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Presuming that ones taxes are paid timely, is it possible that one could meet only one safe harbor criterion and it not be the "smaller" amount, thus triggering a penalty? The phrase in question just seems a bit superfluous to me.

No, the first safe harbor is by definition the one with the smallest value.

There are three safe harbors. For ease, lets say their amount are X, Y and Z. Don't worry about which safe harbor they represent.

They could all be equal, but more likely they are different.
The following is true:
X <= Y <= Z

Any amount equal to or exceeding X, meets the safe harbor with the lowest value. It could be any of the three.

Any amount equal to or exceeding Y, meets two safe harbors. The lowest and the next.

Any amount equal to or exceeding Z, meets all of the three safe harbors.

The statement is meant to clarify, that the smallest amount is sufficient. If you are use to reading specifications carefully, it doesn't add any additional information.
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