United States v. Thomas Osadzinski

In the

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 [martyrdom].”

These communications caused the FBI to enhance their

surveillance of Osadzinski. In February 2019 the Bureau sent

a second undercover agent to visit his classroom and pretend

to be a representative from a software company. Agent 2 se-

lected Osadzinski to test a new antivirus program in exchange

for $1,000. After several meetings, he confided in Osadzinski

that he too supported ISIS, and the two developed a friend-

ship of sorts.

That same month Osadzinski contacted a third agent who

he believed to represent another ISIS-aligned online group.

Osadzinski shared several of his projects with Agent 3,

including an article he had written for a pro-ISIS youth mag-

azine, two ISIS propaganda videos to which he had

4 No. 22-3140

contributed English subtitles, and a third ISIS video that he

had narrated. Agent 3 asked Osadzinski whether he was

doing this to support the Islamic State or for jihad. “[B]oth,”

Osadzinski responded.

In March 2019 Agent 3 sent Osadzinski a report indicating

the number of social media accounts that had been removed

from online platforms due to terrorism-related content. The

two denounced western governments’ efforts to suppress and

censor ISIS’s message. Osadzinski then asked Agent 3 if he

had seen a video called Inside 8.

Inside 8 is an ISIS propaganda video that calls on support-

ers to help maintain and magnify the group’s presence online.

The video depicts ISIS operatives hunched over computer

screens writing code while images of explosions flash and a

nasheed rings out in the background. All the while, a narrator

laments that the United States has “beguiled the people for so

many years by monopolizing the media and using it to spread

its false notion of invincibility.” The narrator urges viewers to

“support your khilafah on the digital front” by “amplif[ying]”

ISIS’s call, “adopt[ing] the messaging put out by its official

media,” and “striv[ing] to disseminate it far and wide.” The

film then proclaims a call to action:

[S]trive patiently in the digital arena, and do not

allow the disbelievers to enjoy a moment of

sleep or to live a pleasant life. If they close one

account, open another three. And if they close

three, open another 30. … For with every press

of a key on the keyboard, you amplify the force

and reach of the explosives. And with every

click of a mouse and every piece of content you

No. 22-3140 5

disseminate, … your support enrages the disbe-

lievers.

Echoing Inside 8’s primary message, Osadzinski told

Agent 3: “[If] they delete 1[,] we make 2 more.” He then

informed Agent 3 that he had learned a computer technique

that would enable the rapid duplication of ISIS media files on

the social media platform Telegram.

In April 2019 Agent 3 introduced Osadzinski to a fourth

undercover colleague who claimed to be a radical ISIS sup-

porter in need of translation assistance to conduct a bomb at-

tack. While Osadzinski did not ultimately provide that trans-

lation, he did tell Agent 4 that he was working on several

computer projects to help fellow supporters avoid surveil-

lance. “I love learning about computers” he expressed,

“theyre very useful for jihad.”

In August 2019 Agent 3 asked Osadzinski about his

progress. Osadzinski replied by sending screenshots of his

computer code, along with both a pro-ISIS Telegram channel

that his code was duplicating in real time and a large offline

database of ISIS media files. Osadzinski explained that he had

created a custom software program that automatically copied,

organized, and distributed ISIS videos housed on Telegram.

He then emphasized that this was only “one small section” of

what he was working on and that he intended to expand his

archive—which already contained 3,762 items—to include all

content released by ISIS. Osadzinski told Agent 3 that his ul-

timate objective was to “spread it everywhere.”

To disseminate his collection of ISIS media without detec-

tion, Osadzinski planned to convert his offline archive into a

torrent file—which can be simultaneously downloaded from

6 No. 22-3140

multiple servers at once to boost transmission speeds and ob-

scure file origins. He told Agent 3 that he then intended to

publicly broadcast the link, effectively creating a permanent

archive that “nobody can take … down.” Western intelligence

agencies, Osadzinski boasted, would only be able to “watch”

as “the media jihad will never end.”

