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DrJava presumes that a Java JRE is available. All Java
applications make this assumption. So the issue is how to
start the JRE (the "java" command from the command line) if
it is not installed but simply available on attached
storage. On Linux, which I know much better than Windows, I
think the issue of where Java is located would be
transparent (modulo setting some environment variables). On
Windows, you would have to run a script from the command
line to run the JRE from attached storage. I am not a
Windows hacker (we develop DrJava on Windows using Cygwin
which simulates a Unix environment) so I don't know what
gotchas are likely to arise if you try this.

DrJava is a conventional Java application with one major
exception: it has to be able to start additional Java
Virtual Machines after it starts. There is a reasonable
chance that if you develop a Windows script to run a trivial
Java application packaged as a jar file that you can run
DrJava in the same way. As long as your environment
contains a definition for "JAVA_HOME" that refers to the
correct location of java on the attached device, I don't see
why restarting should not work.

We have never pursued the issue of creating a "DrJava Live"
because every machine in our educational environment has a
recent edition of Java installed. We consider Java to be
part of the OS (as it is on Mac OSX). Most of our students
work primarily on their own machines so we instruct them on
how to install the Java SDK (a snap as long as you have
access to broadband which is readily available on campus).
My impression is that most other universities work similarly.

Our resources for DrJava development are very limited, but I
will ask a student in my development team to look at the issue.