I'm considering investing some time in adding additional debug output to my
version of SMTPHandler.java in order to see if I can get a better grasp of
what exactly is happening when the connection is lost, but I wonder if there
isn't a better approach?

Try running james in "run mode" (console not detached, not in background) to see the console (bin/phoenix.sh run) or to look in the temp/phoenix.console file to see if you can find exception stack trace dumps.

You could also test one of the nightly builds from here:
http://svn.apache.org/builds/james/nightly/bin/
to see if the problem is still present or not.
(look here for the configuration changes: http://wiki.apache.org/james/JamesV2)

Stefano

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