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Upsolve, Inc., et al. v. Letitia James, Attorney General of New York

Paid petition · United States Court of Appeals for the Second Circuit, No. 22-1345 · judgment September 9, 2025


Certiorari denied · March 30, 2026
Pre-decision estimate: 5% cert probability

Before the decision, roughly the 4.1% base rate. The model weighted this up for counsel who has won certiorari before, a Second Circuit decision below, and a business petitioner, and down for a state or local-government respondent.

Question presented

Petitioners, a nonprofit corporation and one of its volunteers, wanted to train nonlawyers to offer narrow, specific advice to poor people facing specific legal problems—a program that turned out to be prohibited by New York’s prohibition on the “unauthorized practice of law,” which reaches even unpaid spoken advice about the law. In the case below, the Second Circuit held that this restriction on Petitioners’ speech is content-neutral because it is not aimed at the content of their speech (which is communicating legal advice and opinions to particular clients) but is instead aimed at the “purpose, focus, and circumstance” of their speech, which is “the rendering of legal advice and opinions to particular clients.” The question presented is: Is a law whose application is triggered by communicating about a particular topic nonetheless content-neutral so long as the law can be described as aimed at the “purpose, focus, and circumstance” of the speech rather than at its content?

Counsel of record

For petitioner
Robert James McNamara
Institute for Justice

For respondent
Barbara Dale Underwood
New York Solicitor General

Case

Conference history
Distributed for 1 conference

Amicus briefs
4 cert-stage

Linked docket
25A381

Proceedings

  1. Mar 30 2026
    Petition DENIED.
  2. Mar 12 2026
    Brief amici curiae of Pacific Legal Foundation, et al. filed. (Distributed)
  3. Mar 12 2026
    Brief amicus curiae of Cato Institute filed. (Distributed)
  4. Mar 12 2026
    Brief amici curiae of Professor Rebecca L. Sandefur, et al. filed. (Distributed)
  5. Mar 12 2026
    Brief amicus curiae of Manhattan Institute filed. (Distributed)
  6. Mar 11 2026
    DISTRIBUTED for Conference of 3/27/2026.
  7. Mar 11 2026
    Supplemental brief of petitioners Upsolve, Inc., et al. filed. (Distributed)
  8. Mar 05 2026
    Waiver of right of respondent Letitia James to respond filed.
  9. Feb 06 2026
    Petition for a writ of certiorari filed. (Response due March 12, 2026)
  10. Dec 17 2025
    Application (25A381) granted by Justice Sotomayor extending the time to file until February 6, 2026.
  11. Dec 10 2025
    Application (25A381) to extend further the time from January 7, 2026 to February 6, 2026, submitted to Justice Sotomayor.
  12. Oct 05 2025
    Application (25A381) granted by Justice Sotomayor extending the time to file until January 7, 2026.
  13. Sep 29 2025
    Application (25A381) to extend the time to file a petition for a writ of certiorari from December 8, 2025 to January 7, 2026, submitted to Justice Sotomayor.