Background: Previous research indicates that reflection can foster medical communication competence. However, best practices for embedding reflection in online medical education are missing. This study examined how reflection processes can be promoted and embedded in an e-learning course on physician–patient communication to foster learning. Methods: We investigated three differently designed e-learning conditions featuring different proportions of reflection triggers and compared their effects on students’ reflections. We had 114 medical students in their first clinical year complete one of the variants: video modelling (VM, n = 39), video reflection (VR, n = 39), or a variant merging both approaches (VMR, n = 36). Each student wrote a total of nine reflections based on the same guiding questions at three time points embedded in the course. The students’ levels of reflection were measured using an adapted version of the REFLECT rubric (scale 0–18). Results: Students of all course variants achieved good levels of reflection beyond the descriptive level at all three time points, with no significant differences between the variants. The mean reflection scores at the end of the course were M = 14.22 for VM (SD = 2.23), M = 13.56 for VR (SD = 2.48), and M = 13.24 for VMR (SD = 2.21). Students who completed VM showed significantly improved levels of reflection over the course, whereas we found no statistically significant development for those in VR or VMR. The reflection scores correlated significantly positively with each other, as did the text lengths of the written reflections. Reflection scores also correlated significantly positively with text length. Conclusions: Our study offers a teaching strategy that can foster good levels of reflection, as demonstrated in the three e-learning variants. The developed reflection prompts can be easily embedded in various e-learning environments and enable reflections of good quality, even in settings with limited available teaching time.