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For nearly 30 years, people arrested by immigration enforcement officials inside the United States could typically live freely as they waited for the results of their immigration cases. Under the Trump administration, officials have tried to keep them locked up as part of its major deportation campaign. The legality of that approach is now hotly contested in federal courts.

A Boston-based federal appeals court heard oral arguments in one such case Monday. The case could reverberate across New England 鈥� and is looking increasingly likely to wind up before the Supreme Court.

The class action lawsuit, Guerrero Orellana v. Moniz et al., deals with whether unauthorized immigrants detained by federal officials in the U.S. interior are entitled to a bond hearing before an immigration judge under federal law. Such hearings determine whether an immigrant can live in the U.S. freely while they fight their deportation, or if they must be jailed until litigation ends.

The Trump administration argues that the Immigration and Nationality Act (INA), the nation鈥檚 primary immigration statute, requires that any unauthorized immigrant detained on U.S. soil must be held without bond. Jose Arnulfo Guerrero Orellana, an immigrant from El Salvador who entered the country unlawfully in 2013, argues that the government鈥檚 position runs contrary to its own long-standing practice and the plain text of the law.

Since Congress reformed the INA in 1996, both Republican and Democratic administrations have treated virtually all immigrants detained within the U.S. as eligible for a bond hearing. But last July, the Department of Homeland Security issued a memo , arguing instead that unauthorized immigrants were subject to mandatory detention. The Board of Immigration Appeals, an appellate immigration court that鈥檚 part of the executive branch, that rule in September.

Immigration detentions have surged as the Trump administration pushes its mass deportation agenda. In January 2025, the government held roughly 40,000 people in immigration detention. A year later, 68,000 people 鈥� a 70% increase, according to an analysis of government data by the American Immigration Council. The number of people held in immigration detention for more than a year increased from 938 at the end of October 2025 to 2,084 by the end of March 2026, public reports from U.S. Immigration and Customs Enforcement show.

The arguments dividing courts

Other cases like Monday鈥檚 have also reached the nation鈥檚 second-highest courts, with mixed outcomes. and courts sided with the Trump administration earlier this spring. Last week, the New York-based 2nd Circuit court , setting up a split and raising the possibility of Supreme Court review.

Monday鈥檚 oral argument in Boston hinged on several in-the-weeds questions about how to interpret the language of Sections 1225 and 1226 of Title 8 of the U.S. Code, which contains immigration law. Traditionally, Section 1225 has dealt with inspection, admission, and detention at ports of entry, while Section 1226 has governed the detention of immigrants already residing in the country, lawfully or not.

The sides disagree on whether an 鈥渁pplicant for admission,鈥� which is as 鈥渁n alien present in the United States who has not been admitted or who arrives in the United States,鈥� is the same thing as someone 鈥渟eeking admission.鈥� Under Section 1225, an immigrant 鈥渟eeking admission鈥� who is 鈥渘ot clearly and beyond a doubt entitled to be admitted鈥� should be detained while awaiting proceedings.

The government argues that the phrases are synonymous. 鈥淚 don鈥檛 think that 鈥榮eeking admission鈥� was supposed to essentially swallow the definition for applicant for admission,鈥� said John Bailey, a lawyer for the Justice Department. 鈥淪omeone who is an applicant for admission is seeking admission.鈥�

Lawyers for Mr. Guerrero Orellana, by contrast, argue that the two terms are distinct. 鈥淲hat the government has done is import into 鈥榮eeking admission鈥� this second term,鈥� said Adriana Lafaille, a lawyer for the American Civil Liberties Union. 鈥淭hese terms are doing different things.鈥�

Because Mr. Guerrero Orellana was arrested at a traffic stop in Massachusetts, and was not presenting himself to an immigration official at the border or a port of entry at that time, his lawyers argue that he was not seeking admission.

In other similar cases over bond hearings, hundreds of appointed by both Republicans and Democrats, have by and large agreed with the latter interpretation of the law鈥檚 language. A District Court judge in Massachusetts ruled against the Trump administration setting up the current legal clash.

The panel of three judges on Monday asked pointed questions of both sides. Judges Sandra Lynch and Lara Montecalvo repeatedly asked the government to clarify its position on why the statute says 鈥渟eeking admission.鈥�

鈥溾�楽eeking admission鈥� seems to require some act on the part of an applicant for admission,鈥� Judge Lynch said. 鈥淚f [Congress] wanted mandatory detention of every applicant for admission, it would be very easy just not to use the phrase at all.鈥�

Judge Joshua Dunlap asked Ms. Lafaille several times if the ACLU鈥檚 reading of the law would make parts of the INA superfluous, which judges try to avoid in their rulings. He implied that both parties argue that a statute can use two words to mean one thing.

鈥淭hat same argument is what I understand both of you to be making,鈥� he said. 鈥淵ou can use similar terms 鈥� not the exact same terms 鈥� in the same statute.鈥�

U.S. Immigration and Customs Enforcement has already arrested in Massachusetts alone since Mr. Trump鈥檚 election, WBUR reported, almost five times the number arrested in the last 415 days of the Biden administration. The 1st Circuit鈥檚 decisions cover Maine, Massachusetts, New Hampshire, Rhode Island, and Puerto Rico.

Editor鈥檚 note: This story was updated on the same day of publication to note the portion of the U.S. Code where Sections 1225 and 1226 are located.