Objective: This study investigated the potential of estimating various mental workload levels during two different tasks using a commercial in-ear electroencephalography (EEG) system, the IDUN "Guardian". Approach: Participants performed versions of two classical workload tasks: an n-back task and a mental arithmetic task. Both in-ear and conventional EEG data were simultaneously collected during these tasks. In an effort to facilitate a more comprehensive comparison, the complexity of the tasks was intentionally increased beyond typical levels. Special emphasis was also placed on understanding the significance of gamma band activity in workload estimations. Therefore, each signal was analyzed across low frequency (1-35 Hz) and high frequency (1-100 Hz) ranges. Additionally, surrogate in-ear EEG measures, derived from the conventional EEG recordings, were extracted and examined. Main results: Workload estimation using in-ear EEG yielded statistically significant performance levels, surpassing chance levels with 44.1% for four classes and 68.4% for two classes in the n-back task and was better than a naive predictor for the mental arithmetic task. Conventional EEG exhibited significantly higher performance compared to in-ear EEG, achieving 80.3% and 92.9% accuracy for the respective tasks, along with lower error rates than the naive predictor. The developed surrogate measures achieved improved results, reaching accuracies of 57.5% and 85.5%, thus providing insights for enhancing future in-ear systems. Notably, most high frequency range signals outperformed their low frequency counterparts in terms of accuracy validating that high frequency gamma band features can improve workload estimation. Significance: The application of EEG-based Brain-Computer Interfaces (BCIs) beyond laboratory settings is often hindered by practical limitations. In-ear EEG systems offer a promising solution to this problem, potentially enabling everyday use. This study evaluates the performance of a commercial in-ear headset and provides guidelines for increased effectiveness.