Once controversial or cutting-edge, freewriting has recently become "part of every writing teacher's repertoire" (Bizzell and Herzberg in Elbow 393). On par with outlining or webbing, freewriting seems to be a go-to practice in a writing teacher's tool kit. This downshift into uncritical acceptance presents an apt moment to reconsider how we implement freewriting practices in the college writing classroom. Toward this reexamination, this essay problematizes the pervasive assumption about freewriting that it is above all else "easy, effortless, quick, and free from judgment, hesitation, and doubt". The essay suggests that this assumed ease remains one of the thorniest and obscured problems in the practice of classroom-based freewriting and hypothesizes that the mode required to freewrite is not necessarily natural or automatic for student writers, but rather requires training, conversation, and reorientation. In order for freewriting to be an effective means of stimulating critical and creative thinking, teachers of writing need to consider not only how we can add in analytical and reflective thinking "about" freewriting texts, but also how we can get students to do productive, questioning, and exploratory thinking "within" freewriting itself. Above all, facilitators of freewriting can benefit from assuming the difficulties of thinking through freewriting. (Contains 2 figures and 6 notes.)