Contextual factors in which learning occurs are crucial aspects that learning analytics and related disciplines aim to understand for optimizing learning and the environments in which learning occurs. In foreign vocabulary development, taking the notes or memos of learning contexts along with other factors, play an essential role in quick memorization and reflection. However, conventional tools fail to automate the learning contexts generation process as learners still need to take memos or e-notes to describe their vocabulary learning contexts. This paper presents the Image Understanding Project (hereafter IUEcosystem) that could produce smartly-generated learning contexts primarily in a learner's target languages. The IUEcosystem uses visual content analysis of lifelogging images as the sensor data to produce smartly-generated learning contexts that could be used as an alternative to handwritten memos or electronic notes. The IUEcosystem uses applied artificial intelligence to produce smartly-generated learning contexts. This intelligent learning environment collects a learner's learning satisfaction and interaction data and, later on, analyzes them to produce time-based notifications for enhancing retention. Furthermore, a new learning design is presented that aims to map a learner's prior vocabulary knowledge with new learning vocabularies to be learned. This learning design would help learners to review and recall prior knowledge while learning new vocabulary.