You're hugely misreading my intentions. I'm an engineer: I see something unexpected, I want to figure out what's happening. You and I are both using the same software and you're seeing problems that I didn't even know affected some people. I'm not saying "this works for me so I don't know what you're complaining about". I'm saying "huh, this works for me. I wonder what's different between our systems? Is this something that's going to spontaneously start affecting me if I click the wrong toggle somewhere?"

Obviously the problem is possible. It's happening to you. I'd like to find out why so that I can troubleshoot and fix the problem if it starts happening to me or my friends or coworkers. And really, I'd like to help you fix it, too, if I could figure out what's causing it.

Apologies for misreading you, I'm just frustrated and accepted the fact that it is by design.

I been reading other comments and as someone (xrisk) pointed out that it is Homebrew Casks which it made sense since all of the gatekeeper alerts is coming from 'Cask-ed' apps. I could disable Gatekeeper but I rather not because MacOS is not my daily driver. I rather to keep Gatekeeper active to protect itself from moronic me.

Given how ubiquitous your problem is, I would be suspicious that security alerts are going off because you have a real security problem. I've seen similar problems when a piece of malware keeps trying to inject itself into various things, and Gatekeeper is catching it. The variety of places where you're getting alerts is a testament to the persistence of the malware, and not the fact that everything is actually broken.

That's OK. If I were in your boat, I'd probably be pretty frustrated.

Does the method of right-clicking on an app, then "Open", in Finder work to tell Gatekeeper to quit complaining?

Probably the simplest thing then would be to alias brew install to something like spctl —master-disable; brew install $1; spctl —master-enable

`spctl --master-disable` requires root permissions (sudo).

You could edit sudoers so the command doesn't require a password. But really, at that point I'd just leave Gatekeeper off.

Is it possible you do this on a corp machine that has Google's Santa running & it's just a language precision issue? Google Santa will definitely prompt on nearly everything & is extremely annoying for Homebrew. Google Santa != Gatekeeper though.

Because if they can’t reproduce, then much more likely than not, the problem is not inherent to the platform. In this case, there’s probably a deviation in config settings.

Additionally if they can’t reproduce, they can’t offer any advice or help.

It’s highly unlikely that MacOS behaves specially for your existence.

The latest time I had a Homebrew package fail to install, due to security restrictions that work just fine for the other thousands of packages there, it was the package trying to do something it shouldn’t have, and was promptly fixed. You may have run into a similar scenario.