Scorn appreciated and noted. 
I’ve had only ONE other person who described the symptoms you’re experiencing with BOClean. THAT person wrote to me about this since your complaint was seen on securecomp as well. When THIS person encountered it, this was the cause and the problem never recurred since for that one person.
Dunno what I can tell you would be the cause - the autoupdate and the manual update do the exact same thing in BOClean under W2K … they call the shell to run BOC4UPD (the updater) and that gets the update whether invoked by BOClean on its timer or if you open the menu and click the button. Same thing gets called the same way - only difference is one requires a click, the other receives a timeout. Same call though.
I can understand your impatience and frustration but all I can tell you is I’m as interested in ANY problem as always, but whatever’s going on there ain’t in BOClean or it would be a common event. There’s something squirrely there and I can do little more than grasp at straws with what the problem could possibly be with other people’s code. I can fix OUR stuff, but can’t do much about other people’s stuff. So let’s calm down for a minute and realize I’d like it to work for you as you WANT it to. I also realize you have experience in what we’re both doing and KNOW that when the “geeks hit the floor and stop at YOUR desktop, it behaves perfectly” and thus, you the “idiot at the keyboard, heh” are made to look like a complete fool.
Obviously you’ve been with PSC for a while and KNOW we’ve always cared … but like anyone else, we can only fix what we find. And if it’s someone else’s code, about all we can do is say “well … try this, try that, let me know.” It ain’t like I’ve asked you to “try rebooting” … or “ummm, no … that’s not supported, PLEASE upgrade your OS to something Microsoft still supports.” So this ain’t no game I’m playing, I’m literally STUMPED. Seriously! But I still want to try to help here, especially once we get 4.24 out the door and I have a wee bit less pressure than right now. 
But simple reality is that if the updater is being blocked, something ELSE is blocking it - either WININET settings, firewall policies or something else in that particular configuration. When PSC went under, we still had banks running NT3.5, NT4 and WFW3.11 with WIN32S … and BOClean even supports THOSE! But if it ain’t “offline” “pre-configured IE settings” or some other security program refusing a “child process” on that autoupdate, I’m plumb out of ideas. I wrote the code, I know what it does and what it expects and it’s designed NOT to be finicky … with all the stuff we’ve had thrown at us after all these years, anyway. Heh.