Postmortem interval estimations can be complicated by the inter-individual variation present in human decomposition. Forensic entomologists may especially face challenges interpreting arthropod evidence in scenarios that are not “by the book”, or that vary in unexpected ways. Therefore, it is important to report instances where blow fly colonization does not align with expected soft tissue decomposition as blow fly larvae are often used to produce a time of colonization (TOC) estimation to infer a minimum PMI. We followed the decomposition and blow fly activity of three human donors at the Anthropology Research Facility (University of Tennessee). Delayed oviposition occurred on one donor 115 d post-placement, whereas two donors experienced blow fly re-colonization after cessation of the consumption phase, one 22 d and one more than 200 d after blow fly larvae were last observed. A null hypothesis model tested whether the entomological TOC and anthropological total body score (TBS) estimations encompassed the time of placement (TOP) for each donor. While the null hypothesis was rejected for all TOC estimations, it could not be rejected for the TBS estimations. We discuss how the non-linear nature of human decomposition can pose challenges to interpreting blow fly evidence and suggest that forensic entomology practitioners should recognize these limitations in both research endeavors and applied casework.