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Objective. This study is aimed at determining two main points. First, if the Canary System™ (CS), initially used to assess caries, can measure a decalcification depth of bleached enamel quantitatively, and second, whether or not whitening has a harmful effect on enamel. This device can be considered a useful tool in the clinical assessment of the progression of demineralization after bleaching. Materials and Methods. This study collected sixty human premolars that are in a good state recently extracted for orthodontic reason. To properly disinfect and preserve the premolars, they were stored in a saline solution and later in distilled water for a period of two weeks to allow the premolars to rehydrate. Later, 24 hours before the experiment, the premolars were introduced into a solution of artificial saliva to acquire back their minerals. The mineral content of the teeth was measured by the Canary System™ before bleaching. The teeth were bleached with 30% hydrogen peroxide (fläsh HP 30%), 30 min per week and for 3 consecutive weeks to simulate the conditions of strong bleaching in the clinic. The extent of demineralized enamel was measured by the Canary System™ at three points on the enamel surface of each tooth. The data were averaged for each application of the bleaching product. The demineralization extent of the teeth was measured by the Canary System™ before and after bleaching. The significance level was set at 0.05, and SPSS version 26 was used. The data were analyzed by using Wilcoxon’s and Student’s tests. Results. Mineral loss occurred after the first bleaching session; the Canary System™ detected a decalcification in the first bleaching session ( 532 ± 322 μm) compared to the other sessions ( p ≤ 0.05 ), while no significant change was detected between the second and the third sessions ( p > 0.05 ). Conclusion. Based on the findings of the present study, under in vitro conditions, it was possible to measure the demineralization extent of bleached enamel with the Canary System™.