PURPOSE: To assess the effect of the shooting angle variation on linear and planimetric measurements of the pink and white tissues on intraoral photographs. METHODS: From intraoral three-dimensional (3D) scans of the anterior region in 10 patients, ninety-nine two-dimensional (2D) "scan pictures" each were generated with different shooting angles, each varying in 5° horizontal and vertical increments. Eleven intraoral photographs of each patient and tooth site were taken free-hand: one shot at baseline and 5 shots after 3 and 6 months at slightly varying shooting angles. Papilla height (PH) and area (PA) and tooth crown area (TCA) were estimated on all photographs; the "best-match-to-baseline" photograph from those taken at 3 and 6 months was chosen by 6 evaluators. RESULTS: Within the first 10° of deviation from the baseline shooting angle, measurements on the 2D "scan pictures" distorted ≤0.5 mm for PH and ≤10% for PA and TCA. Compared to baseline, only 6 out of 100 photographs presented ≥0.5 mm difference in PH, none of the TCA measurements showed distortion ≥10%, and only in 4 instances a ≥10% distortion of the PA was observed. Poor to moderate inter- and intra-rater agreement in choosing the "best-match-to-baseline" photograph was found, but photographs with clinically relevant changes were only seldomly chosen. CONCLUSIONS: Deviations in the shooting angle ≤10° from the baseline shot cause clinically negligible distortions in linear and planimetric measurements. Highly comparable intraoral photographs of the anterior maxillary teeth can be captured "free-hand" in slightly varying perspective, and then selecting the "best-match-to-baseline".