Melanoma incidence is increasing globally with Australia having the highest incidence in the world. Pregnancy-associated melanoma is recognized in the published work; however, significant knowledge deficiencies exist. We present the case of a 34-year-old woman with dysplastic nevus syndrome who over a 15-year period developed a total of nine melanomas, with eight clustered around an 18-month peri- to post-partum period. The first eight lesions were in situ with the ninth lesion invasive. No metastatic disease was observed over the 18-year follow-up period. This case identifies the potential sensitivity of a subset of melanomas to pregnancy-related factors, with particular relevance to the development of lesions in the post-partum period. We suggest that patients with a history of any documented melanoma risk factors, particularly dysplastic nevus syndrome, require close monitoring especially during pregnancy and early post-partum.