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On one other note, I was accessing the admin console using https://localhost:8989
I started trying https://my_ip_address:8989 and it seems to be more reliable, but I haven't tried it long enough to know if this fixes the problem.
Do you have any antivirus/antispyware application installed (even the default windows ones) that may be killing the admin server due to it running java and opening ports for network access? Most advanced features such as heuristic detection can cause such behaviour.
I do have Norton AntiVirus, but it doesn't do any sort of heuristics or restarts to my regular webserver instances. I have probably 10 different webapps all running on really weird ports and none of them exhibit this behavior. Only the administrative Sun WebServer admin console.
Your web instances listen on ports and serve requests, the admin server in addition connects to other ports as well and invokes privileged services to do its work which can be seen as suspicious by antivirus software scanning for trojans. If the resources requested by the admin server are denied to it constantly, then it will run out of connection resources eventually and die. This is a windows feature.