The concept of the “careful habit”[i] is intriguing. The law of evidence vigorously distinguishes between character evidence (largely inadmissible)[ii] and habit evidence (presumptively admissible).[iii] Character is understood as a propensity to act in a certain fashion[iv]—a person’s disposition. Habit is understood as non-volitional, repetitive specific conduct, in response to stimuli, over a rather lengthy period of time.[v] “Carefulness” is known by the law as a character trait.[vi] Carefulness should not be confused with habit, yet this confusion has occurred in multiple jurisdictions, many years ago and recently. This paper seeks to explore the development of the curious and anomalous concept of the “careful habit” in the law of evidence and, ultimately, recommends its elimination. [i]See e.g., Powell v. Dean Foods Co., 7 N.E.3d 675 (1st Dist. 2013). [ii]Fed. R. Evid. 404. [iii]Fed. R. Evid. 406. [iv]See Sharpe v. Bestop, 730 A.2d 285 (1999). [v]Id. [vi]See Woodson v. Porter Brown Limestone Co., 916 S.W.2d 896, 908 (Tenn. 1996) (referring to “trait of carefulness”); Ring v. Rogers, 927 P.2d 152, 153-54 (1996); State v. Higbie, 847 A.2d 401, 402, 404 (2004); State v. Enakiev, 29 P.3d 1160, 1163 (2001).