As the build up to the Ross Ulbrict's appellate hearing continues, the National Association of Criminal Defense Lawyers has filed an amicus brief criticizing the unconstitutionality of the investigation which lead to the persecution of Ross Ulbricht. The move comes as militia operations motivated by other breaches of the United States constitution by the Federal government have resulted in the liberation of substantial portions of Oregon. Whether the appellate court follows Judge Katherine Forrest in rejecting sanity and constitutional limits remains to be seen.

Full text of the amicus filing is available as plaintext below or as a pdf here:

Case 15-1815, Document 45, 01/19/2016, 1686497, Page1 of 40

15-1815
___________________________________________________
UNITED STATES COURT OF APPEALS
FOR THE
SECOND CIRCUIT
_____________________________
UNITED STATES OF AMERICA, Appellee,
-v.ROSS WILLIAM ULBRICHT, AKA DREAD PIRATE ROBERTS, AKA
SILK ROAD, AKA SEALED DEFENDANT 1, AKA DPR, DefendantAppellant.
_____________________________
ON APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE SOUTHERN DISTRICT OF NEW YORK
_____________________________
AMICUS CURIAE BRIEF OF THE NATIONAL ASSOCIATION
OF CRIMINAL DEFENSE LAWYERS IN SUPPORT OF
DEFENDANT-APPELLANT AND ARGUING REVERSAL
_____________________________
STEVEN R. MORRISON
UNIVERSITY OF NORTH DAKOTA
SCHOOL OF LAW
1526 Robertson Court
Grand Forks, North Dakota 58201
(617) 749-7817

JOEL B. RUDIN
LAW OFFICES OF JOEL B.
RUDIN, P.C.
600 Fifth Avenue, 10th Floor
New York, NY 10020
(212) 752-7600

Vice Chair, NACDL Amicus
Curiae Committee

Vice Chair, NACDL Amicus
Curiae Committee

Case 15-1815, Document 45, 01/19/2016, 1686497, Page2 of 40

CORPORATE DISCLOSURE STATEMENT
Amicus curiae National Association of Criminal Defense Lawyers
(“NACDL”) submits the following corporate disclosure statement, as required
by Fed. R. App. P. 26.1 and 29(c): NACDL is a nonprofit corporation
organized under the laws of the District of Columbia. It has no parent
corporation, and no publicly held corporation owns ten percent or more of its
stock.
Dated: January 19, 2016
Grand Forks, North Dakota

Steven R. Morrison
Steven R. Morrison
Attorney for Amicus Curiae National Association of
Criminal Defense Lawyers

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TABLE OF CONTENTS
Item

Page

CORPORATE DISCLOSURE STATEMENT …………………………………….i
TABLE OF CONTENTS……………………………………………………………………..ii
TABLE OF AUTHORITIES ……………………………………………………………… iii
STATEMENT OF IDENTITY, INTEREST, AND AUTHORITY . viii
ARGUMENT ………………………………………………………………………………………. 1
I.

The warrants issued in this case lacked a limiting
statement of particularity and were therefore
unconstitutional, violating the original intent of the
Fourth Amendment, extant historical and contemporary
jurisprudence, and this Court’s case law ……………………………….. 1
A. Introduction ………………………………………………………………. 1
B. The Fourth Amendment at its framing: the need
for particularity …………………………………………………………… 2
C. Updating the Fourth Amendment: new
technology, new interpretations, keeping
faith with privacy………………………………………………………… 5
D. The need for particularity and why it wasn’t met in
Ulbricht’s case ……………………………………………………………. 9
E. What must be done in general …………………………………… 12
F. What should have been done in Ulbricht’s case ………… 23

CONCLUSION …………………………………………………………………………………. 26
CERTIFICATE OF COMPLIANCE ……………………………………………….. 29
CERTIFICATE OF SERVICE …………………………………………………………. 30

ii

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TABLE OF AUTHORITIES
Sources

Page(s)

United States Supreme Court
Boyd v. United States,
116 U.S. 616 (1886) ………………………………………………………………………………. 3
Coolidge v. New Hampshire,
403 U.S. 443 (1971) …………………………………………………………………………20-21
Ex Parte Jackson,
96 U.S. 727 (1877) ………………………………………………………………………………… 6
Horton v. California,
496 U.S. 128 (1990) …………………………………………………………………………21-22
Katz v. United States,
389 U.S. 347 (1967) ………………………………………………………………………………. 7
Kentucky v. King,
563 U.S. 452 (2011) ………………………………………………………………………………. 4
Kyllo v. United States,
533 U.S. 27 (2001) …………………………………………………………………………… 7, 10
Marron v. United States,
275 U.S. 192 (1927) ……………………………………………………………………………. 4-5
Maryland v. Garrison,
480 U.S. 79 (1987) ………………………………………………………………………………. 11

