Update, Dec. 10, 2025:
The U.S. District Court for the Eastern District of Kentucky directed Immigration and Customs Enforcement to release Dailin Pacheco-Acosta from custody on Wednesday, less than a day after an immigration court judge in Chicago granted asylum to Pacheco-Acosta and her husband, Diego Ugarte-Arenas.
Pacheco-Acosta did not immediately leave Campbell County Detention Center in Kentucky, which contracts with ICE to hold detainees facing immigration charges. The couple’s attorney, Ben Crouse, told Wisconsin Watch he filed a new bond motion for Pacheco-Acosta on Wednesday afternoon, and she will return to Madison once the immigration court approves her bond.
But her husband will remain in custody in the Dodge County Jail while awaiting the U.S. Department of Homeland Security’s potential appeal of the couple’s asylum claim.
If DHS appeals and Ugarte-Arenas remains in custody, their next legal phase could take another 6 months. But Crouse noted another lawsuit winding through federal courts could reopen the more straightforward path for immigrants in ICE custody to be released on bond. That case sits in the 7th Circuit U.S. Court of Appeals, whose jurisdiction includes Wisconsin.
If ICE releases Ugarte-Arenas from the Dodge County Jail, the couple’s case would shift to the immigration court system’s “non-detained docket,” Crouse said, where cases move far slower than those of immigrants in custody.
Original story, Dec. 9, 2025:
A Chicago immigration court judge has granted the asylum request of a Madison couple who U.S. Immigration and Customs Enforcement (ICE) officers arrested during a routine check-in at the agency’s Milwaukee office in October.
Judge Eva Saltzman sided with Dailin Pacheco-Acosta and Diego Ugarte-Arenas on Tuesday afternoon, but the Department of Homeland Security (DHS) – ICE’s parent agency – reserved the right to appeal.
The ruling does not automatically free the couple from ICE custody.
“It’s not over,” said Ben Crouse, the couple’s Milwaukee-based attorney.
Ugarte-Arenas remains in the Dodge County jail, which contracts with ICE to hold immigrants facing deportation, and Pacheco-Acosta sits in a county jail in northern Kentucky. A recent Trump administration policy has prevented them from posting bond and continuing their asylum case from Madison, where they settled in 2021 after fleeing Venezuela.
The couple crossed the U.S.-Mexico border without a visa, but because of a clerical error by Customs and Border Patrol officers they encountered near Eagle Pass, Texas, they did not initially land before an immigration court and were instead able to file for asylum with U.S. Citizenship and Immigration Services upon reaching Wisconsin. The couple refiled for asylum with the immigration court in Chicago after their arrests in October. Neither has a past criminal conviction nor a pending criminal charge.
As they await the next step in their legal battle, the Trump administration is defending the policy that has kept the couple in custody for more than a month, even after a federal judge in California challenged its legality. How higher courts rule will determine whether thousands of immigrants in ICE custody can post bond for the first time in months.
Trump officials seek ‘mandatory detention’
Reversing decades of precedent, DHS announced in July that most immigrants in ICE custody would be ineligible for bond and are instead subject to “mandatory detention.” The Board of Immigration Appeals, a body within the U.S. Department of Justice (DOJ) that sets rules for immigration courts, sided with DHS in September.
But a Nov. 20 ruling by U.S. Judge Sunshine Sykes of the Central District of California gave the Madison couple and ICE detainees nationwide a moment of optimism.
Sykes partially ruled on the side of four undocumented immigrants ICE picked up during a June immigration raid in Los Angeles. The four immigrants, represented by attorneys from multiple immigrant rights organizations, had filed a class action lawsuit challenging the rule after they were denied bond.
But both DHS and DOJ, which oversees immigration court judges, argue Sykes’ decision doesn’t apply to all immigrants in similar positions nationwide. Many immigration court judges, including in Chicago, the court with jurisdiction over most immigrants detained in Wisconsin, have continued to deny bond hearings for immigrants in custody, citing the administration’s reasoning.
DOJ spokesperson Kathryn Mattingly said department leaders are not instructing immigration judges to specifically reject bond motions.
“Immigration judges are independent adjudicators and decide all matters before them on a case-by-case basis,” Mattingly wrote in a statement to Wisconsin Watch.
Next steps for Madison couple
Crouse, the couple’s attorney, filed motions seeking the Madison couple’s bond before the California ruling. Their motions, even if futile, could help clarify the scope of Sykes’ ruling, he said.
Crouse and other attorneys are separately testing the last remaining pathway to release: filing “habeas petitions” asking judges to rule on the lawfulness of their clients’ detention. A district court judge in Milwaukee denied a petition for Ugarte-Arenas on Monday, and Pacheco-Acosta is still awaiting a decision from a judge in Kentucky. If Pacheco-Acosta’s petition is successful, she will receive a bond hearing.
Back in Chicago, Judge Saltzman is preparing a written order outlining her reasoning for granting the couple asylum. DHS signaled plans to challenge her decision before the Board of Immigration appeals. It has 30 days to do so after Saltzman releases her written order.
Though Crouse called the couple’s case strong — not least because of mounting U.S. military actions in Venezuela — he noted that recent board decisions siding with DHS mean nothing is assured.
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