I wouldn't recommend using external: in Bundle-Classpath. It's Equinox-specific and therefore isn't governed by the OSGi standard. There's no guarantee that it'll work in dm Server or that, if it works now, that it will continue to work in the future. Also, as the jar file is outside of a bundle, it's excluded from OSGi's lifecycle management. If anyone changed, moved, or deleted the jar file, you get all sorts of unexpected and unpleasant problems.
Now, to answer your question. The contents of the Jar will be loaded multiple times: once for each bundle which references it, using the bundle's classloader. I really wouldn't recommend using it though!
Andy Wilkinson
SpringSource