He has announced that the current state of cert revocation will be covered in detail on the next upcoming episode of Security Now. The current page is wordy and lacking, and I will be very surprised if he doesn't update it with real substantiating information soon.
Just about everything he writes is MASM. He talked once briefly about a custom packet rewriter that sits on his edge to assure that any packet reaching GRC or his internal network is properly formed. He didn't divulge much else about it.
He did take up Javascript a couple years ago because of a new-found value in client-side processing and canvas[1] for animation.
He's currently working on SpinRite 6.1 with modern I/O support and an authentication mechanism he came up with out of the blue called SQRL[2].
He's definitely adamant about the ongoing exclusion of raw sockets on Windows and alleges malware would absolutely abuse it if it were available. He still talks about it once and a while and certainly does not regret that stance.
> Will you prefer a long wait and then silently back on prompt or an indication of something happening?
This is what the -v, --verbose option is for. Without this flag, you should assume everything is operating as expected until you receive an error message or an exit status >0.