Context personalization, the practice of matching features of an instructional component to a learner’s interests and experiences, has been framed in the literature as a means by which to improve learning by enhancing motivation. However, a related perspective could consider personalization a form of instructional assistance, with the potential to support the learning of new concepts. In this paper, the assistance dilemma, known to be "a fundamental unsolved problem in cognitive science" (Koedinger, Pavlik, McLaren, & Aleven, 2008, p. 2159), is investigated for context personalization. Two research studies explore whether personalization can be considered a form of assistance, and how this intervention mediates performance measures.