I had a problem rather like this, and it turned out to be a fault with my router. It showed up first on one of my two Chumby Classics, which just wouldn't reconnect in the same way as the other one did.
The router fault was intermittent, so most devices worked almost all of the time, especially since most devices will successfully reconnect after dropping a connection. It eventually got sufficiently worse so as to make the problem plain - my computer would only connect to a site if I typed the site's numerical IP address.
I don't know if the router is your problem, but it may be something to consider. My experience shows that router problems can be not exactly obvious at the start, and that they may show up on Chumby first, while other devices seem OK.

Another user here with a Chumby Classic using wired ethernet that drops its connection almost once a day and requires a reboot to get it back.

I have my Chumby at work and a few months ago set an alarm to switch it to "night" mode at 17:30. The problem began around the same time, but it could simply be a coincidence. Removing the alarm has not fixed the problem.

I can tolerate the daily reboot, but it's a little annoying. In case it makes any difference I'm using an Apple USB=>Ethernet adaptor, of the type they sell for use with the MacBook Air.

Just thought I'd add another data point.

I have two Classics and a Chumby One, all on wired ethernet. The One used to drop its connection often, which was a problem because it is my bedroom alarm clock. I swapped its Belkin adaptor for the Netcomm adaptor that one of the Classics was using, and everything seems to be fine now.
I don't know why this should be so.
Possible reasons may be:
1) it was actually the connection between the adaptor and the lead in the bedroom that was bad. Swapping adaptors just resulted in the replacement adaptor being more firmly pushed into place;
2) the Classic that is now using the ex-bedroom Belkin adaptor is actually dropping its connection just as much as the One did, but because of the location of this Chumby I just don't notice it;
3) there is some aspect of the Netcomm adaptor that makes it either all round better, or better adapted to work with the One, or better adapted to work with the VPN router that the One (but not the Classic) is connected to...
Just to be clear, none of the ethernet adaptors appears to be faulty - I haven't replaced any, just swapped them around.

We host our DNS at easyDNS.  The servers themselves are hosted at Amazon.

I'll see if we can have someone look into it.

Yep, something's wrong.  There seem to be intermittent connection problems to the servers.  I'm seeing it too - it's not happening consistently, though.

Unfortunately, we can't do anything before tomorrow, due to the holiday.

Duane,
Thanks for your response. And here's hoping there's an easy resolution tomorrow.

Happy Turkey Day!

Well glad to know it's not just me. My Chumby One has been acting freaky all day: sometimes connected, sometimes not; sometimes it says it's not authorized (even though it is); able to connect to Wi-Fi but not the Chumby servers.

I appreciate your response on a holiday, Duane.

Now both of my Classics are fine, but the One still can't download the control panel.

We've isolated the problem to a load balancer at Amazon AWS.  For any given DNS fetch we get four IPs in random order - one of the four is bad.  It basically means that you have a one-in-four probability of getting a bad IP for a chumby.com domain.

Unfortunately, that means that we can't fix this directly - we'll have to open up a ticket with Amazon.

Thanks for getting this fixed, Duane. It's working good for my chumbys now.