Board Thread:The Quarters - Q & A/@comment-216.15.56.90-20140404014623/@comment-24150802-20140404021226

The Pickpocket skill is described in detail here: http://habitrpg.wikia.com/wiki/Rogue

Note this part: "If the task value is negative, "-1" is used instead of its value." Task values are described here and it shows that to-dos (yellow to dark red) can have values from 1 to -1 and below (i.e., more negative). But all the negative values are treated as -1 by Pickpocket, so there's no additional advantage to casting the skill on a dark red to-do. In fact, you'll get slightly more reward for casting it on a new yellow to-do (value +1). But blue dailies and habits are far better.