Postoperative free tissue transfer reexploration procedures are relatively infrequent but associated with increased overall failure rates. This study examines the differences between flaps requiring takeback versus no takeback, as well as trends in reexploration techniques that may increase the odds of successful salvage. A retrospective review was conducted on all free tissue transfers performed at our institution from 2011 to 2022. Patients who underwent flap reexploration within 30 days of the original procedure were compared with a randomly selected control group who underwent free flap procedures without reexploration (1:2 cases to controls). Univariate and multivariate logistic regression analyses were performed. From 1,213 free tissue transfers performed in the study period, 187 patients were included in the analysis. Of the total flaps performed, 62 (0.05%) required takeback, and 125 were randomly selected as a control group. Free flap indication, flap type, reconstruction location, and number of venous anastomoses differed significantly between the two groups. Among the reexplored flaps, 8 (4.3% of the total) had a subsequent failure while 54 (87.10%) were salvaged, with significant differences in cause of initial flap failure, affected vessel type, and salvage technique. Free tissue transfers least prone to reexploration involved breast reconstruction in patients without predisposition to hypercoagulability or reconstruction history. When takeback operations were required, salvage was more likely in those without microvascular compromise or with an isolated venous injury who required a single exploratory operation.