In a technology driven world, efforts are being made to make education/learning available to individuals at any time with no compromise in the quality of teaching/training. To make learning flexible, different techniques such as distributing learning material, uploading audio lectures on the web, and creating intelligent tutoring systems (ITS) are being used. The technique considered here is an adaptive ITS, a system that replicates the learning that occurs in a student teacher relationship. This thesis develops an adaptive intelligent tutoring system architecture prototype where the addition, modification and removal of educational material are relatively easy. The resulting software will take into account: the goals of the specific educational experience, the concepts to be covered, the preferred learning style of the student, measures to detect misuse of the system functionality, behavior based on the student's performance and the generation of hint sequences and feedback messages to improve learning gain. The system will accomplish these objectives by assessing the student's prior knowledge level, observing the actions performed by the student and by adapting to his/her learning abilities. The ITS will attempt to be more intelligent by performing some actions traditionally done by a human teacher - such as diagnosing misconceptions, identifying the most suitable learning style, stressing concepts that the student is finding difficult to understand, switching back to the learning material if the student shows no improvement after a set of trials. The system makes sure that the student is getting feedback where appropriate. Using this prototype system, the student will be tutored to acquire declarative knowledge. A problem based learning (PBL) approach will be used to strengthen the acquired knowledge by providing a high degree of personal attention to the student. To show how the prototype system works, an example of analysis of a control system problem using bode plot technique will be used to assist the student in using the technique to perform the stability analysis of an analog, linear, time-invariant control system problems and to recommend a controller to attain stability (if the system is not stable). Ideas of porting the system from standalone to web-based architecture and features required for collaborative learning will be discussed and an architecture for a web-based tutoring system for supporting multiple students enabling communication between students and sharing data among them will be proposed. / Electrical and Computer Engineering