The Trump administration sent eight migrants held in Djibouti for weeks to South Sudan, where they fear they will face violence, following a flurry of court activity on Friday. A federal judge in Massachusetts denied an emergency request Friday evening from the migrants’ lawyers to block their deportation to the country,

The migrants were the subject of a lawsuit that halted their deportation to South Sudan and diverted them to a U.S. military base in Djibouti.

The fate of the migrants had become a flashpoint in the fight over the legality of the Trump administration’s campaign to deter immigration through high-profile deportations to so-called “third countries” where migrants say they face safety concerns,