Federal agents took three people into custody at immigration courts in New York City over the last week in what lawyers said appears to be the first grave violations of two orders by federal judges barring such arrests.

On Thursday, U.S. Immigration and Customs Enforcement agents arrested an Ecuadorian man at a court at 26 Federal Plaza and a man from the Dominican Republic at another court at 290 Broadway, both in Lower Manhattan. The arrests continued on Monday, when ICE agents detained a third man, originally from Guatemala, at 290 Broadway.

In legal filings challenging the detentions of the men taken Thursday, advocates with the nonprofit Make the Road New York accused ICE of not only violating their clients’ right to due process, but also of brazenly flouting a federal court order.

The judge’s order barred ICE from making arrests at Manhattan immigration courts in all but a narrow handful of exceptions, while a similar ruling issued on June 23 from a federal court in California applies nationwide.

By detaining the men at court on Thursday, ICE appears to be directly contravening the New York order without yet providing a justification, according to Rep. Dan Goldman, D-N.Y.