Cxbx-Debugger does not work with multi-xbe titles - it just ends debugging session when game switches to another xbe.
Test-case: The Elder Scrolls III - Morrowind.
@PatrickvL Here's an idea, use existing message ID_GUI_STATUS_KRNL_IS_READY listener to send a message to debugger. Then Cxbx-Debugger will continue to work with multi-xbe titles.
A cheap fix is just to relaunch the debugger -
with the patch
bool Debugging{ false };
g_EmuShared->GetDebuggingFlag(&Debugging);
if (!CxbxExec(Debugging, nullptr, false)) {
CxbxKrnlCleanup("Could not launch %s", XbePath.c_str());
}
There's a monitoring thread that cares about this process though
With above suggestion, I do see design flaws such as...

P.S. Ignore build info since I was doing some test with tags in the past.
In summary, cxbxr-debugger isn't multi-xbe compatible design wise at the moment. Unless there is some sort of bug with monitoring thread in cxbxr-debugger?