Maryland v. King,
569 U.S. ___, 133 S.Ct. 1958 (2013) …………………………………………………….. 4
Olmstead v. United States,
277 U.S. 438 (1928) ……………………………………………………………………………. 5-6
Payton v. New York,
445 U.S. 573 (1980) ………………………………………………………………………………. 3

iii

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Riley v. California,
134 S.Ct. 2473 (2014)………………………………………………………………. 3, 8, 9, 12
Stanford v. Texas,
379 U.S. 476 (1965) ………………………………………………………………………………. 4
Steagald v. United States,
451 U.S. 204 (1981) ………………………………………………………………………………. 4
United States v. Jacobsen,
466 U.S. 109 (1984) ………………………………………………………………………………. 6
United States v. Jones,
132 S.Ct. 945 (2012) ………………………………………………………………………… 8, 10
United States v. Ramirez,
523 U.S. 65 (1998) ………………………………………………………………………………. 19
Second Circuit Court of Appeals
United States v. Galpin,
720 F.3d 436 (2d Cir. 2013) …………………………………………………………. 3, 9-10
United States v. Ganias,
755 F.3d 125 (2d Cir. 2014) ………………………………………………………………. 4, 8
United States v. Rodriguez,
775 F.3d 533 (2d Cir. 2014) ………………………………………………………………… 11
United States v. Rosa,
626 F.3d 56 (2d Cir. 2010) ………………………………………………………………. 5, 10
United States v. Voustianiouk,
685 F.3d 206 (2d Cir. 2012) ……………………………………………………………….. 4-5
United States Postal Service v. C.E.C. Servs.,
869 F.2d 184 (2d Cir. 1989) ………………………………………………………………… 13

iv

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Other Circuit Courts of Appeals
United States v. Angelos,
433 F.3d 738 (10th Cir. 2006) …………………………………………………………….. 19
United States v. Burgess,
576 F.3d 1078 (10th Cir. 2009) ……………………………………………………… 13, 19
United States v. Carey,
172 F.3d 1268 (10th Cir. 1999) ……………………………………………………….19-20
United States v. Christie,
717 F.3d 1156 (10th Cir. 2013) …………………………………………………………… 20
United States v. Comprehensive Drug Testing, Inc.,
621 F.3d 1162 (9th Cir. 2010) ……………………………………………………….. passim
United States v. Comprehensive Drug Testing, Inc.,
579 F.3d 989 (9th Cir. 2009)……………………………………………………………….. 20
United States v. Grimmett,
439 F.3d 1263 (10th Cir. 2006) ……………………………………………………….13-14
United States v. Maxwell,
285 F.3d 336 (4th Cir. 2002)……………………………………………………………….. 11
United States v. Otero,
563 F.3d 1127 (10th Cir. 2009) ……………………………………………………….. 5, 10
United States v. Riccardi,
405 F.3d 852 (10th Cir. 2005) …………………………………………………………….. 11
United States v. Tamura,
694 F.2d 591 (9th Cir. 1982)……………………………………………………………….. 15
Other Courts
Entick v. Carrington,
95 Eng. Rep. 807 (C.P. 1765) ……………………………………………………………….. 4

v

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In re Appeal of Application for Search Warrant,
71 A.3d 1158 (Vt. 2012) ………………………………………………………………… 13, 16
In the Matter of the Search of: 3817 W. West End, First Floor
Chicago, Illinois 60621,
321 F.Supp.2d 953 (N.D.Ill. 2004) ……………………………………………………… 13
Preventive Medicine Associates, Inc. v. Commonwealth,
465 Mass. 810 (2013) …………………………………………………………………….. 15, 23
State v. Bizewski,
2013 WL 1849282 (Conn. Super. Ct.) …………………………………………………. 14
United States v. Bonner,
2013 WL 3829404 (S.D. Cal.) ……………………………………………………………… 13
United States v. Falkowitz,
214 F.Supp.2d 365 (S.D.N.Y. 2002) ……………………………………………………. 13
United States v. Kim,
677 F.Supp.2d. 930 (S.D. Tex. 2009) ………………………………………………….. 21

