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I know it is possible to remotely debug code using gdb’s server mode and I know it is possible to debug code that has been cross-compiled for another architecture, but is it possible to go a step further and remotely debug Linux applications from OS X using gdbserver?
Certainly, but you need a cross-compiled GDB, compiled for OSX-host and Linux-target. This is not at all uncommon; there should be plenty of GDB documentation to cover this.