United States of America v. Donald Dorosheff

In the
United States Court of Appeals
for the Seventh Circuit
____________________
No. 22-2291
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
v.
DONALD DOROSHEFF,
Defendant-Appellant.
____________________
Appeal from the United States District Court
for the Central District of Illinois.
No. 16-CR-30049-001 — Sue E. Myerscough, Judge.
____________________
ARGUED MAY 23, 2023 — DECIDED AUGUST 6, 2024
____________________
Before SYKES, Chief Judge, and BRENNAN and PRYOR,
Circuit Judges.
SYKES, Chief Judge. This case is one of many prosecutions
arising from an extensive investigation of a dark-web child-
pornography website known as “Playpen.” The FBI gained
control of the website’s servers in 2015 and obtained a
warrant to deploy a sophisticated computer program—in the
agency’s jargon, a “Network Investigative Technique” or
“NIT” for short—to penetrate the dark web’s anonymizing

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2 No. 22-2291
features and unmask hundreds of Playpen users. With those
identities in hand, agents obtained additional warrants to
search the residences and computers of the website’s users
across the country.
Donald Dorosheff is one of many Playpen users who
were identified using the NIT program. A resident of
Springfield, Illinois, he was charged in the Central District of
Illinois with receiving and possessing child pornography.
He sought to suppress the evidence recovered from his
digital devices after he was unmasked. Like other Playpen
defendants, he argued that the judicial officer who issued
the NIT warrant—a magistrate judge in the Eastern District
of Virgina—lacked the authority under Rule 41 of the Feder-
al Rules of Criminal Procedure to authorize an electronic
search extending outside her district. That lack of authority,
he contended, meant that the subsequent searches of his
devices violated the Fourth Amendment. The district judge
agreed that Rule 41 did not authorize the issuance of the
extraterritorial NIT warrant but applied the good-faith
exception and declined to suppress the evidence.
We have twice affirmed the application of the good-faith
exception to evidence obtained in searches flowing from the
Playpen NIT warrant. See United States v. Grisanti, 943 F.3d
1044 (7th Cir. 2019); United States v. Kienast, 907 F.3d 522 (7th
Cir. 2018). Here Dorosheff raises a new argument based on
the Justice Department’s support for an amendment to Rule
41 expressly authorizing magistrate judges to issue this kind
of warrant. This evidence, he insists, demonstrates that high-
ranking Department officials knew that the Playpen NIT
warrant was invalid, and their knowledge should be imput-

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No. 22-2291 3
ed to the FBI agent who applied for the warrant, thus defeat-
ing the good-faith exception.
This argument is new for us but other circuits have ad-
dressed and uniformly rejected it. We join the consensus and
adhere to our precedent that evidence derived from the
Playpen NIT warrant is admissible under the good-faith
exception to the exclusionary rule.
I. Background
Playpen was a global online forum that enabled users to
access, distribute, and discuss child pornography. Because
the website existed on the dark web, a user had to download
an anonymizing software called “Tor” before accessing it.
Tor hid the identities of users by preventing websites from
registering the Internet Protocol (“IP”) addresses of access-
ing computers. With that software installed, a user could join
Playpen by obtaining the site’s unique web address—a
random sequence of numbers and letters—and signing up
with a username and password.
FBI agents arrested Playpen’s administrator and gained
control of the servers in early 2015. But the FBI did not
immediately shut the website down. Instead, as part of
Operation Pacifier, Special Agent Douglas Macfarlane
submitted a warrant application and supporting affidavit to
a magistrate judge in the Eastern District of Virginia. Those
documents described Playpen, Tor, and the government’s
investigation in detail. They also explained the government’s
plan for unmasking Playpen users with the NIT.
Although the NIT was sophisticated, the proposed plan
was straightforward. The FBI would keep Playpen running
for a limited time. When a user accessed the website, the NIT

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4 No. 22-2291
would send instructions to that user’s computer telling it to
transmit its IP address and other identifying information to a
government-controlled computer. The warrant application
made clear that this identifying information could be seized
“[f]rom any ‘activating’ computer,” meaning any computer
that logged into Playpen. And the affidavit stated that the
NIT “may cause” activating computers “wherever located”
to send that information to the government.
The magistrate judge issued the NIT warrant in February
2015. During the short time that Playpen remained opera-
tional, a user accessed the website under the name “Grite.”
The IP address associated with that account belonged to
Donald Dorosheff, a resident of Springfield, so an FBI agent
in Illinois sought and obtained a warrant to search his
apartment and any computers and computer media (like
digital storage devices) inside. Agents found one video and
over 1,100 images of child pornography on Dorosheff’s
digital devices.
Dorosheff was charged with two counts of receiving
child pornography, 18 U.S.C. § 2252A(a)(2)(A) and (b)(1),
and two counts of possessing child pornography, id.
§ 2252A(a)(5)(B) and (b)(2). He moved to suppress the
evidence recovered from his digital devices on the basis that
the NIT warrant—which led to the Illinois warrant—was
invalid because the Virginia magistrate judge lacked the
authority under Rule 41(b) to issue a warrant for a search of
this type outside her district. See FED. R. CRIM. P. 41(b) (2015)
(describing a magistrate judge’s authority to issue warrants).

