This hat was awarded on September 2, 2009 to all players who had not used external idling programs and had played at least once since the introduction of the item drop system. During the Mann-Conomy Update, the hat was dropped a second time for players who did not receive it during the initial drop. This includes those who were excluded from the first drop for using external idle programs.
- Some players have still yet to receive a Cheater's Lament from the second distribution.
- The hat description was written by AndyAML for the Hat Describing Contest.
- When players viewed their backpacks after receiving the Cheater's Lament on September 2, 2009, the following message was displayed: "Congratulations! Your honesty has been rewarded with a new hat!" The message did not appear, however, when the item was awarded to the community during the Mann-Conomy Update.