Guides & explainers

No one certifies software the way they certify food. Here is the standard worth applying instead, and the questions that separate a filtered AI from one that merely promises to behave.

Most school filtering protects a machine. Students do not use one machine. The difference between filtering a device and filtering an account decides whether your rules survive contact with real life.

The choice is not between AI and no AI. It is between AI you can see and AI you cannot. Here is how to think it through without pretending either extreme works.

Most AI policies fail in the same two ways: they are written as prohibitions nobody can enforce, or so vaguely that no teacher can apply them on a Tuesday. Here is a structure that avoids both.

"Safe for kids" is a marketing phrase, not a specification. These are the six things worth checking, and what a good answer looks like for each.

The answer is neither yes nor no, and anyone giving you a one-word answer is selling something. Here is what ChatGPT actually refuses, what it does not, and what that means for your child.

The AI conversation in a yeshiva is not the same conversation as in a public school. The concerns are different, and so are the workable answers.

Vendors describe filtering as if it were one thing. It is at least three, they fail in different ways, and the differences decide what your students can actually get to.

Of everything schools might teach about AI, one habit outlasts the rest: checking. Here is a way to teach it that takes a single lesson and actually sticks.

Demos are built to look impressive. These twelve questions are built to find out what happens when nobody is watching — with the bad answers listed next to the good ones.

Every school that has leaned on an AI detector has eventually accused a student who did nothing wrong. The failure is not a bug in a particular product — it is the whole idea.

The useful question is not whether your child uses AI for homework. It is whether the thinking still happened. Here is how to tell.

Every filter has a miss rate above zero. What separates schools is not whether something gets through — it is what happens in the following hour.

Set a limit, then test it after it should have expired. A surprising number of advertised time controls are decorative.

A student blocked from discussing a subject who can generate a picture of it has not been protected. They have been redirected — and this is the most common gap in filtered AI products.

The phrase is doing a lot of work and means different things to different people. Here is what it can reasonably mean, what it cannot, and how to judge a tool against it.

A text rule is written in words and a modesty standard is about what appears in a picture. Those are different problems, and most products only solved the first.

Most AI guidance for schools is either abstract principles or a product pitch. This is the sequence of decisions an actual school faces, in the order they come up.

Most failed rollouts fail the same way: everything at once, in week one, with no way to fix a problem quietly. Here is the sequence that works instead.

Parents are not opposed to AI in school. They are opposed to finding out about it afterwards. Here is what to say, and a letter you can adapt.

Most advice for teachers is either breathless or defensive. This is a working list of what saves real time, what does not, and how to spot the difference.

This is where AI has the most to offer and the least written about it. The question is always the same: is the tool removing a barrier, or removing the task?

Not "use AI to write an essay". Twelve activities where the tool does something genuinely useful, several of which teach students to distrust it.

Guidance written for schools with an IT department is not much use when the IT department is whoever last fixed the printer. This is the smaller version.

The conversation matters more than the settings. Here is what to say, roughly when, and what to do when they ask whether it is alive.

You do not need technical knowledge to make good decisions about these tools. You do need one accurate mental model, because the right one predicts every failure you will see.

Every term you are likely to meet in a vendor conversation, defined plainly, with a note on why it matters rather than only what it means.

"We take your privacy seriously" tells you nothing. Here is what actually happens to the text, and the four questions that produce real answers.

A weekly window is straightforward. Yom Tov is not, and neither is a family three timezones from the server. Here is what a scheduling feature actually has to handle.

You have found something you were not meant to find. What happens in the next twenty minutes determines whether you learn anything, or only that they get better at hiding it.