Hello,
Without more details, I can only take a guess at some potential causes. One is that the debugger did not properly remove some emulator resources in use before the next script tried to start the debugger again and use the same resource. Another is that target was left in a bad state and did not have a chance to recover. One suggestion is to try adding a target and emulator reset or power cycle of the target between each script run.
Unfortunately the diagnostic capabilities of CCScripting is very limited so it will be difficult to understand what exactly is the problem (something we addressed with the newer scripting utilities)
ki