By the summer of 2019 Osadzinski had set to work execut-

ing his plan. In August he instructed Agent 3 to share his

Telegram channel “with anyone you trust.” He also sent the

channel to Agent 2, instructing him to do the same. In October

2019 Osadzinski reached out to a fifth undercover operative,

believing him to be a representative of an organization that

translated official ISIS publications into English. Introducing

himself as a “munasir” (ISIS supporter) who “copies chan-

nels,” Osadzinski shared a screenshot of a Telegram channel

he had created using his code with over 17,000 ISIS media

files.

Meanwhile, Osadzinski taught his computer program to

other ISIS supporters. For several hours over multiple days,

he instructed Agent 5 on the details of how to run his com-

puter script. He did the same for Agent 2. During an in-

person meeting on October 10, 2019, Agent 2 asked

Osadzinski if he could “walk me through [the program] step

by step” so Agent 2 could “take a screenshot” and “translate

it for the brothers in dawla [ISIS].” “I’ll show you how,”

Osadzinski agreed. He then provided detailed instructions

showing Agent 2 how to run the code, download its accom-

panying software, and troubleshoot the program.

Osadzinski still was not done. To expand access to his

program to an even broader audience of ISIS supporters, he

wrote an instructional document called Heralds of the

No. 22-3140 7

Internet. Heralds consisted of step-by-step directions on how

to organize online ISIS content using Osadzinski’s program,

with each step accompanied by screenshots of the necessary

source code. Osadzinski shared the document with Agent 3

in August 2019. He also told Agent 3 that he planned to write

another instruction manual teaching “brothers” how to copy

channels on Android devices.

Osadzinski never got the chance. On November 18, 2019,

Agent 2 arranged a final meeting with him at a hotel room in

Chicago, during which FBI agents arrested and took

Osadzinski into custody.

B

A month later a federal grand jury charged Osadzinski

with one count of knowingly attempting to provide material

support to a foreign terrorist organization by providing ser-

vices to ISIS in violation of 18 U.S.C. § 2339B.

Osadzinski moved to dismiss the indictment, arguing that

the charge was unconstitutionally vague because he lacked

fair notice that “downloading pro-ISIS media for personal

viewing and for potentially sharing with others online” might

qualify as a “service” to a terrorist organization under

§ 2339B. He also claimed that the application of § 2339B to his

conduct violated the First Amendment because he had en-

gaged only in protected expressive activity.

The government responded by proffering more details on

the nature of the services that Osadzinski had been indicted

for providing in support of ISIS. It described those services as:

[T]he creation or modification of [computer]

code, the establishment of Telegram channels in

which to utilize the code, the distribution of the

8 No. 22-3140

code to others in order to spread the ability to

preserve ISIS videos, and efforts to divert law

enforcement’s attention in order to protect the

code and the Telegram channels from law en-

forcement interference.

The district court denied Osadzinski’s motion. The court

concluded that the indictment, when considered in light of

the government’s bill of particulars, provided Osadzinski

with sufficient notice of the conduct for which he was being

prosecuted. Applying the Supreme Court’s decision in Holder

v. Humanitarian Law Project (HLP), the district court further

determined that Osadzinski—having developed his propa-

ganda-duplicating computer code in coordination with and at

the direction of ISIS—was not being prosecuted for expressive

activity shielded by the First Amendment.

The case then proceeded to trial. Over seven days, the gov-

ernment presented testimony from the five undercover FBI

operatives, an ISIS expert, and a computer science specialist.

Through those witnesses, the government introduced multi-

ple pieces of evidence, including screenshots of Osadzinski’s

online communications with agents, recordings of his conver-

sations with Agent 2, clips from ISIS videos found in his pos-

session, documents and other items obtained from his resi-

dence, and copies of his computer script. Osadzinski, as was

his right, presented no defense case.

The district court instructed the jury that, to find

Osadzinski guilty of violating 18 U.S.C. § 2339B, it needed to

find beyond a reasonable doubt that he had “knowingly at-

tempted to provide material support or resources” to ISIS in

the form of “services.” The district court then provided the

following instruction:

No. 22-3140 9

The term “services” refers to concerted activity,

not independent activity. Services provided as

material support to a foreign terrorist organiza-

tion include[] advocacy or activity performed in

coordination with, or at the direction of, a

foreign terrorist organization. Independent ac-

tivity or advocacy, however, is not prohibited.

