Background and objectives: The purpose of the study was to evaluate and compare ruler and digital planimetry methods to measure extraction socket wounds. Materials and Methods: In total, 41 extraction socket wounds were selected for assessment of wound area by ruler and digital planimetry methods. In the simple ruler method, the periodontal probe was utilized to measure the length and breadth of the extraction wound, whereas in the digital planimetry technique, Pictzar software was used. Data were analyzed using R software version 4.1.1 and Excel. For intergroup comparisons of wound surface area, Welch t-tests were used, and paired t-tests were used for intragroup comparisons. Intra-class correlation coefficients (ICC) and 95% confidence intervals (CIs) were used to evaluate the inter-method reliabilities of surface area. Results: Both ruler and digital planimetry techniques showed post-operative reductions in surface area. A significant difference was reported between the two techniques; however, the ruler method measurements were overestimated compared to those obtained with digital planimetry. Conclusions: This study concludes that digital planimetry techniques provide more accurate results when compared with the simple ruler method.