Education of any skill based subject, such as mathematics or language, involves a significant amount of repetition and pratice. According to the National Survey of Student Engagements, students spend on average 17 hours per week reviewing and practicing material previously learned in a classroom, with higher performing students showing a tendency to spend more time practicing. As such, learning software has emerged in the past several decades focusing on providing a wide range of examples, practice problems, and situations for users to exercise their skills. Notably, math students have benefited from software that procedurally generates a virtually infinite number of practice problems and their corresponding solutions. This allows for instantaneous feedback and automatic generation of tests and quizzes. Of course, this is only possible because software is capable of generating and verifying a virtually endless supply of sample problems across a wide range of topics within mathematics. While English learning software has progressed in a similar manner, it faces a series of hurdles distinctly different from those of mathematics. In particular, there is a wide range of exception cases present in English grammar. Some words have unique spellings for their plural forms, some words have identical spelling for plural forms, and some words are conjugated differently for only one particular tense or person-of-speech. These issues combined make the problem of generating grammatically correct sentences complicated. To compound to this problem, the grammar rules in English are vast, and often depend on the context in which they are used. Verb-tense agreement (e.g. "I eat" vs "he eats"), and conjugation of irregular verbs (e.g. swim -> swam) are common examples. This thesis presents an algorithm designed to randomly generate a virtually infinite number of practice problems for students of English as a second language. This approach differs from other generation approaches by generating based on a context set by educators, so that problems can be generated in the context of what students are currently learning. The algorithm is validated through a study in which over 35 000 sentences generated by the algorithm are verified by multiple grammar checking algorithms, and a subset of the sentences are validated against 3 education standards by a subject matter expert in the field. The study found that this approach has a significantly reduced grammar error ratio compared to other generation algorithms, and shows potential where context specification is concerned.