This appears to have been a firewall issue. My updates to my ACL’s weren’t taking. I fixed that and am now able to download the updates.

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From: immram [mailto:immram@gmail.com]
Sent: Monday, November 19, 2007 2:53 PM
To: Boyd, Chad
Cc: macports-users@lists.macosforge.org
Subject: Re: MacPorts not updating on Leopard

On Nov 19, 2007 8:47 PM, Boyd, Chad <CBoyd@madden.com> wrote:

I have X11, XCode tools (from the Leopard disc) and MacPorts 1.5.0-10.5 installed but when I run the command:

Sudo port -dv selfupdate

I get this output:

DEBUG: Rebuilding the MacPorts base system if needed.
DEBUG: Synchronizing ports tree(s)
Synchronizing from rsync://rsync.macports.org/release/ports/
DEBUG: /usr/bin/rsync -rtzv --delete-after rsync://rsync.macports.org/release/ports/ /opt/local/var/macports/sources/rsync.macports.org/release/ports
rsync: failed to connect to rsync.macports.org: Operation timed out (60)
rsync error: error in socket IO (code 10) at /SourceCache/rsync/rsync-30/rsync/clientserver.c(94)
DEBUG: Couldn't sync the ports tree: sync failed doing rsync
   while executing
"macports::selfupdate [array get global_options]"
Error: /opt/local/bin/port: selfupdate failed: Couldn't sync the ports tree: sync failed doing rsync

are you running PeerGuardian? try disabling it and see if it works...