At Osadzinski’s request, the district court further empha-

sized to the jury that nothing in the material-support statute

“abridge[s] the exercise of rights guaranteed under the First

Amendment” and, for that reason, “[a]dvocacy that is done

independently of the terrorist organization and not at its di-

rection or in coordination with it does not violate the statute.”

The jury returned a verdict of guilty. Osadzinski moved

for acquittal and alternatively for a new trial, challenging the

sufficiency of the government’s evidence. The district court

denied the motions, explaining that the government had pre-

sented ample evidence to permit the jury to find that

Osadzinski had knowingly attempted to engage in concerted

activity with ISIS to provide it with material support. The dis-

trict court sentenced Osadzinski to 90 months’ imprisonment,

below the advisory U.S. Sentencing Guidelines term of 240

months.

Osadzinski appealed, reiterating his First Amendment,

unconstitutional vagueness, and sufficiency-of-the-evidence

challenges.

II

Osadzinski’s First Amendment and constitutional vague-

ness challenges significantly merge and overlap. Both flow

from the same root contention that his conduct consisted

10 No. 22-3140

entirely of constitutionally protected independent advocacy.

We reject that contention, addressing each argument in turn.

A

We begin with the material support statute. By its terms,

18 U.S.C. § 2339B makes it a crime to “knowingly provid[e]

material support or resources to a foreign terrorist organiza-

tion.” Congress defined “material support or resources” as

“any property, tangible or intangible, or service.” 18 U.S.C.

§ 2339A(b)(1); see also id. § 2339B(g)(4). “Services” include

any “expert advice or assistance” that is “derived from scien-

tific, technical or other specialized knowledge.” Id.

§ 2339A(b)(1), (3).

The provision of material support must be “knowing”—

meaning a defendant must have “knowledge that the organi-

zation is a designated terrorist organization” or otherwise

“engages in terrorism” or “terrorist activity.” Id. § 2339B(a)(1).

Section 2339B does not require that support actually reach a

terrorist organization, however. The statute also prohibits

“attempt[ing]” to provide material support. Id. A defendant

“attempts” to commit a crime by taking a substantial step

towards its completion with the specific intent to follow

through. See United States v. Resendiz-Ponce, 549 U.S. 102,

106–07 (2007).

Section 2339B contains a constitutional savings clause:

“Nothing in this section shall be construed or applied so as to

abridge the exercise of rights guaranteed under the First

Amendment to the [U.S.] Constitution.” Id. § 2339B(i). Apply-

ing that clause, the Supreme Court in HLP explained that

§ 2339B did not prevent a person from freely speaking about,

or even independently advocating for, a terrorist

No. 22-3140 11

organization. See 561 U.S. at 24; see also Boim v. Quranic Liter-

acy Inst. and Holy Land Found. for Relief and Dev., 291 F.3d 1000,

1026 (7th Cir. 2002) (emphasizing the same point). Rather, the

Court made clear that the material-support statute prohibited

“only a narrow category of speech” that falls outside the

protection of the First Amendment—speech “to, under the di-

rection of, or in coordination with foreign groups that the

speaker knows to be terrorist organizations.” 561 U.S. at 26.

B

Drawing on HLP, Osadzinski claims that his conviction vi-

olated the First Amendment. He insists that the “services” he

allegedly provided ISIS consisted entirely of constitutionally

protected free expression. Allowing his conviction to stand

based on mere independent advocacy, he contends, would vi-

olate the Free Speech Clause.

For the sake of resolving this appeal, we accept

Osadzinski’s contention that all of his offense conduct quali-

fies as “speech” within the meaning of the First Amendment.

That includes several activities that have been recognized as

expression, such as writing an article and instruction manual,

forwarding multimedia links, and sending pro-ISIS messages

over social media. See Packingham v. North Carolina, 582 U.S.

