In charge of the case is U.S. District Judge James Boasberg. Previous rulings on relevant topics have brought attention to his involvement in the case. He recently ruled against the Trump administration in a case concerning the deportation of Venezuelan migrants accused of joining the Tren de Aragua gang.

Former Attorney General Pam Bondi said Judge Boasberg “cannot be objective” in administration cases after that ruling. Bondi questioned Judge Boasberg’s “coincidental series of appointments” to high-profile Trump administration matters.

Despite those comments, Boasberg continues to rule over many administration-related litigation, including four recent instances. Federal court processes apparently assigned him randomly to each.

The Signal lawsuit hinges on whether federal officials must maintain encrypted app chats. American Oversight considers such statements official, especially when discussing military action or national security. The watchdog group wants accountability under the Federal Records Act, which requires executive branch record documentation and preservation.

Legal advances related to deportation policies have occurred in Boasberg’s courtroom. He tried to hold Trump administration officials in contempt last month for conducting El Salvador deportation flights in defiance of a court order. Boasberg’s proceedings were temporarily halted by the D.C. Circuit while it reviewed the government’s appeal.

The appeals court split 2-1. The administration won the temporary pause from Trump appointees Gregory Katsas and Neomi Rao. Obama-appointed Judge Cornelia Pillard dissented, believing that Boasberg’s contempt hearing was warranted.

The cases show continuous difficulties between judicial power and executive action, especially in immigration enforcement and foreign military policy, say legal scholars. In national security matters, the courts have typically deferred to the executive branch, but digital communication techniques have complicated record-keeping and accountability.

For now, the Signal case and accompanying court battles are uncertain. While the Supreme Court has interfered in some deportation cases, it has not yet addressed Signal communications or encrypted messaging in federal governance.

In the legal process, problems remain about the balance of power between organs of government, digital openness, and the changing concept of official communication in the digital age.