You'd have to use KGDB for the kernel-space debugging, and GDB for the user space debugging. So, yeah, it's like debugging two programs, but each needs its own debugger. The only debugger I know that can handle both at once is proprietary -- the Arriba debugger from Viosoft, but I don't know how many architectures they support. The target mostly embedded systems, esp. MIPS.
-John
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