Constitutional Provisions
U.S. CONST. amend. IV. ……………………………………………………………………… 12
Rules and Regulations
Fed. R. App. P. 26.1 ………………………………………………………………………………..i
Fed. R. App. P. 29(a) …………………………………………………………………………… ix
Fed. R. App. P. 29(c) ………………………………………………………………………. i, viii
Fed. R. App. P. 29(d) ………………………………………………………………………….. 29
Fed. R. App. P. 32(a) ………………………………………………………………………….. 29
Fed. R. App. P. 32(a)(7)(B)(iii) ……………………………………………………………. 29
Fed. R. App. P. 32(a)(7)(C) …………………………………………………………………. 29

vi

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Fed. R. Crim. P. 41(c) …………………………………………………………………………. 16
2d Cir. R. 29.1 ……………………………………………………………………………………. viii
Other Sources
Athul K. Acharya, Semantic Searches, 63 DUKE L.J. 393 (2013) …………….. 13
Office of Legal Educ. Exec. Office for United States Attorneys,
Searching and Seizing Computers and Obtaining Electronic
Evidence in Criminal Investigations, Dep’t of Justice: Computer
Crime and Intellectual Property Section, Criminal Division (2009),
http://www.justice.gov/criminal/cybercrime/docs/ssmanual2009.pdf
………………………………………………………………………………………………………..16-17
Orin S. Kerr, Searches and Seizures in a Digital World,
119 HARV. L. REV. 531 (2005) …………………………………………………………….. 20
Paul Ohm, Massive Hard Drives, General Warrants,
and the Power of Magistrate Judges, 97 VA. L. REV. IN BRIEF 1 (2011) ………. 23
Sam Tanenhaus & Jim Rutenberg, Rand Paul’s Mixed Inheritance,
NEW YORK TIMES, Jan. 25, 2014 ………………………………………………………… 11
10 WORKS OF JOHN ADAMS (C. Adams ed. 1856) ………………………………… 3

vii

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STATEMENT OF IDENTITY, INTEREST, AND AUTHORITY
Amicus the National Association of Criminal Defense Lawyers
(“NACDL”) is a nonprofit voluntary professional bar association that works on
behalf of criminal defense attorneys to ensure justice and due process for those
accused of crime or misconduct.1 NACDL was founded in 1958. It has a
nationwide membership of approximately 10,000 direct members in 28
countries, and 90 state, provincial, and local affiliate organizations totaling up
to 40,000 attorneys. NACDL’s members include private criminal defense
lawyers, public defenders, military defense counsel, law professors, and judges.
NACDL files numerous amicus briefs each year in the Supreme Court and other
courts seeking to provide amicus assistance in cases that present issues of broad
importance to criminal defendants, criminal defense lawyers, and the criminal
justice system as a whole. In particular, in furtherance of NACDL’s mission to
safeguard fundamental constitutional rights, the Association frequently appears
as amicus curiae in cases involving the Fourth Amendment and its state
analogues, speaking to the importance of balancing core constitutional search
and seizure protections with other societal interests.

1

Pursuant to Fed. R. App. P. 29(c)(5) and Rule 29.1 of this Court’s Local
Rules, amicus curiae certify that (1) this brief was authored entirely by counsel
for the NACDL, and not by counsel for any party, in whole or part; (2) no
party or counsel for any party contributed money to fund preparing or
submitting this brief; and (3) apart from the NACDL and its counsel, no other
person contributed money to fund preparing or submitting this brief.

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The NACDL files this brief in support of appellant Ross William
Ulbricht and urges the Court to reverse the District Court decision that denied
Ulbricht’s motion to suppress. The warrants that provided the authority for law
enforcement agents’ search and seizure of Ulbricht’s laptop computer and his
Gmail and Facebook accounts lacked a particularity statement as to the place to
be searched and things to be seized. They were, therefore, unconstitutional
general warrants.
The issue of particularity arising in this case has obvious ramifications
for Ulbricht. This case also reflects ongoing problems with warranting searches
of digital data in a way that promotes effective law enforcement while
protecting citizens’ privacy. While this balance has largely been established as
regards searches of physical spaces, such as mail sent through the United States
Postal Service, physical papers stored in someone’s home, medical records, or
books, courts, including this Court, offer very different and conflicting
approaches to balancing these interests in the digital context. The NACDL
therefore, also asks this Court to address those underlying issues through a
comprehensive articulation of core Fourth Amendment concepts, reinterpreted
for the digital age.
Pursuant to Fed. R. App. P. 29(a), amicus has sought and obtained
consent of all parties to file this brief.

ix

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ARGUMENT
I.

The warrants issued in this case lacked a limiting statement of
particularity and were therefore unconstitutional, violating the
original intent of the Fourth Amendment, extant historical and
contemporary jurisprudence, and this Court’s case law

A.