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No. 22-2291 5
The district judge denied the suppression motion.1 She
found that the NIT warrant was supported by probable
cause but agreed with Dorosheff that the magistrate judge
had exceeded the scope of her authority under Rule 41(b) to
issue a warrant to search property outside her district. The
judge determined, however, that the evidence recovered in
the search of Dorosheff’s devices was admissible under the
good-faith exception to the exclusionary rule. She reasoned
that suppression wouldn’t deter police misconduct because
the extent of the magistrate judge’s authority under the rule
was a difficult and contested legal question, and the officers
who obtained and executed the Playpen NIT warrant acted
in an objectively reasonable manner in relying on the judge’s
assessment of the law. Dorosheff moved for reconsideration,
but the judge declined to alter her decision.
Dorosheff later filed a second suppression motion raising
a new argument aimed directly at the application of the
good-faith exception. He argued that senior officials at the
Department of Justice (“DOJ” or “the Department”) knew
that the NIT warrant would violate Rule 41(b) at the time
Agent Macfarlane applied for it. To support this sweeping
claim, Dorosheff highlighted the DOJ’s advocacy of an
amendment to Rule 41(b) that would expressly authorize
this kind of remote electronic search warrant. The Depart-
ment’s pursuit of the amendment, he suggested, was evi-
dence that high-ranking DOJ officials knew that the NIT
warrant was invalid, and under the collective-knowledge
1 Dorosheff’s first motion also challenged the Illinois warrant. But the
judge rejected his arguments about that warrant because the affidavit set
forth sufficient facts to establish probable cause.

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6 No. 22-2291
doctrine, this knowledge should be imputed to the agents on
the ground who were involved in the warrant application.
The judge rejected this argument and denied the second
suppression motion. She noted that the good-faith exception
considers the “culpability of the officers who obtain and
execute the warrant,” not the government writ large. And
Dorosheff had failed to connect any of the high-ranking
officials involved in the Rule 41 amendment process to the
Playpen NIT warrant application. As before, the judge ruled
that the evidence recovered from Dorosheff’s devices was
admissible under the good-faith exception because suppres-
sion would not meaningfully deter culpable law-
enforcement conduct.
The case then proceeded to trial. Dorosheff waived his
right to a jury and the case was tried to the court. The judge
found Dorosheff guilty on all counts and imposed sentence.
This appeal followed.2
II. Discussion
Dorosheff challenges only the judge’s denial of his sup-
pression motions. We review the judge’s legal conclusions de
novo and her findings of fact for clear error. United States v.
James, 571 F.3d 707, 713 (7th Cir. 2009). As in Kienast and
Grisanti, we take no position on the merits of the underlying
Rule 41(b) and Fourth Amendment questions; here, as in
those cases, our focus is on the good-faith exception to the
2 We appointed Attorney Robert J. Palmer to represent Dorosheff
pursuant to the Criminal Justice Act. He supervised law student Shane
Coughlin of the University of Notre Dame Law School, who assisted him
on this appeal. They have ably discharged their duties. We thank them
for their service to their client and the court.

