Teacher education assumes that the more time observing practising teachers, the better, but the value of observation (guided or unguided) in early field experiences is unknown. In this mixed-methods study, we examined the levels of reflection, use of future-oriented reflection, and changes in the reflective writing of 90 preservice elementary education teachers enrolled in two sections of an early field experience course (one of which received guided observation) at a large university in the United States. While the level of reflection in the writing of 35% of the preservice teachers (PTs) increased in complexity over the span of a semester, only 10% of the PTs ever demonstrated the deepest level of reflection in their writing. Future-oriented reflection accounted for 6% of the language in the assignments, with a majority of the instances documenting what PTs planned to do in their future classrooms. PTs in the guided observation group demonstrated a significantly higher level of reflection than those in the unguided group. With these findings in mind, we present implications for teacher-education field experiences and future research, such as providing scaffolding for future-oriented reflection.