Introduction
Ulbricht argues, under his issue VI.A, that the District Court erred in

denying his motions to suppress evidence from his laptop and social media
accounts because the warrants authorizing those searches lacked any
particularity. (Blue Br. 2, 98-108). We argue that to satisfy the mandates of the
Fourth Amendment’s particularity requirement, courts must rethink how
magistrates draft and issue warrants. This includes paying special attention to
pre-search instructions as well as post-search reasonableness analyses. To that
end, we proceed in the following manner.
In section B, we discuss the original underpinnings of the Fourth
Amendment’s particularity requirement, which were greatly informed by the
evil of British general warrants and the concomitant need for limiting
statements of particularity.
In section C, we trace the development of Fourth Amendment
jurisprudence through eras of technological advancement, and show that in
each era, courts have been able to reinterpret the application of the Fourth
Amendment to meet new realities while remaining faithful to the Amendment’s

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core purpose: to protect individuals’ privacy against undirected and generalized
governmental rummaging.
In section D, we discuss the need for a careful assessment of
particularity statements in warrants to search digital data. We also discuss why
the particularity requirement was not satisfied in Ulbricht’s case.
In section E, we discuss the current law on warranted digital searches. In
this section, we discuss the issue of particularity and the use of both pre-search
instructions, championed by former Ninth Circuit Chief Judge Alex Kozinski,
see United States v. Comprehensive Drug Testing, Inc., 621 F.3d 1162 (9th Cir.
2010) [hereinafter CDT], and robust post-search reasonableness inquiries into
law enforcement agents’ warranted digital searches. Both pre-search
instructions and post-search reasonableness inquiries are necessary to ensure
the existence and effective operation of limiting statements of particularity.
In section F, we address the warrants that issued in Ulbricht’s case and
offer provisions that the magistrate should have included that would have
supplied the requisite particularity and still ensure effective law enforcement.
B.

The Fourth Amendment at its framing: the need for particularity
Fourth Amendment protections played an essential role in the founding

of the country, and were meant to provide refuge from the “general warrants”
deployed by British authorities during the colonial era, and which spurred the
American Revolution itself:

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Our cases have recognized that the Fourth Amendment was the
founding generation’s response to the reviled “general warrants”
and “writs of assistance” of the colonial era, which allowed British
officers to rummage through homes in an unrestrained search for
evidence of criminal activity. Opposition to such searches was in
fact one of the driving forces behind the Revolution itself. In
1761, the patriot James Otis delivered a speech in Boston
denouncing the use of writs of assistance. A young John Adams
was there, and he would later write that “[e]very man of a
crowded audience appeared to me to go away, as I did, ready to
take arms against writs of assistance.” 10 Works of John Adams
247-248 (C. Adams ed. 1856). According to Adams, Otis’s speech
was “the first scene of the first act of opposition to the arbitrary
claims of Great Britain. Then and there the child Independence
was born.” Id., at 248 (quoted in Boyd v. United States, 116 U.S.
616, 625 (1886)).
Riley v. California, 134 S.Ct. 2473, 2494 (2014); see also United States v.
Galpin, 720 F.3d 436, 445 (2d Cir. 2013) (the Fourth Amendment was framed
in opposition to the “indiscriminate searches and seizures conducted by the
British under the authority of general warrants.”) (quoting Payton v. New York,
445 U.S. 573, 583 (1980)) (internal quotes omitted).
The Supreme Court has long been concerned with general warrants and
the unbridled authority they give to law enforcement agents to engage in
boundless rummaging. As the Court noted in 1981,
[t]he general warrant specified only an offense . . . and left to the
discretion of the executing officials the decision as to which
persons should be arrested and which places should be searched.
Similarly, the writs of assistance used in the Colonies noted only
the object of the search . . . and thus left . . . officials completely
free to search any place where they believed such goods might be.
The central objectionable feature of both warrants was that they
provided no judicial check on the determination of the executing

