With the high rate of guilty pleas in our justice system, attention needs to be paid to the consequences of these convictions, beyond the sanctions imposed at a sentencing hearing. Namely, the increase in guilty pleas has led to an unprecedented number of United States citizens with restrictions imposed on them that limit their employment, access to housing or government assistance, and to an unprecedented number being deprived of the right to vote. These collateral consequences of convictions, and the disenfranchisement resulting from the loss of the vote, can disrupt an individual’s life often to a greater extent than the short imprisonment many convicted felons face. This chapter looks at the effects of collateral consequences and disenfranchisement, how these may play into the decision to accept a plea (and who should be informing defendants about these restrictions), and whether proper consideration of the effect of collateral consequences is possible given how our current system of pleas is structured. Areas for future research are also identified.