This article examines the U.S. Supreme Court's rulings in Padilla v. Kentucky and Turner v. Rogers to show the civil consequences for recently released offenders that result from their criminal convictions. In the case of Padilla v. Kentucky, courts considered whether civil consequences resulting from criminal convictions were either direct or indirect results of the convictions, whereas Turner v. Rogers was the opposite case, criminal consequences resulting from the outcome of civil proceedings. The article discusses both the broad and specific application of the Court's rulings in each of the two cases. Following this discussion, the article presents a new framework, the significant entanglement framework, on whether the imposition of a civil consequence of a criminal conviction gives rise to sixth amendment protections. The new framework has three main points: 1) the direct-collateral distinction is no longer applicable or useful in these cases; 2) a key consideration in whether the sixth amendment should apply in these cases is the significance of the consequence to the defendant; and 3) the degree of entanglement between civil consequences and criminal law will determine whether sixth amendment protections apply in these types of cases. The final section of the article presents examples of the application of the significant entanglement framework as it relates to deprivation of liberty, financial loss, and right to counsel, among others.