This qualitative multicase analysis investigated the role of "educational niceness" and "neutrality" (e.g., Baptiste, 2008; Bissonnette, 2016) in preservice English teacher feedback on sociopolitical issues in student writing. As part of the field experiences for several ELA methods courses at two universities, one urban and one rural, the teacher-researchers used Google Docs and other technologies (e.g., screencasts and Google Community) to connect preservice teachers (PSTs) with high school writers at a geographical distance so that urban-situated PSTs could mentor rural-situated writers and vice versa. Five methods courses over two semesters served as cases, and 12 PSTs from those courses participated in focus groups. Data included audio recordings of nine focus groups and PSTs' digital responses to student writing. Using thematic analysis, the authors explored how PSTs responded to sociopolitical perspectives in students' writing -- both engaging them and staying neutral. Although authentic opportunities for responding to student writers supported PSTs' critical reflection on teaching writing, analysis of PSTs' responses indicate that such authentic practice may not be sufficient for preparing PSTs to navigate sociopolitical issues and may, in fact, exacerbate PSTs' impulse to enact educational niceness.