The increasing dominance of English has elevated the need to develop an ability to effectively communicate in writing, and this has put a strain on second language education programs worldwide. Faced with time-consuming and copious commenting on student drafts and inspired by the promise of computerized writing assessment, many "educational technology enthusiasts are looking to A WE [automated writing evaluation] as a silver bullet for language and literacy development" (Warschauer & Ware, 2006, p. 175). This chapter reviews what AWE offers for learners and teachers and raises a number of controversies regarding A WE effectiveness with the underlying message that clear milestone targets need to be set with respect to A WE development, implementation, and evaluation in order to ensure positive impact of this technology on L2 writing. In support of this message, the chapter introduces an example-lADE, a prototype of contextbased A WE conceptualized and operationalized to address latent issues through a synthesis of theoretical premises and learning needs. Multifaceted empirical evaluation of lADE further provides insights into processes triggered by interaction with A WE technology and foregrounds a call for future research needed to inform effective application of AWE in L2 writing classrooms.