Background Tinnitus is often described as the phantom perception of a sound and is experienced by 5.1% to 42.7% of the population worldwide, at least once during their lifetime. The symptoms often reduce the patient’s quality of life. The TrackYourTinnitus (TYT) mobile health (mHealth) crowdsensing platform was developed for two operating systems (OS)—Android and iOS—to help patients demystify the daily moment-to-moment variations of their tinnitus symptoms. In all platforms developed for more than one OS, it is important to investigate whether the crowdsensed data predicts the OS that was used in order to understand the degree to which the OS is a confounder that is necessary to consider. Objective In this study, we explored whether the mobile OS—Android and iOS—used during user assessments can be predicted by the dynamic daily-life TYT data. Methods TYT mainly applies the paradigms ecological momentary assessment (EMA) and mobile crowdsensing to collect dynamic EMA (EMA-D) daily-life data. The dynamic daily-life TYT data that were analyzed included eight questions as part of the EMA-D questionnaire. In this study, 518 TYT users were analyzed, who each completed at least 11 EMA-D questionnaires. Out of these, 221 were iOS users and 297 were Android users. The iOS users completed, in total, 14,708 EMA-D questionnaires; the number of EMA-D questionnaires completed by the Android users was randomly reduced to the same number to properly address the research question of the study. Machine learning methods—a feedforward neural network, a decision tree, a random forest classifier, and a support vector machine—were applied to address the research question. Results Machine learning was able to predict the mobile OS used with an accuracy up to 78.94% based on the provided EMA-D questionnaires on the assessment level. In this context, the daily measurements regarding how users concentrate on the actual activity were particularly suitable for the prediction of the mobile OS used. Conclusions In the work at hand, two particular aspects have been revealed. First, machine learning can contribute to EMA-D data in the medical context. Second, based on the EMA-D data of TYT, we found that the accuracy in predicting the mobile OS used has several implications. Particularly, in clinical studies using mobile devices, the OS should be assessed as a covariate, as it might be a confounder.