Leaving a message with Butterbur was a bad idea, I don't know if that fits under the original question or not, but still, a bad idea. Somewhat surprising too, considering Gandalf's track record of character judgment (minus the Sauraman snafu). Not that Butterbur's character was bad, but the element of his character that Gandalf counted on was deficient in a most obvious sense, it's like asking a clepto to watch your stuff while you see a man about a horse.
Also, and perhaps more suited to the question, although the context clearly removes my forthcoming example from its, just claimed, position of being suited, when Gandalf says it would be better if Pippin would have taken the plunge into the ol' Moria well.
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War Eagle.
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