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My prefix is a reply

My suffix is insanity

My infix is grassy

My whole is false

There is a little joke here bonus points if you can find it

Hints

Crossreference

How many fingers am I holding up?

Monopoly money

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Perhaps the answer is

COUNTERFEIT

My prefix is a reply

A counter is a response

My suffix is insanity

Feit is pronounced as "fit", as in a fit of madness or insanity

My infix is grassy

Terf is pronounced the same as "turf", an upper layer of grassy ground

My whole is false

Counterfeits are fake

This also fits with some other clues, because

Counterfeit money will get you in trouble with the law, and another term for counterfeit/fake bills is "Monopoly money"

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  • $\begingroup$ If the infix can overlap the prefix and/or suffix that opens a lot more possibilities! $\endgroup$ – TTT Aug 28 at 21:22
  • $\begingroup$ Bingo!!!! well done $\endgroup$ – Prince Deepthinker Aug 29 at 0:05
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This doesn't fit all the clues, but perhaps some of this will help others:

kleptomania

Details:

Title: "In trouble with the law" - if you're a kleptomaniac, your're probably going to get caught stealing eventually.

Prefix: k = this just might be the single most popular reply in all texts and chats.

Suffix: mania = insanity

Infix: lepto - symptoms of the disease might be "gassy" (vomiting and diarrhea). Close enough to "grassy"? Hehe.

I don't have a match for the rest, but here are some ideas: "How many fingers am I holding up?" might refer to the book 1984, where Winston sees 4 fingers but is trying to be convinced (via drugs and torture) that there are actually 5 fingers, and the goal of this exercise is to make Winston "sane". Maybe there's a big brother reference in this puzzle somewhere? For monopoly money, when you start the game you have 1500, and the entire game comes with 20,580, in case either of those numbers are relevant somehow.

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Acknowledge?

Ack is fundamentally a reply - it is used for nothing else. There's a certain infamous grassy knoll. One might indeed stand on the precipice of insanity, on the thin ledge before the fall. I...suspect that this isn't truly the answer, because it doesn't seem to fit the rest of the riddle all that well, but it fit those first parts well enough that I wished to share. Unless the joke is that by "whole" you meant "hole", and you're saying that "allege" is false?

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  • $\begingroup$ No, wrong answer, a little hint... You need to 'acknowledge' the title of this puzzle more than what your answer suggests $\endgroup$ – Prince Deepthinker Aug 27 at 17:51
  • $\begingroup$ It seems you are unfamiliar with the comic strip Cathy, whose protagonists uses "Ack!" as an unprompted interjection pretty much all the time. $\endgroup$ – Nuclear Hoagie Aug 28 at 20:25

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