While the term task load (TL) refers to external task demands, the amount of work, or the number of tasks to be performed, mental workload (MWL) refers to the individual’s effort, mental capacity, or cognitive resources utilized while performing a task. MWL in multitasking scenarios is often closely linked with the quantity of tasks a person is handling within a given timeframe. In this study, we challenge this hypothesis from the perspective of electroencephalography (EEG) using a deep learning approach. We conducted an EEG experiment with 50 participants performing NASA Multi-Attribute Task Battery II (MATB-II) under 4 different task load levels. We designed a convolutional neural network (CNN) to help with two distinct classification tasks. In one setting, the CNN was used to classify EEG segments based on their task load level. In another setting, the same CNN architecture was trained again to detect the presence of individual MATB-II subtasks. Results show that, while the model successfully learns to detect whether a particular subtask is active in a given segment (i.e., to differentiate between different subtasks-related EEG patterns), it struggles to differentiate between the two highest levels of task load (i.e., to distinguish MWL-related EEG patterns). We speculate that the challenge comes from two factors: first, the experiment was designed in a way that these two highest levels differed only in the quantity of work within a given timeframe; and second, the participants’ effective adaptation to increased task demands, as evidenced by low error rates. Consequently, this indicates that under such conditions in multitasking, EEG may not reflect distinct enough patterns to differentiate higher levels of task load.