98, 104–05, 108 (2017) (recognizing in a different context that

a person’s First Amendment right to “access [] places where

they can speak and listen” extends to social media). It also in-

cludes Osadzinski’s creation, execution, and distribution of

source code, which other circuits have found to constitute

“speech” under the First Amendment. See, e.g., Junger v.

Daley, 209 F.3d 481, 485 (6th Cir. 2000) (holding that source

code at a minimum is protected by the First Amendment);

Universal City Studios, Inc. v. Corley, 273 F.3d 429, 445–452 (2d

12 No. 22-3140

Cir. 2001) (holding that both object and source code qualify as

speech but that regulations thereof are content neutral so long

as they target only functional “nonspeech elements”).

This case does not require us to articulate the precise con-

tours of the First Amendment’s relationship with computer

code. The government appears to concede that all of

Osadzinski’s relevant conduct constitutes speech. We are

comfortable, therefore, assuming without definitively decid-

ing that Osadzinski’s offense conduct consisted entirely of ex-

pressive activity within the meaning of the First Amendment.

That observation does not end our analysis, however. To

say that Osadzinski engaged in expressive activity is not the

same as concluding that the First Amendment protected the

activity without qualification. The law has long recognized

that, in limited circumstances, speech may lose its full meas-

ure of constitutional protection and indeed violate the law.

See United States v. Stevens, 559 U.S. 460, 468 (2010) (explain-

ing that “[f]rom 1791 to the present, … the First Amendment

has permitted restrictions upon the content of speech in a few

limited areas” (cleaned up)); see also Eugene Volokh, Crime-

Facilitating Speech, 57 STAN. L. REV. 1095, 1132–36 (2005) (illus-

trating the difficulty of determining what categories of

expression should be subject to content-based restrictions

through the example of crime-facilitating speech). Take, for

example, incitements designed and likely to “produc[e] im-

minent lawless action,” which the Supreme Court declined to

shield from content-based restrictions in Brandenburg v. Ohio,

395 U.S. 444, 447–48 (1969). Or consider “true threats” of vio-

lence, which the Court likewise held to be a less protected cat-

egory of speech in Watts v. United States, 394 U.S. 705, 708

(1969); see also Virginia v. Black, 538 U.S. 343, 359 (2003)

No. 22-3140 13

(reiterating that the First Amendment does not fully protect

“true threats”—“statements where the speaker means to com-

municate a serious expression of an intent to commit an act of

unlawful violence to a particular individual or group of

individuals”).

The Supreme Court’s decision in HLP grounded itself in

these principles. The Court in no way questioned the right to

independently express personal views—positive, negative, or

neutral—about terrorist organizations. But it was equally

clear that the right has limits. One such limit is Congress’s

authority to prohibit expressive activity that amounts to the

provision of material support to a foreign terrorist organiza-

tion where the support is either addressed to, directed by, or

coordinated with that organization. See HLP, 561 U.S. at 26.

The jury found that Osadzinski had acted in coordination

with or under the direction of ISIS—which HLP determined

to fall outside the protection of the First Amendment. The

point is not subject to doubt, as the district court took care to

instruct the jurors not to return a guilty verdict unless they

concluded beyond a reasonable doubt that Osadzinski had

knowingly acted “in coordination with, or at the direction of,

a foreign terrorist organization.” The court further explained

that “[i]ndependent activity or advocacy [] is not prohibited”

and, in case any doubt remained, doubled down in a separate

instruction: “Advocacy that is done independently of the ter-

rorist organization and not at its direction or in coordination

with it does not violate the statute.” In returning its verdict,

the jury necessarily found that Osadzinski engaged in unpro-

tected expressive activity in concert with ISIS. On this record,

and having conducted our own independent legal review of

Osadzinski’s legal claims, we agree with the district court that

14 No. 22-3140

Osadzinski’s material-support conviction did not offend the

First Amendment.

Joined by amicus, Osadzinski presses an even broader le-

gal point. He objects that affirming his conviction would all

but eliminate the constitutional right to independently advo-

cate for a terrorist organization. Osadzinski highlights that, if

a group’s general call for support is enough to constitute “di-

rection” under HLP, then anyone who watches a video like

Inside 8 would subsequently be barred from engaging in core

First Amendment activity—viewing and sharing others’

viewpoints—simply because the terrorist group asks its sup-

porters to do so.

