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Many social media sites permit users to delete, edit, anonymize, or otherwise modify past posts. These mechanisms enable users to protect their privacy, but also to essentially change the past. We investigate perceptions of the necessity and acceptability of these mechanisms. Drawing on boundary-regulation theories of privacy, we first identify how users who reshared or responded to a post could be impacted by its retrospective modification. These mechanisms can cause boundary turbulence by recontextualizing past content and limiting accountability. In contrast, not permitting modification can lessen privacy and perpetuate harms of regrettable content. To understand how users perceive these mechanisms, we conducted 15 semi-structured interviews. Participants deemed retrospective modification crucial for fixing past mistakes. Nonetheless, they worried about the potential for deception through selective changes or removal. Participants were aware retrospective modification impacts others, yet felt these impacts could be minimized through context-aware usage of markers and proactive notifications.