Yes. That's why there are some knock-off fonts that is fully legal in the United States (apart from the name, but that's trademarks).

Note: US law (for rather obvious reasons). Europe (depending on the country) has either a design trademark or a design copyright available, which means that foundries can (in theory) control their use there (in practice, uniform worldwide licensing means they go for the lowest common denominator). Asian (mainly East Asian) IP laws does have a nuance, which means that whether a design is copyrightable depends if the purpose of the said design is utilitarian or artistic.

Yes but it's complicated because everybody knows the value is in the shapes and it's gray area... many bigger agencies will ask for special licenses just to be sure. Especially if it's a logotype where font might be majority of value.

In particular, there are plenty of examples of companies putting out bounties to rogue employees who provide evidence that a business is using unlicensed software, so it's dangerous even if you can't prove through the output of the software alone that it is unlicensed.