A computerized system and method of teaching spelling interfaces with an application that captures a user's misspelled words and adds them to a word database. A teacher or instructor may also add words to the word database based on a user's curriculum, cross-curriculum or words of interest. The words in the word database are utilized to automatically create an individualized spelling teaching assignment and spelling Journal for a user. The user corrects any spelling mistakes that he or she has made and performs assignments with new words including hearing the words pronounced, spelling the words and writing sentences using the words. Spelling tests are also assigned. The teacher or instructor monitors the completion of the various assignments by the students and also monitors how well the assignments are performed.