I think the way it occurred was that I had a dual-boot machine (WinXP/Ubuntu 
8.04) that had originally signed up for the lease under Windows, then was shut 
off and booted into Linux, where it couldn't connect, then booted back into 
Windows, where I observed the issue while diagnosing.

The option had not yet been set to instruct Windows machines to drop the
lease when shutting down, so it may simply have been that the lease was
still active. It does not seem to be happening now -- booting in either
mode gets the desired assignment.

I don't really want to attempt to reproduce it since I have everything
working the way I want it to now, but I wanted to report this since the
DHCP dialogue seemed strange. If I find a way to reproduce it, I will
report back.

-- 
DHCP Request Cycle can get caught in infinite loop
https://bugs.launchpad.net/bugs/327703
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