There's a lot of what you say that sounds familiar, like the TiVo being
able to do its network test when I can't even ping it, but also a lot
that doesn't match my problem, like I've never noticed the SqueezeBox
failing to work, and I definitely don't have separate MAC addresses. 
What firmware is your SqueezeBox running?

I have found that if I manually put my SqueezeBox and the TiVo in my
computer's ARP table with the same MAC address, then everything seems
to work just fine.  Of course, that's less than optimal for many
reasons.

I just did a network snoop and determined that I'm just not getting ARP
replies when the device connections fail, sometimes for either device. 
The most recent test I did, the only reason my computer got the
SqueezeBox's MAC address is because it did an ARP request requesting my
computer's MAC address.  God knows why it did that.  It requested the
MAC address of the SlimServer computer (which is separate from the
computer I'm working on) first.  I have other devices on the wireless
network that respond to ARPs properly, so I don't think it has anything
to do with my access point, although it's possible that there's more to
it than just that.


-- 
wfaulk
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