I've got this setup and works great....if the message is small. However for messages that take longer than 60 seconds to go through it fails.

Taking a look at /var/log/mail.log I see this.

Code:
pr  2 17:45:16 macbook postfix/master[874]: daemon started -- version 2.4.3, configuration /etc/postfix
Apr  2 17:45:16 macbook postfix/qmgr[876]: 582AB11E853: from=<REMOVED>, size=7373120, nrcpt=1 (queue active)
Apr  2 17:45:17 macbook postfix/smtp[879]: setting up TLS connection to smtp.googlemail.com
Apr  2 17:45:17 macbook postfix/pickup[875]: 4858811EDBC: uid=501 from=<pthomas>
Apr  2 17:45:17 macbook postfix/cleanup[877]: 4858811EDBC: message-id=<20080402224516.GA870@macbook.philzy.com>
Apr  2 17:45:17 macbook postfix/qmgr[876]: 4858811EDBC: from=<REMOVED>, size=427, nrcpt=1 (queue active)
Apr  2 17:45:17 macbook postfix/smtp[879]: Verified: subject_CN=smtp.googlemail.com, issuer=Thawte Premium Server CA
Apr  2 17:45:17 macbook postfix/smtp[879]: TLS connection established to smtp.googlemail.com: TLSv1 with cipher DES-CBC3-SHA (168/168 bits)
Apr  2 17:45:17 macbook postfix/smtp[881]: setting up TLS connection to smtp.googlemail.com
Apr  2 17:45:17 macbook postfix/smtp[881]: Verified: subject_CN=smtp.googlemail.com, issuer=Thawte Premium Server CA
Apr  2 17:45:17 macbook postfix/smtp[881]: TLS connection established to smtp.googlemail.com: TLSv1 with cipher DES-CBC3-SHA (168/168 bits)
Apr  2 17:45:19 macbook postfix/smtp[881]: 4858811EDBC: to=<REMOVED>, relay=smtp.googlemail.com[72.14.247.16]:587, delay=3.1, delays=1.1/0.01/0.94/1, dsn=2.0.0, status=sent (250 2.0.0 OK 1207176319 8sm2864020agd.30)
Apr  2 17:45:19 macbook postfix/qmgr[876]: 4858811EDBC: removed
Apr  2 17:46:16 macbook postfix/master[874]: master exit time has arrived
The only place that I see a 60 second timeout value is in /etc/postfix/master.cf on the line related to "pickup". I changed that to 6000 and tried again but got the same result. Also rebooted the MacBook and no love there either.

Any suggestions?