AI-powered educational technologies have demonstrated measurable benefits for learners, but their design and evaluation have largely centered on K-12 contexts. As a result, many AI-supported learning systems remain poorly aligned with the needs, constraints, and goals of adult learners. To better understand how AI systems function in adult education, this paper examines the deployment of several AI learning technologies developed within a multidisciplinary, national research institute in the United States focused on adult learning and online education. Drawing on longitudinal deployment data, we conducted a reflexive thematic analysis to identify recurring challenges and design considerations across systems. These insights were synthesized into a set of 19 design guidelines intended to inform future AI-supported adult learning technologies. We demonstrate the utility of these guidelines through a heuristic evaluation of the deployed systems. Lastly, we present a guideline exploration tool that aids in the ideation of technologies by connecting the guidelines to stakeholder statements surfaced in the analysis process.

Existing AI agents typically execute multi-step tasks autonomously and only allow user confirmation at the end. During execution, users have little control, making the confirm-at-end approach brittle: a single error can cascade and force a complete restart. Confirming every step avoids such failures, but imposes tedious overhead. Balancing excessive interruptions against costly rollbacks remains an open challenge. We address this problem by modeling confirmation as a minimum time scheduling problem. We conducted a formative study with eight participants, which revealed a recurring Confirmation-Diagnosis-Correction-Redo (CDCR) pattern in how users monitor errors. Based on this pattern, we developed a decision-theoretic model to determine time-efficient confirmation point placement. We then evaluated our approach using a within-subjects study where 48 participants monitored AI agents and repaired their mistakes while executing tasks. Results show that 81 percent of participants preferred our intermediate confirmation approach over the confirm-at-end approach used by existing systems, and task completion time was reduced by 13.54 percent.

Intelligent tutoring systems (ITSs) have consistently been shown to improve the educational outcomes of students when used alone or combined with traditional instruction. However, building an ITS is a time-consuming process which requires specialized knowledge of existing tools. Extant authoring methods, including the Cognitive Tutor Authoring Tools' (CTAT) example-tracing method and SimStudent's Authoring by Tutoring, use programming-by-demonstration to allow authors to build ITSs more quickly than they could by hand programming with model-tracing. Yet these methods still suffer from long authoring times or difficulty creating complete models. In this study, we demonstrate that Simulated Learners built with the Apprentice Learner (AL) Framework can be combined with a novel interaction design that emphasizes model transparency, input flexibility, and problem solving control to enable authors to achieve greater model completeness in less time than existing authoring methods.