Effective file management is central to coordination in collaborative work, as shared files serve as the primary medium through which collaborators exchange contributions. Building on existing PIM and CSCW literature on file management breakdowns, we recontextualize such breakdowns within specific dynamics of collaboration. In Study 1, we conducted a need-finding interview(N=33) and identified four recurring breakdowns in collaborative file management: ambiguous file placement and ownership, inefficient version management, uninterpretable metadata, and missing status cues. Building on these findings, Study 2 used a design probe evaluation(N=12) to examine potential benefits and concerns associated with supporting collaborative file management. Participants reported benefits such as clearer ownership, stronger reference convergence, improved metadata interpretability, and heightened progress visibility, while expressing concerns related to surveillance, exploration containment, overdisclosure, and social pressure. Taken together, the studies reframe well-known file management issues as a dichotomy between perceived benefits and concerns, thereby outlining design directions for file-level alignment.