This item 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, it was distributed a second time for players who had not received it during the initial drop. This second distribution also included players who were excluded the first time for using external idling programs. There is much speculation surrounding its release; however, there has been no confirmation or announcement relating to the item from Valve at all.
- Some eligible players have still not yet received 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.