Court Opinion

ID: 9955586
Source: CourtListenerOpinion
Date Created: 2024-03-28 20:01:28.890744+00
Date Added: 2024-06-11T08:15:06.618209
License: Public Domain

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.
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    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.