Bail reform is happening. Across the country, jurisdictions are beginning to recognize that contemporary pretrial systems rooted in money bail are discriminatory, ineffective, and (by and large) unconstitutional. A common and substantial component of contemporary reforms is an increased reliance on conditional release as an alternative to pretrial incarceration. In many ways, conditional release represents an improvement over money bail, but the practice of conditional release has its own pitfalls. This Article identifies unforeseen and unplanned harms that can result from a system of conditional release and proposes five principles that jurisdictions can follow to eliminate or mitigate these harms. As the options for pretrial conditions continue to expand, judges may impose more conditions than are necessary, including conditions that are burdensome and ineffective. Because pretrial monitoring is inexpensive—especially when subsidized by user fees for pretrial monitoring—there is a risk that courts will impose monitoring and other conditions on people who would previously have been released without conditions. Taken together, these harms can prolong people’s involvement in the criminal justice system, restrict their liberty in profound ways, set them up for pretrial incarceration through technical violations, and saddle them with unaffordable debts. To responsibly use conditional release without replicating the harms of money bail, jurisdictions should adopt the following five principles. One, release on recognizance should be the norm and conditional release the exception. Two, the principle of parsimony should guide decisions over what conditions of release to impose—meaning that burdens placed on defendants and restrictions of their liberty should not exceed the legitimate interests of the government. Three, conditions should be minimal, related to the charged conduct, and proportionate to the risk of flight and pretrial criminal activity. Four, jurisdictions should not charge fees for conditional release, pretrial services, or pretrial monitoring. Five, restrictions on pretrial liberty should be evidence-based.