In terms of expressing the linguistic point being made, it seems like a fine analogy.

The point is, apparently, that "ask" is a euphemism for something that you are effectively obligated to do.

You're reading much too far into it.

As an English person I am finding this thread very confusing because I encounter very few situations where "ask" doesn't mean exactly what patio11 is describing.

This is especially true when the dialogue is between two people (or entities) of different social status or power, but it's also pretty rude to not oblige when you are close to the person.

The only time it is truly voluntary is when there is no relationship and nothing to lose by declining.

If the IRS would "ask" me about income in the same way that I "ask" my wife to pass me the peas when we're having dinner, you can be sure I wouldn't be paying any taxes...

Sounds more like he wasn't reading far enough into it

It’s a good analogy. It explains the word “ask” in this case means “requires”.

That was the point, it's "ask" in the sense of "we're not really asking."

No, they cannot jail you for a mistake if in fact you honestly think you did everything right. https://en.m.wikipedia.org/wiki/Cheek_v._United_States

That's not quite right. The case you cite does support your position. But, the bar for jail time is a higher hurdle for the gov't to surmount than that. You merely have a good faith belief you did not violate the law. Therefore, if you are handling a gray area and you know the IRS could take a different position, you can still rest easy about jail time so long as you don't intentionally deceive/lie/etc. This is not legal advice

The IRS even has a way for you to tell them "I think the law says this".

Also, if you and they don't find a mistake for a few years, there is a statutory limitation on them even collecting money. I don't remember exactly, but it's less that I'd thought.