This is a follow-up proposal to NPRP-09-873-1-129 “A natural language processing-based active and interactive platform for accessing English language content and advanced language learning” (completed August 2014) whose goal was to develop a English reading tutoring system called SmartReader. The SmartReader system provides active and interactive reading environment for English text making it possible for a student to interact with a text in a variety of ways using anytime-anywhere contextually guided access to information, such as word and phrase level operations, resolving anaphora, sentence simplification, name tracking, question generation and answering, summarization etc. In this follow-up project proposal, we would like to build up the expertise gained in this project and other work that we have been doing in deep question generation. In order to generate more sophisticated level of questions to see if the students do understand the texts not only syntactically but also semantically, we need to develop semantically motivated question generation from the multiple sources of sentences, using coreference resolution and detailed analysis of text, such as event semantics, inferences, paraphrases and semantic roles (e.g. agent, patient, time, location). The goal is to develop algorithm and technologies for analyzing short fragments of texts consisting of a sequence of sentences and generate questions whose answers require bring together information from multiple sentences using a nontrivial reasoning process. One very general and useful application area for this technology is to develop a tool that students can use to generate questions at their own pace and to practice exams for English comprehension test that is very similar to questions found in exams like TOEFL, SAT Verbal or ACT. We believe this could be deployed in Qatari high schools to improve the quality of learning English as a second language. The general techniques developed in this project can in the future be applied to a similar application working on Arabic texts.