay=587, dsn=4.0.0, stat=Deferred
Oct 20 20:14:38 homedomain sendmail[7206]: p9L28JLk007206: to=NancySmith@comcast.net, ctladdr=JoeJones@gmail.com (0/0), delay=00:06:19, xdelay=00:06:19, mailer=relay, pri=30226, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (p9L28JvG007207 Message accepted for delivery)
Oct 20 20:21:31 homedomain sendmail[7310]: p9L28JvG007207: to=<NancySmith@comcast.net>, delay=00:13:12, xdelay=00:06:19, mailer=relay, pri=120473, relay=587, dsn=4.0.0, stat=Deferred
