Is the resolver supposed to periodically check for updates to the
resolv.conf, or are the applications somehow caching the IP of the DNS
server?

No, resolv.conf is only read once when the resolver routines initialize.

The solution is to run a local caching nameserver instance. You should do this anyway, for performance reasons. Add 'named_enable="YES"' to /etc/rc.conf, and modify your /etc/dhclient.conf as follows:

interface "ath0" {
        supersede domain-name "orthanc.ca";
        supersede domain-name-servers 127.0.0.1;
}

interface "bge0" {
        supersede domain-name "orthanc.ca";
        supersede domain-name-servers 127.0.0.1;
}

Change the domain string to something more appropriate, and adjust the interface names to match your laptop. You'll need to start named and restart the dhclient instances (in that order) for the changes to take effect.

--lyndon
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