I'm not sure what exactly you trying to achieve, but debugger should be activated on some event (exception, break point or something), after it's activated, for example you can have a thread that create an exception and after get control back check the variable.
In debugger you can set a break point with command, see this guide, what will change the parameter.
I hope that this answer your question, if not please clarify the question.
In case of break point with command the application will be break and will continue execution without human intervention, i don't know any way how debugger can do something without application stops execution.
Just a thought, are you sure you need debugger for this? Can't you just use registry for that and use this to get notification about registry change.