Osadzinski is right on a broad level. Any holding that

would eliminate—explicitly or otherwise—a person’s right to

engage in independent advocacy for a terrorist organization

would conflict with long-recognized constitutional princi-

ples. We have observed that section 2339B does not prohibit

persons from expressing sympathy for the views of a foreign

terrorist organization. See Boim, 291 F.3d at 1026. We reject

any interpretation of “coordination” or “direction” that

would prohibit expressive activity aligned with that view.

But Osadzinski’s baseline assumption is mistaken. He was

not convicted simply for watching Inside 8 and subsequently

engaging in what would otherwise constitute independent

advocacy. Far from it. At every step, Osadzinski closely coor-

dinated his activity with ISIS and its media office by contrib-

uting to official videos and providing them with a software

tool to organize, duplicate, and disseminate media to a wider

audience while circumventing censors. Our affirming his con-

viction respects these legal lines.

No. 22-3140 15

C

Osadzinski brings a separate but related legal challenge,

invoking the Due Process Clause of the Fifth Amendment and

contending that § 2339B was unconstitutionally vague as ap-

plied to his offense conduct. He acknowledges that the

Supreme Court in HLP rejected a similar vagueness challenge,

holding that § 2339B clearly barred nonprofits from advising

terrorist organizations on international law. See 561 U.S. at

21–22. But he argues that, while § 2339B certainly has some

clear applications, the statute is vague regarding whether it

extends to his particular offense conduct. Put another way,

Osadzinski insists that he lacked reasonable notice that his

specific actions might constitute “services” to ISIS as that term

is used in § 2339B.

“A conviction fails to comport with due process if the stat-

ute under which it is obtained fails to provide a person of

ordinary intelligence fair notice of what is prohibited, or is so

standardless that it authorizes or encourages seriously dis-

criminatory enforcement.” United States v. Williams, 553 U.S.

285, 304 (2008). The “touchstone” of fair notice “is whether the

statute, either standing alone or as construed, made it reason-

ably clear at the relevant time that the defendant’s conduct

was criminal.” United States v. Lanier, 520 U.S. 259, 267 (1997).

When a statute “interferes with the right of free speech or

of association, a more stringent vagueness test should apply.”

Vill. of Hoffman Estates v. Flipside, Hoffman Estates, Inc., 455 U.S.

489, 499 (1982). Yet “perfect clarity and precise guidance have

never been required.” Williams, 553 U.S. at 304 (internal quo-

tation marks omitted). So long as a statute “clearly

proscribe[s]” a defendant’s conduct, it is not unconstitution-

ally vague, even to the extent a heightened standard may

16 No. 22-3140

apply. See HLP, 561 U.S. at 20 (citing and relying on the rea-

soning of Hoffman Estates).

When assessing a vagueness challenge to a criminal con-

viction, we construe the defendant’s conduct in light of “[t]he

trial record, read most favorably to the jury’s verdict.” See La-

nier, 520 U.S. at 261. Here, the record makes clear that

Osadzinski engaged in conduct “clearly proscribed” by

§ 2339B. For that reason, his vagueness challenge fails.

We have no difficulty concluding that Osadzinski’s ac-

tions qualified as a “service” that materially supported ISIS.

See 18 U.S.C. § 2339A(b)(1). Recall that the statute defines

“service” to include “expert advice or assistance” “derived

from scientific, technical or other specialized knowledge.” Id.

§ 2339A(b)(1), (3). Osadzinski provided exactly that. He used

his computer training to create and deploy a computer script

that duplicated troves of ISIS propaganda to circumvent the

censorship of ISIS media online. He then instructed other ISIS

supporters on how to use the script to achieve the same objec-

tive. In doing so, he provided material support to ISIS (and its

media campaign) within the meaning of § 2339B.

