United States Court of Appeals For the Seventh Circuit ____________________ No. 22-3140 UNITED STATES OF AMERICA, Plaintiff-Appellee, v. THOMAS OSADZINSKI, Defendant-Appellant. ____________________

Appeal from the United States District Court for the Northern District of Illinois, Eastern Division. No. 1:19-cr-00869-1 — Robert W. Gettleman, Judge. ____________________

ARGUED JANUARY 8, 2024 — DECIDED MARCH 28, 2024 ____________________

Before WOOD, SCUDDER, and ST. EVE, Circuit Judges. SCUDDER, Circuit Judge. Thomas Osadzinski appeals his conviction for providing material support to a terrorist organ- ization. In 2019 he created a computer program that allowed ISIS (the Islamic State in Iraq and Syria) and its followers to rapidly duplicate terrorist propaganda videos online and thereby to stay a step ahead of efforts by the United States and other western governments to thwart the organization’s me- dia campaign. Osadzinski shared his computer program with 2 No. 22-3140 people he believed were ISIS supporters, taught them how to use it, and deployed it to compile and disseminate a large trove of ISIS media. Osadzinski claims that his conviction violated the First Amendment because his actions constituted independent free expression. Alternatively, he contends that he lacked fair notice that his offense conduct violated the material-support statute, 18 U.S.C. § 2339B. He further argues that the evidence the government presented at his trial was insufficient to sup- port his conviction. We disagree on all fronts. Applying the guidance the Supreme Court supplied in Holder v. Humanitarian Law Project, 561 U.S. 1 (2010), we conclude that, to the extent that Osadzinski engaged in expressive activity, the activity was coordinated with or directed by ISIS, a known terrorist organization. That leads us to affirm. I A In February 2018 the Federal Bureau of Investigation re- ceived a tip about Thomas Osadzinski, an undergraduate stu- dent studying computer science in Chicago, Illinois. The tip- ster reported that Osadzinski had become obsessed with ISIS propaganda and was in regular online communication with extremists. The tip proved accurate. On June 6, 2018, an anonymous user—later identified as Osadzinski—posted a screenshot of instructions for manufacturing a homemade explosive device in a pro-ISIS online forum called “weapons.” The screenshot described the instructions as “a gift to the mujahideen who operate in [infidel] lands” so that they “might strike a blow behind the enemy lines, like we did in Paris”—a reference to No. 22-3140 3 ISIS bombings and shootings in France in November 2015 that killed 130 people and injured hundreds more. An undercover FBI operative—whom we refer to as Agent 1—saw Osadzinski’s post and initiated a conversation. Posing as a fellow ISIS supporter in the Middle East, Agent 1 offered to connect Osadzinski to members of the Islamic State. Osadzinski replied, “If you trust the brothers sure send [] them my way.” Osadzinski shared that he was attending “a top school for computers” and “can help many brothers.” Later he reiterated the same point in more direct terms: “If any brothers need help with security tell them to come to me.” Three weeks passed. At the end of June 2018, Agent 1 checked back in. Osadzinski reacted by apologizing, saying he had to “stay passive for now” and could not contact ISIS members because he believed the FBI was surveilling him. But he reaffirmed his commitment to the broader ISIS cause, pledging that “if i must i will attain shahadah [ma