Pregnancy–associated melanoma is increasingly gaining attention in the literature, however significant knowledge deficiencies exist. The case is presented of a 34-year-old woman with dysplastic naevi syndrome who developed a total of nine melanomas over a 15-year period, with eight clustered around an 18-month peri to postpartum period. The first eight lesions were Clarke level one with the final lesion Clarke level two. No metastatic disease was found in the follow-up period until early 2016. This case identifies the sensitivity of a potential subset of melanomas to pregnancy related factors, with particular interest to the development of lesions in the postpartum period. This case suggests patients with notable risk factors require close monitoring particularly during pregnancy. Furthermore this case highlights the importance of close ongoing vigilance postpartum.