The trial evidence shows beyond any dispute that

Osadzinski performed these actions “knowingly”—fully un-

derstanding that ISIS “has engaged or engages in terrorist ac-

tivity.” Id. § 2339B(a)(1). In scores of communications with the

undercover FBI operatives, Osadzinski demonstrated an

awareness of ISIS’s mission and violent terrorist activities. In

one exchange, he sent Agent 3 an official ISIS video that cul-

minated in a montage of beheadings and commented, “the

end is the best.” We need say no more on this point.

No. 22-3140 17

Osadzinski emphasizes that the term “service” in § 2339B,

as construed in HLP, extends only to concerted speech activ-

ity—that which is addressed to, coordinated with, or directed

by ISIS. Again, we accept Osadzinski’s base assumption that

his offense conduct entailed expressive activity. We nonethe-

less conclude that his conduct unambiguously qualifies as

concerted activity.

HLP did not present the Supreme Court with an occasion

to drill down into how much “coordination” or “direction” is

required to amount to the provision of “services” within the

meaning of § 2339B. See 561 U.S. at 25 (holding that “grada-

tions of fact or charge would make a difference as to criminal

liability, and so adjudication of the reach [of § 2339B] must

await a concrete fact situation” (cleaned up)). The line divid-

ing concerted conduct from independent advocacy will

doubtless emerge as courts continue to consider challenges to

convictions under § 2339B. We need only decide whether

Osadzinski’s conduct clearly falls on the proscribed side of

that line.

It did. Osadzinski acted in response to what he perceived

to be a solemn directive from ISIS contained in the Inside 8

video: “Support your khilafah on the digital front” by

“adopt[ing] the messaging put out by its official media,” and

“striv[ing] to disseminate it far and wide.” In discussions with

the undercover law enforcement agents, he explicitly refer-

enced Inside 8’s directive: “[I]f they close one account, open

another three. And if they close three, open another 30.” And

he sought to do just that.

For months, Osadzinski labored diligently to answer

ISIS’s call for help in waging its media campaign. He assisted

ISIS’s media offices by contributing English subtitles and a

18 No. 22-3140

voiceover to their videos. He compiled and organized a mas-

sive database of high-resolution ISIS videos for future distri-

bution. He designed a program to automatically organize and

multiply ISIS content online. And he taught fellow ISIS sup-

porters how to do the same, spending hours over several days

to assist with troubleshooting. Through these actions,

Osadzinski propelled himself far beyond the role of an inde-

pendent advocate, effectively fusing his voice with that of

ISIS’s media bureaus by improving, contributing to, compil-

ing, organizing, and designing a tool to explosively distribute

their official publications.

Throughout, Osadzinski coordinated his actions—or, at

the very least, attempted to coordinate them—with ISIS mem-

bers. At least twice he reiterated to Agent 3, “[i]f any brothers

need help with security, tell them to come to me.” When

Agent 1 offered to put Osadzinski in touch with ISIS’s official

media bureau, he replied that he hoped to do so “in the near

future.” He later invited Agent 3 to share his ISIS media chan-

nels with “anyone [he] trusted.” When Agent 2 requested

guidance on how to run the computer program that he could

take back to ISIS members, Osadzinski did not hesitate. He

even wrote a step-by-step instructional guide for any ISIS

follower to use.

Osadzinski planned to go even further. He explained to

Agent 3 that he intended to convert his comprehensive ar-

chive of ISIS videos into a torrent that could be spread widely

with minimal risk of censorship. He even suggested working

in tandem with ISIS’s official media bureaus to help them

organize their online content. Through the dissemination and

deployment of his code, Osadzinski hoped that “the brothers

who have access to the disorganized al-Furat Media and al-

No. 22-3140 19

Hayat Media Center channels will be able to organize them or

give me access to them so that I would be able to organize

them.” Those are not the words of an unassociated or inde-

pendent advocate. They are more suggestive of what

Osadzinski had at that point become: a self-deputized IT

servicer for the Islamic State.

Osadzinski highlights that at one point in June 2018 he de-

clined Agent 3’s invitation to connect with ISIS members.

