There is now a preponderance of evidence suggesting that the types of online course management software (OCMS) used in purely online undergraduate college courses, do not meet the needs of younger immature students. These students often lack the learning skills necessary to succeed in such courses, nor do the popular OCMS include the vigilance mechanisms to guide such students to successful course completion in the absence of face-to-face human instruction. This paper explores the literature relevant to design theory, learning theory, decision support, and vigilance, to develop a design theory as a guide to software developers and academics studying how to design future systems for the immature student in accordance with the latest research.