or perhaps BlackICE

Wow haven't read that name since around 2000, gave me a weird feeling in my brain.

Here's another one: F.O.S.I.

It's a tvery similar concept and presentation

Is zonealarm still alive?

Portmaster has been filling this role for me for the last couple years.

I used Portmaster too until they started locking existing features behind paid subscription. And generally just the push towards microtransactions in general. I vastly prefer buy once or buy per major version.

Windows firewall control

This only prompts you after the connection has already been rejected, instead of holding it for approval like Little Snitch and Portmaster -- but I did have WFC installed on my Windows machines anyway, it's still useful.

More than a decade ago, I tinkered around with doing stuff like this. I found that many Windows apps got ugly and naughty when you hold up the connection. I started making a list of the various methods I used to try to hold the connection before user authorization could occur and that's about where I gave up on working it.

My least favorite are the games using bespoke UDP connection protocols. They try different ports so rapidly you can't approve one before they've tried fifteen more. They don't retry, so you better catch up!

It reminds me more of the old Windows firewall/IPS/IDS called Sygate. It was ahead of its time. I think Zonealarm came after since that is what I replaced it with after Symantec(?) bought Sygate and rolled the best functions of Sygate into their Professional firewall for a premium price. Sygate was free or you could buy a permanent license for a one-time fee. It was the best personal protection products available for pcs running Windows up to WinXP.

I had also tried a different firewall/privacy tool from a company in Canada I think called ZeroKnowledge. That was a great product that also allowed you fine-grained access to and control of all connections to/from your Windows pc. They had a product available for a short time but shut down suddenly. I think I read that they were bought out by another firewall company but can't remember which one. They may have been rolled into the Blackberry software line.

Both of these were available in the 90's lead-up to the dot com bust if I remember right. Sygate became obsolete when support ended around the time WinXP faded. ZeroKnowledge disappeared much earlier. I may have old executables and installers somewhere on antique backups.

Personally I used Kerio Personal Firewall. I remember it being very good and while I didn't care about outbound connections much back then, I'm pretty sure it had a similar feature it was just off by default

Yes