Hammertoes with greater preoperative transverse plane deformity are more likely to recur after corrective surgery; however, it is unclear whether this represents an inherent (fixed, non-modifiable) risk, or whether steps can be taken intraoperatively to mitigate this risk. In this study, we examined whether transverse plane transposition and/or shortening of the 2nd metatarsal during 2nd hammertoe surgery influenced recurrence. We performed a secondary analysis of pre-existing data from patients that had previously undergone 2nd hammertoe surgery at our institution between January 1, 2011 and December 31, 2013. One hundred two patients (137 toes) were followed for a mean 28 ± 7.8 months postoperatively. Thirty-seven toes required, at the surgeon's discretion, an additional/concomitant Weil metatarsal osteotomy. Magnitude of transverse plane transposition and shortening of the 2nd metatarsal, and joint angular measurements were obtained from the 2nd metatarsophalangeal joint on weightbearing AP radiographs preoperatively and at 6-10 weeks postoperatively. Cox regression analysis was used to identify predictors of hammertoe recurrence using these new variables and a set of known predictors. In the final regression model, failure to establish a satisfactory postoperative metatarsal parabola (i.e., long 2nd metatarsal; Nilsonne values < -4mm, multivariate hazards ratio [HR] 1.96, P=0.097), and intraoperative lateral transposition of the metatarsal head (multivariate HR 3.45, P=0.028) seemed to confer additional risk for hammertoe recurrence. We conclude that shortening osteotomies may be assistive in some individuals, while further inquiry is still needed to determine whether similar benefits can be derived from medial head transposition in medial toe deformities. Level of Clinical Evidence: 3, comparative study Classification: Forefoot Reconstruction.