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No. 22-2291 7
exclusionary rule. Dorosheff has not given us a good reason
to depart from our prior cases holding that the good-faith
exception applies to evidence recovered in searches flowing
from the Playpen NIT warrant.
Because we’ve addressed this specific issue twice before,
we can be brief. The exclusionary rule is a judge-made
remedy “meant to deter future Fourth Amendment viola-
tions,” Kienast, 907 F.3d at 527, but suppressing evidence is a
“last resort, not [a] first impulse,” Hudson v. Michigan, 547
U.S. 586, 591 (2006). We apply the exclusionary rule only
when its deterrence benefits “outweigh its substantial social
costs.” Id. (internal quotation marks omitted). Crucially, the
deterrence side of the equation focuses exclusively on “cul-
pable law enforcement conduct.” Davis v. United States, 564
U.S. 229, 246 (2011). That’s what suppression must meaning-
fully deter for the remedy to be appropriate. And that’s why
suppressing evidence is inappropriate when doing so would
“[p]enaliz[e] the officer for the magistrate’s error[] rather
than his own.” United States v. Leon, 468 U.S. 897, 921 (1984).
So when a law-enforcement officer acts within the scope of a
warrant obtained in “objective good faith … from a judge or
magistrate, … the good-faith exception generally applies
even if the warrant turns out to be invalid.” Grisanti, 943 F.3d
at 1049 (internal quotation marks omitted).
These limits on the exclusionary rule explain why we
have twice rejected efforts to suppress evidence derived
from the NIT warrant. In Kienast several Playpen defendants
argued that the good-faith exception is categorically inappli-
cable when a judge lacks authority to issue a particular
warrant but does so anyway. 907 F.3d at 527. We bypassed
the complicated underlying legal questions about the magis-

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8 No. 22-2291
trate judge’s authority under Rule 41(b); assuming for the
sake of argument that the judge improperly issued the
Playpen NIT warrant, we did not see how that flaw differed
from other kinds of judicial errors. Id. at 528. Suppressing
evidence because the magistrate judge misunderstood the
scope of her authority—just like suppressing evidence
because the magistrate erred in assessing probable cause—
would “[p]enaliz[e] the officer for the magistrate’s error.” Id.
(quoting Leon, 468 U.S. at 921) (first alteration in original).
We also rejected the defendants’ argument that “the of-
ficers should have known that the magistrate judge lacked
authority to issue” the NIT warrant. Id. Whether the warrant
was consistent with Rule 41(b) “pose[d] difficult conceptual
questions”; that much was clear from the split that had
emerged among district courts on the issue. Id. at 528–29. So
if the magistrate judge made a mistake about the scope of
her authority, that “would not necessarily have been obvious
to the officers.” Id. at 529.
A year later another Playpen defendant in our circuit
tried to distinguish Kienast and avoid the good-faith excep-
tion. He primarily argued that Agent Macfarlane obtained
the warrant in bad faith because his affidavit suggested that
all searches would take place in the magistrate judge’s
district. Grisanti, 943 F.3d at 1050. We rejected this argument
too. The affidavit described the NIT and stated that it could
recover information from computers “wherever located” if
those computers accessed Playpen. Id. (emphasis added).
And Agent Macfarlane gave the judge “ample information”
to enable follow-up questions about the warrant’s geograph-
ic scope—and about the potential legal implications of that
scope. Id. at 1051.

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No. 22-2291 9
Ten other circuits have encountered appeals stemming
from the Playpen NIT warrant. Some have ventured into the
difficult underlying Rule 41(b) and Fourth Amendment
issues. See, e.g., United States v. Taylor, 935 F.3d 1279, 1285–88
(11th Cir. 2019) (holding that the magistrate judge’s issuance
of the NIT warrant violated Rule 41(b) and that subsequent
searches violated the Fourth Amendment). All have applied
the good-faith exception.3 The common theme is one we
expressed in Kienast: The legal issues surrounding Rule 41(b)
were complex and unsettled when Agent Macfarlane applied
for the NIT warrant, so the agents involved acted reasonably
by presenting a detailed affidavit and deferring to the magis-
trate judge’s resolution of any legal questions implicated by
the warrant. See, e.g., United States v. Levin, 874 F.3d 316, 323
(1st Cir. 2017) (“We see no benefit in deterring such con-
duct—if anything, such conduct should be encouraged[]
because it leaves it to the courts to resolve novel legal is-
sues.”); Taylor, 935 F.3d at 1292 (explaining that given the
“complex new technology at issue,” the officers “did what
we would hope and expect—they fully disclosed the me-
chanics of the intended search, left the constitutional call to
the magistrate judge, and acted in reasonable reliance on the
resulting warrant”). And because any error resulting from
3 See United States v. Levin, 874 F.3d 316, 321–24 (1st Cir. 2017); United
States v. Eldred, 933 F.3d 110, 118–21 (2d Cir. 2019); United States v.
Werdene, 883 F.3d 204, 215–18 (3d Cir. 2018); United States v. McLamb,
880 F.3d 685, 690–91 (4th Cir. 2018); United States v. Ganzer, 922 F.3d 579,
584–90 (5th Cir. 2019); United States v. Moorehead, 912 F.3d 963, 967–71
(6th Cir. 2019); United States v. Horton, 863 F.3d 1041, 1049–52 (8th Cir.
2017); United States v. Henderson, 906 F.3d 1109, 1117–20 (9th Cir. 2018);
United States v. Workman, 863 F.3d 1313, 1317–21 (10th Cir. 2017); United
States v. Taylor, 935 F.3d 1279, 1288–93 (11th Cir. 2019).