While true, Osadzinski explained that he did so only because

he knew he was being watched by the FBI. As soon as he be-

lieved the surveillance had ended, he resumed coordination

with ISIS. By August 2019, he proclaimed that “they gave up

following me” so “now I am making as much jihad as possi-

ble.” That comment, compounded by dozens of others like it,

reflects Osadzinski’s expressed intent to coordinate with ISIS.

Taken together, the totality of the record refutes

Osadzinski’s claim that he had no idea his conduct might vi-

olate § 2339B. Time and time again, Osadzinski took concrete

action in direct response to ISIS’s call for help to combat

online censorship. He did so in attempted coordination with

ISIS’s official media bureau and members with the expressed

intent for that coordination to deepen. Such conduct is incon-

sistent with independent advocacy and is proscribed by

§ 2339B.

In the final analysis, then, Osadzinski’s vagueness chal-

lenge fails for the same core reason as his First Amendment

claim: he attempted to engage in activity coordinated with or

directed by a known foreign terrorist organization. Such ac-

tivity is both unprotected by the First Amendment and clearly

violative of § 2339B. We see no unconstitutional vagueness in

allowing the material-support conviction to stand.

20 No. 22-3140

III

Osadzinski directs his final challenge to the sufficiency of

the evidence presented at his trial. He contends that the jury

lacked an adequate basis to find him guilty because the evi-

dence did not establish his specific intent to coordinate with

or receive direction from ISIS.

Evidence is sufficient to support a conviction so long as

“any rational trier of fact could have found the essential ele-

ments of the crime beyond a reasonable doubt” after “viewing

the evidence in the light most favorable to the prosecution.”

Jackson v. Virginia, 443 U.S. 307, 319 (1979); see also United

States v. Norwood, 982 F.3d 1032, 1039 (7th Cir. 2020) (holding

that a verdict should be overturned for insufficient evidence

only if “the record contains no evidence, regardless of how it

is weighted, from which the jury could have found guilt be-

yond a reasonable doubt”). We have interpreted this standard

as creating a “nearly insurmountable hurdle” on the part of

the defendant challenging the sufficiency of the evidence.

United States v. Johnson, 874 F.3d 990, 998 (7th Cir. 2017)

(cleaned up). Osadzinski cannot overcome it.

Viewed in the light most favorable to the government, the

record contains sufficient evidence demonstrating

Osadzinski’s intent to act in coordination with or at the direc-

tion of ISIS. Id. Jurors saw messages Osadzinski sent to Agent

3 inviting him to connect him with ISIS brothers. They also

heard testimony from Agent 2, who shared how Osadzinski

taught him the computer program so he could relay the infor-

mation back to ISIS members. And they read the Heralds of

the Internet guide that Osadzinski authored, where he sug-

gested that ISIS’s media bureaus should give him access to

their official channels for him to organize.

No. 22-3140 21

These statements provide a sufficient basis for a rational

jury to conclude that Osadzinski aimed to coordinate his ac-

tivity with ISIS. Indeed, the record indicates that such coordi-

nation was his overarching goal. As Osadzinski explained to

Agent 3, by multiplying ISIS content online through his com-

puter script, he hoped to distract Western intelligence agen-

cies and give ISIS supporters more time to “plan[] attacks”

without “being spied on.”

The jury had a more than sufficient basis to conclude that

Osadzinski provided services to ISIS, in coordination with

ISIS, or under ISIS’s direction.

IV

At their core, Osadzinski’s First Amendment, vagueness,

and sufficiency challenges fail for the same overarching

reason: his conduct, as proved by the evidence presented to

the jury, went beyond constitutionally protected independent

advocacy and crossed the line into prohibited concerted ac-

tivity at the behest of a known foreign terrorist organization—

ISIS. Osadzinski and the amicus raise important concerns

about the challenge of drawing that line in a manner that re-

spects the foundational right to free expression. While those

concerns do not support reversal in this case, they will doubt-

less persist as future courts endeavor to chart the border be-

tween protected speech and material support. Today we

simply decide that Thomas Osadzinski’s conduct fell outside

the protection of the First Amendment, unambiguously vio-

lated § 2339B, and permitted a reasonable jury to return a

guilty verdict.

We AFFIRM.