How to check for availability of remote server or services?

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Not sure that's a particularly descriptive subject ...
 
What we're facing here is a simple situation, but not so clear of a solution.  Perhaps this is easy and/or someone can offer me suggestions from past experience?
 
Basically, our primary web server has a link to an important, well used, web site that resides on a physically different server (we have root access to both, by the way, so configuration changes are possible).
 
When the remote web server is down/unavailable, we want the link to failover to a catch-all page that gives alternate access temporarily to important pieces.
 
The second scenario is that the remote web server itself is up, but the application running (jboss in this case) is down or non-responsive.  We want to accomplish the same thing.
 
My guess is that the first one is a lot easier than the second.  :-)  I'm not sure if #2 is as easy as creating a custom 404 page.
 
Anyways, really appreciating input and suggestions.
 
 
\\ Robert J. Granvin                                             Webmaster
 \\ robert.granvin@xxxxxxxxxxxxxx                       Metro State University

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