Nonprofit legal services provider Las Americas Immigrant Advocacy Center lost a bid on Friday to halt the Texas attorney general's investigation of the organization's activities, with a federal judge saying the group waited too long to file its complaint.

U.S. District Judge David Guaderrama dinged the organization for waiting until after the courthouse closed on Sept. 25 to file its complaint, leaving the court just one full business day to rule on its request for a temporary restraining order before the Friday deadline for the group to turn over documents to Attorney General Ken Paxton's office.

"Plaintiff hasn't identified any exigent circumstances that prevented it from moving for a TRO any sooner," Judge Guaderrama said.

Las Americas has accused Paxton of harassing and intimidating numerous immigrant service organizations, saying it believes it is the first immigration legal services nonprofit to receive a civil investigative demand, or CID, under the Texas Deceptive Trade Practices Act. 

That CID was related to an investigation into "fraudulent and deceptive legal representations and services," as governed by the act.

According to Judge Guaderrama's opinion, Las Americas was aware of the investigation and the Friday deadline on Sept. 4, when the attorney general's office served the nonprofit with a civil investigative demand.

"As of that date, plaintiff knew everything that it needed to know before it could file this lawsuit and move for a TRO," the judge said.

Judge Guaderrama rejected Las Americas' contention that meeting the Sept. 27 deadline would pose a burden to the organization because of its "small team and limited resources," saying the group failed to identify how that would have prevented it from filing the suit sooner.

Such late requests for a temporary restraining order, on "the eve of the adverse occurrence that they're asking the court to prevent," are disfavored because they deprive defendants of the opportunity to meaningfully respond, Judge Guaderrama said.

Las Americas was given until Sept. 27 to provide documents related to immigrants and beneficiaries applying for a Biden administration program for vetted citizens of Cuba, Haiti, Nicaragua and Venezuela, which grants them temporary admission to the U.S. and work authorization.

Las Americas contends the CID "unconstitutionally interferes with" its right to expressive association by requiring the group to turn over all communications it sent to the U.S. Department of Homeland Security or U.S. Citizenship and Immigration Services, including confidential client documents containing their identities and information about their immigration status.

Las Americas accused Paxton of "weaponiz[ing] unprecedented legal strategies against immigrant rights organizations" by petitioning for the dissolution of their corporate charters, bringing actions for prelawsuit discovery and demanding records and sworn statements under the Texas Business Organizations Code.

These allegations come after, as Las Americas noted in its complaint, Texas Gov. Greg Abbott asked the Texas Office of the Attorney General in a December 2022 letter to investigate the potential role of nongovernment organizations in "planning and facilitating the illegal transportation of illegal immigrants across our borders."

Counsel for Las Americas and the Texas Office of the Attorney General did not immediately respond to requests for comment.

Las Americas is represented by Thomas M. Melsheimer, Scott C. Thomas, Michael A. Bittner and Ashley J. Wright of Winston & Strawn LLP, and Aron Thorn, Daniel Hatoum, Kassandra Gonzalez and Travis Walker Fife of the Texas Civil Rights Project.

Paxton is represented by Edward L. Marshall of the Texas Attorney General's Office.

The case is Las Americas Immigrant Advocacy Center v. Ken Paxton, case number 3:24-cv-00352, in the U.S. District Court for the Western District of Texas.

--Additional reporting by Andrea Keckley. Editing by Linda Voorhis. 

Update: This article has been updated to add details from the case.