The aim of this study was to evaluate the accuracy of bone sounding (BS) in assessing the facial osseous-gingival tissue relationship (FOGTR) of failing maxillary anterior teeth. Dental records of patients who received immediate implant placement (IIP) at the maxillary anterior area were screened. Mid- FOGTR prior to extraction (BS), and immediately after flapless extraction (direct bone level [DBL] measurement) were analyzed. A total of 160 patients with 190 maxillary anterior teeth were included. The mean FOGTR obtained from BS and DBL were 3.19 ± 0.71 mm and 3.47 ± 1.29 mm, respectively (P = .004). The two measurements were identical 83.2% of the time, within 1-mm discrepancy 4.7% of the time, and > ± 1 mm discrepancy 12.1% of the time. When discrepancy was observed, BS underestimated DBL 14.2% of the time and overestimated 2.6% of the time. Though statistically significant, the correlation was weak (Pearson correlation coefficient r = .238, P = .0018). BS is an acceptably accurate and minimally invasive diagnostic tool for measuring FOGTR. However, while the mean difference between BS and DBL measurement is small (0.28 mm), the large range of difference can be alarming. Therefore, clinicians should always prepare alternative treatment options for IIP prior to extraction.