||Failing Miserably, If Not Inventively|
I was about to suggest using the built-in auto-dial and auto-hangup feature of Eudora, but I see Apple has removed access to it in OS X. My knee-jerk reaction is that this is probably a good thing (tm), but that's based on having provided tech support for OS9 users, and so often watching the Location Manager get thrown into disarray.
I haven't bought panther yet and this "feature" of automatically softening the control a user has on their computer bodes ill for the future if it becomes a design philosophy. The horror that was Windows ME is the end product, IMHO, of catering to the newbie by hiding anything complicated and making the system "helpful" to the user a la Mr. Clippy. A better design for the behavior described above would be to ask the user, if they have clicked on "cancel" while dialing up, whether they want to turn off their auto-dial feature and leave it at that.
I'm worried about the future of networking in OSX, since I've had to put up with a similar problem in Jaguar where lookupd on my powerbook decides unpredictably on waking-from-sleep to ignore the resolv.conf and stop listening to it's own named (BIND) daemon. Since I use a lot of CNAME aliases to the localhost to develop web sites on it, this means that apache will fail, on restart, to resolve the test servers it's hosting, and the local "search" domains are ignored. I find I have to change location, change it back, and restart apache if I'm zinged by this "feature".
There's probably a better way of fiddling with the lookupd configuration to prevent this from happening, but I've never had the luxury of time to look into it. My hope is that Apple will start adding more rigid and transparent control over network configuration.