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Venue is likely Idaho.

Under what authority or condition would a stipulation of a will be considered contested?

Will Contest. If any person shall for any reason or in any manner whatever, directly or indirectly, contest this Will in whole or in part on any ground whatever, or oppose or object to any of the provisions hereof, or seek to invalidate any such provisions, or shall seek or endeavor to succeed to my estate or any part thereof otherwise than through this Will, then I direct that such person shall neither take nor receive anything from my estate and any gift, bequest, devise or other interest in my estate to which such person would otherwise be entitled by virtue of the provisions of this Will or law, such gift, bequest, devise or other interest in my estate shall stand revoked and be cancelled and rendered void and of no effect whatever; and I give, devise and bequeath such gift, bequest, devise or other interest in my estate to those who would be entitled thereto under this Will had such person predeceased me.

What I am wondering is whom is the authority that decides if the Will is being contested? Could an executor of the will decide this? Does a judge need to decide this? Or if someone wants to make that accusation that's when we get injunctions and lawyer up?

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As a prelude, such a clause is unenforceable under Idaho law, "if probable cause exists for instituting proceedings". The grounds for contesting a will are ignoring state law, testator lacks capacity (not of sound mind), undue influence, and fraud. The case of Eggan's estate established numerous points of Idaho law regarding contesting a will, which has a focus on instructions to a jury regarding grounds for invalidating a will.

Suppose that Smith elects to contest the will on grounds of undue influence (I also assume that the will nominates Jones as personal representative). Smith has to officially petition the court, saying what the legal grounds for contesting the will are. There is a law about disputing wills, but in general the procedure is the same for all civil disputes. Smith may decide to say "It's unfair, I didn't get enough money" (that is not a legally sufficient basis for setting aside a will). Jones can petition the court to dismiss Smith's complaint. The court may decide that there are valid questions of fact or law behind the contesting petition, or they may grant the request to dismiss the petition. Dismissal basically means "there isn't enough reason to even hear this case".

"Probable cause" usually relates to criminal cases, but can be involved in civil cases such as Badell v. Beeks. It is a "judgment call", answered this way:

The question of probable cause is to be determined in the light of those facts that the accuser knows or reasonably believes to exist at the time when he acts. His subsequent discovery of exculpatory facts does not indicate a lack of probable cause for initiating the proceedings, although he may make himself liable by subsequently taking an active part in pressing the proceedings.

In this case, Jones might conclude that Smith lacked probable cause and will not distribute the required share to Smith. Smith could then sue, and there would be a trial over the legality of the non-disbursal of property. Jones has a duty to sue, as personal representative (if Jones does not sue, Doe, a beneficiary, may sue Jones). Now the court has to decide if there was probable cause. Either the judge makes that decision, or the jury does (bench trials and jury trials both exist under Idaho civil law). The court does not volunteer judgments when there is no case, so somebody has to initiate an action where the question of probable cause needs to be determined. The personal representative doesn't "decide" that, but they have to believe it to the point of filing suit (it could be anyone else with standing, like cousin Billy).

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