© 2019 Technology enhanced learning (TEL) represents an expert and intelligent paradigm in which technological affordances are used to facilitate learners' acquisition of domain knowledge (DK), where Ubiquitous–Learning (u–learning) is a TEL instance that recreates situated and immersive settings. However in such settings, learners are stressed by diverse, heterogeneous, and simultaneous stimuli that challenge their cognitive skills, increase the cognitive load, trigger emotional reactions, and bias conduct. Thus this research proposes a smart Sequencing approach that enables TEL systems to lead students to regulate their learning process. The essence of the proposal is a holistic self–regulated learning (SRL) model that encourage students to develop higher–order thinking through the practice of metacognitive skills, motivational factors, and behavioral affairs to become aware of their own learning endeavors. The approach was applied as part of the sequencing module of a u–Learning system, where students follow its suggested cognitive strategies to assist them during the programming of control equipment. Results show that, although experimental subjects had to deal with higher cognitive load, they are expected to reach higher learning achievements than their control peers. The experience reveals how TEL systems are enabled to foster learners to handle their own apprenticeship processes. As a consequence, the smart sequencing functionality of TEL is cognitively enhanced to facilitate students the simultaneal acquisition DK and development of higher–order thinking.