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Persons deprived of their liberties as a result of administrative detention for immigration reasons face a multitude of serious challenges. There is currently no recognized right to the government-appointed representation in immigration proceedings. As a result, on a very small percentage of immigrants obtain pro bono or any other kind of legal representation. This problem is compounded by the fact that most immigration detainees are detained in remote rural areas where the private bar is virtually unavailable. Those who are fortunate to obtain pro bono or other types of legal representation also face some serious challenges at the different stages of the deportation or removal proceedings. This article discusses the challenges of representing detained non-citizens in deportation proceedings from the prism of the Penn State Dickinson School of Law's Immigration Clinic ("DSL Immigration Clinic"). The discussion is presented in a continuum. Most of the immigration detainees are placed in deportation proceedings after serving a state or federal criminal sentence. What transpires in the criminal proceedings often carries serious immigration consequences. As such, the continuum must necessarily begin with a discussion of the challenges faced in deportation proceedings. These challenges are discussed under the title "Pretrial Challenges" in Part II. Part III deals with the challenges associated with the merits hearing in the removal proceedings, including procedural and evidentiary issues. Part IV outlines post trial challenges, including prolonged detention and the complexities of obtaining judicial review. Part V provides a brief conclusion.