Rules FAQ
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A character "gains" or "loses" a challenge icon whenever a card effect specifically uses that phrase. If a character stops gaining a challenge icon (for instance, due to an effect like "Off To Gulltown" expiring), that character is not considered to have "lost" that icon, and vice versa.
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Scorpion Knight can react any time a character loses an instance of any challenge icon, even if the overall calculation for that character having (or not having) that icon has not changed. For instance, if Confinement is played on Hot Pie, Scorpion Knight can react 3 times. The same if Confinement is played on a character that previously had multiple instances of an icon.
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Scorpion Knight can react to the effects of Imprisoned, Attainted and Condemned, but only immediately after they are first attached (or immediately after they regain their text box if they have somehow become blank).