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10 No. 22-2291
those difficult legal questions was made by the magistrate
judge rather than by the officers, the “benefits of deterrence
cannot outweigh the costs” of suppression. United States v.
Moorehead, 912 F.3d 963, 971 (6th Cir. 2019) (internal quota-
tion marks omitted).
Dorosheff offers a new argument centering on the DOJ’s
advocacy of an amendment to Rule 41(b) expressly authoriz-
ing magistrate judges to issue warrants like this one. These
efforts, he contends, demonstrate that high-ranking Depart-
ment officials knew that warrants of this type were invalid at
the time, undermining our conclusions in Grisanti and
Kienast that the good-faith exception applies to searches
flowing from the Playpen NIT warrant. For additional
support, he points to In re Warrant to Search a Target Computer
at Premises Unknown, 958 F. Supp. 2d 753, 756–58 (S.D. Tex.
2013), in which a magistrate judge determined that a similar
remote-access warrant exceeded his authority under Rule
41(b). As Dorosheff sees it, this evidence demonstrates that
DOJ officials were aware that Rule 41(b) as then written did
not authorize warrants of this type; he urges us to apply the
“collective knowledge” doctrine and impute their
knowledge of Rule 41(b)’s limits to the agents involved in the
Playpen NIT warrant process.
Our colleagues in other circuits have uniformly rejected
this argument, explaining that it rests on the flawed premise
that the DOJ’s support for an amendment to Rule 41(b)
amounts to an “admission” that remote-access warrants like
the Playpen NIT warrant were beyond the scope of the then-
existing rule; our sister circuits have instead recognized that
the Department’s push for an amendment was simply “an
attempt to clarify an existing [rule’s] application to new

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No. 22-2291 11
circumstances.” United States v. Ganzer, 922 F.3d 579, 589 (5th
Cir. 2019); see also Taylor, 935 F.3d at 1292 n.14 (“We see no
benefit to deterring officers from attempting to describe
cutting-edge countermeasures using the forms and resources
at their disposal while department heads simultaneously
seek to amend the rules to better address advancing technol-
ogy.”); United States v. Eldred, 933 F.3d 110, 119–20 (2d Cir.
2019) (rejecting the argument that the amendment efforts
and communications about such efforts render the good-
faith exception inapplicable); United States v. Cookson, 922
F.3d 1079, 1088–90 (10th Cir. 2019) (same); Moorehead, 912
F.3d at 970 (same); United States v. Werdene, 883 F.3d 204, 218
nn.11–12 (3d Cir. 2018) (same).
We agree with this reasoning. The DOJ’s effort to amend
Rule 41 does not undermine the application of the good-faith
exception to derivative evidence from the Playpen NIT
warrant. The DOJ’s advocacy for a change in the rule shows
only that the Department was aware of an unsettled legal
issue and had urged the judiciary to update the rule to
address more explicitly the special circumstances that arise
when dealing with cutting-edge technology in the digital
age. Cookson, 922 F.3d at 1089.
Indeed, as reflected in the 2013 letter from the Acting As-
sistant Attorney General to the Judicial Conference’s Adviso-
ry Committee on Criminal Rules, the DOJ proposed that the
rules committee consider amending Rule 41(b) to “clarify the
procedural rules” that law-enforcement agents should
follow when pursuing similar warrants. The Advisory
Committee agreed, and the rule was eventually revised. But
the “proposed and actual amendment” of Rule 41(b) “bear[s]
no clear indications that the pre-amendment Rule 41 forbade

