Automatic generation of math word problems (MWPs) is a challenging task in Natural Language Processing (NLP), particularly connecting it to real-life problems because it can benefit students in developing a higher level of mathematical thinking. However, most of the MWPs are presented within a scholastic setting in a decontextualized way. This paper describes a prototype system that generates authentic math word problems (i.e., real-life problems) using authentic contextual recognition with controlled difficulty levels. Our innovative approach includes the acquisition of authentic contextual information through recognition technology, an instructional-based prompt generator for three different difficulty levels, and question generation through the Generative Pre-trained Transformer (GPT) model. We evaluated the performance of the system in terms of the quality of generated questions using automatic evaluation and human evaluation. Further, we assessed the usability of the system using heuristic evaluation. The automatic evaluation showed our generated MWPs were relevant for geometry topics and varied in sentence generation. The human evaluation found our system generated more realistic problems with satisfactory language quality and mathematical validity. Our system also produced more questions with higher difficulty levels based on human evaluation. Heuristic evaluation captured the usability of the system and highlighted the potential to be applied in a pedagogical context for mathematics learning.