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12 No. 22-2291
the NIT warrant, let alone that the FBI knew as much.”
Cookson, 922 F.3d at 1090. Rather, the amendment history
confirms what 11 circuits—including ours—have concluded:
the scope of Rule 41(b) was simply “unclear at the time the
NIT warrant issued,” id., so the agents involved in the
investigation sensibly left the difficult legal questions to the
magistrate judge and acted in good-faith reliance on the
resulting warrant.
Nor does a single decision from a magistrate judge in
Texas support Dorosheff’s claim that DOJ officials knew the
NIT warrant exceeded the scope of the old Rule 41(b). Id. at
1089; see also Werdene, 883 F.3d at 218 n.12. The 2013 In re
Warrant decision might have alerted them to the uncertain
legal landscape, but it hardly conclusively settled the issue.
Dorosheff’s argument suffers from an additional flaw. He
contends that the collective-knowledge doctrine requires us
to impute the (supposed) knowledge of high-ranking DOJ
officials to the FBI agents involved in the NIT warrant
process. This argument misunderstands the doctrine, which
permits a law-enforcement officer to rely on facts supplied
by other officers to support a “stop, search, or arrest [of] a
suspect … even if the officer himself” lacks “firsthand
knowledge of facts that amount to the necessary level of
suspicion.” United States v. Williams, 627 F.3d 247, 252 (7th
Cir. 2010); see also United States v. Ellis, 499 F.3d 686, 690 (7th
Cir. 2007) (explaining that “[t]his doctrine permits arresting
officers to rely on the knowledge … of other officers” who
communicate that knowledge). The doctrine recognizes that
police “must often act swiftly” in response to developing
circumstances and “cannot be expected to cross-examine
their fellow officers” about the information transmitted to

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No. 22-2291 13
them in an ongoing investigation. United States v. Harris, 585
F.3d 394, 400 (7th Cir. 2009) (quoting United States v. Hensley,
469 U.S. 221, 231 (1985)).
The collective-knowledge doctrine has no application in
this context. The good-faith inquiry turns on the “objective
reasonableness” of the actions of the officers who participat-
ed in the warrant application and subsequent search—that
is, those “who eventually executed a warrant,” “who origi-
nally obtained it,” and “who provided information material
to the probable-cause determination.” Leon, 468 U.S. at 923
n.24. The good-faith exception applies here because the
agents involved in obtaining and executing the Playpen NIT
warrant reasonably relied on the magistrate judge’s determi-
nation of her authority under Rule 41(b).
Dorosheff also points out that Agent Macfarlane did not
use the agency’s specialized warrant application form for a
so-called “tracking device” warrant, which magistrate
judges may issue in some circumstances under Rule 41(b)(4).
See Taylor, 935 F.3d at 1286. The government argues, as it has
before, that Rule 41(b)(4) authorized the Playpen NIT war-
rant because the NIT qualified as a type of “tracking device”
designed to “track the movement of a person or property
located within … [or] outside the [judge’s] district.” FED. R.
CRIM. P. 41(b)(4). In Dorosheff’s view, Agent Macfarlane’s use
of a general warrant application form—instead of a “track-
ing device” application form—is evidence that he knew that
the warrant he was seeking exceeded the magistrate judge’s
Rule 41 authority.
The argument about the form is a red herring, as five cir-
cuits have recognized. See Taylor, 935 F.3d at 1285–86, 1293;
Moorehead, 912 F.3d at 970–71; Werdene, 883 F.3d at 211, 218;

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14 No. 22-2291
United States v. McLamb, 880 F.3d 685, 690–91 (4th Cir. 2018);
Workman, 863 F.3d at 1320–21. The proper inquiry is not
which form was used but whether the agents involved
“act[ed] with an objectively reasonable good-faith belief that
their conduct [was] lawful.” Kienast, 907 F.3d at 527 (quoting
Davis, 564 U.S. at 238).
Agent Macfarlane applied for a complex warrant involv-
ing sophisticated technology to counteract the unique inves-
tigative difficulties posed by the dark web. His job was to
provide a neutral magistrate judge with accurate details
about this technology, the investigation, and the proposed
search so that the judge could decide any relevant legal
issues. That’s what he did. See McLamb, 880 F.3d at 690
(“Although he does not specifically use the term ‘tracking
device’ in his affidavit, Agent Macfarlane’s detailed descrip-
tion of the NIT was sufficient to inform the magistrate judge
of the scope of the warrant sought.”); Levin, 874 F.3d at 323
(noting that Agent Macfarlane’s “detailed affidavit” de-
scribed the “investigation, including how the NIT works,”
and information about the proposed searches).
Suppressing evidence because law enforcement used a
general rather than specialized warrant application form
would not serve the limited purpose of the exclusionary
rule: the deterrence of “sufficiently deliberate” and “suffi-
ciently culpable” police conduct. Herring v. United States,
555 U.S. 135, 144 (2009). In short, we agree with the Eleventh
Circuit: “[T]he officers did the best they could with what
they had—a general application form that was perhaps ill-
suited to the complex new technology at issue.” Taylor, 935
F.3d at 1292. This case does not implicate deliberately culpa-

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No. 22-2291 15
ble police conduct, so the “benefits of suppression” do not
“outweigh its heavy costs.” Davis, 564 U.S. at 237.
AFFIRMED

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