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officials that the evidence available justified an intrusion into any
particular home.
Steagald v. United States, 451 U.S. 204, 220 (1981).
This Court expressed the same concern, noting that
General warrants were ones “not grounded upon a sworn oath of
a specific infraction by a particular individual, and thus not limited
in scope and application.” Maryland v. King, ___ U.S. ___, 133
S.Ct. 1958, 1980 (2013). The British Crown had long used these
questionable instruments to enter a political opponent’s home and
seize all his books and papers, hoping to find among them
evidence of criminal activity. See Stanford v. Texas, 379 U.S. 476,
482–83 (1965). The Framers abhorred this practice, believing that
“papers are often the dearest property a man can have” and that
permitting the Government to “sweep away all papers
whatsoever,” without any legal justification, “would destroy all the
comforts of society.” Entick v. Carrington, 95 Eng. Rep. 807,
817–18 (C.P. 1765).
United States v. Ganias, 755 F.3d 125, 134 (2d Cir. 2014).
No warrant, therefore, may issue “unless probable cause is properly
established and the scope of the authorized search is set out with particularity.”
Kentucky v. King, 563 U.S. 452, 459 (2011). This particularity requirement
“makes general searches . . . impossible and prevents the seizure of one thing
under a warrant describing another.” Marron v. United States, 275 U.S. 192,
196 (1927). The warrant must describe with particularity the place to be
searched and items to be seized, and the search and seizure must correspond to
those specific parameters, United States v. Voustianiouk, 685 F.3d 206, 211 (2d

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Cir. 2012), leaving “nothing . . . to the discretion of the officer executing the
warrant.” Marron, 275 U.S. at 196.
This Court has explicitly held that a warrant to search the contents of
laptops and storage devices, without a description of the exact items in which
the police were to search, violates the particularity requirement of the Fourth
Amendment. United States v. Rosa, 626 F.3d 56, 62 (2d Cir. 2010). Indeed, the
particularity requirement is “much more important” when a warrant permits a
search of a digital device, id. at 62 (quoting United States v. Otero, 563 F.3d
1127, 1132 (10th Cir. 2009)), and any government position “that the entire
contents of . . . computers and related storage media could be searched under
the terms of [a] warrant leads to the evisceration of the Fourth Amendment’s
requirement of an ex ante probable cause determination.” Id. at 62 n. 2.
C.

Updating the Fourth Amendment: new technology, new
interpretations, keeping faith with privacy
Fourth Amendment jurisprudence bends toward protecting individuals’

privacy rights by remaining faithful to the Framers’ concerns while responding
to new technologies — the application of the Fourth Amendment has changed,
but its concern with privacy, expressed in the requirement of a limiting
statement of particularity, has not and in the digital realm, should not.
Fourth Amendment jurisprudence originally entailed an exclusively
property law-oriented analysis based on concepts of trespass. See Olmstead v.

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United States, 277 U.S. 438 (1928). At a time when individuals’ papers and
effects were stored almost solely on their private property, the trespass
approach made sense because it ensured citizens’ privacy in light of
contemporary patterns of life and communication. New technologies inevitably
put strains on that approach, and courts, time after time, have successfully
adapted originalist Fourth Amendment jurisprudence to respond to those new
technologies.
The Pony Express, for example, began its service in 1860 and raised the
issue of mail privacy. This new communicative technology led to the innovative
holding in Ex Parte Jackson, which held that Fourth Amendment protections
extended to individuals’ missives, closed against inspection and sent through
the post. 96 U.S. 727, 733 (1877); see also United States v. Jacobsen, 466 U.S.
109, 113-14 (1984).
In Olmstead, the Supreme Court confronted the disruptive technology
of telephone service, holding that attaching a wire to a telephone line leaving
someone’s private residence was not a Fourth Amendment violation because
the Amendment could not be “extended and expanded to include telephone
wires, reaching to the whole world.” 277 U.S. at 465. Soon, however, the Court
recognized that new communicative technologies required it to untether its
jurisprudence from the once-universally applicable trespass approach.

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The Court therefore recognized that just as individuals’ communications
and private information had begun to extend beyond the confines of their
private property, these individuals’ Fourth Amendment protections had to
follow. Katz v. United States reconfigured Fourth Amendment jurisprudence
to focus not on trespass theory, but on a person’s expectation of privacy. 389
U.S. 347, 360-61 (1967) (Harlan, J., concurring). While Katz entailed a new
application of the Fourth Amendment, it fell directly in line with the Framers’
desire to protect people’s privacy, wherever that privacy was expressed.
Courts since Katz have been remarkably effective in confronting
originalist Fourth Amendment principles in light of fast-changing technology.
In Kyllo v. United States, the Supreme Court considered the constitutionality
of an officer’s use of an infrared heat detection device to virtually peer into
someone’s home — even though the device detected only heat emanating from
the home. 533 U.S. 27 (2001). The Court rejected a formalistic reading of
jurisprudence in favor of protecting individuals against the intrusiveness of new
surveillance technology:
We rejected such a mechanical interpretation of the Fourth
Amendment in Katz, where the eavesdropping device picked up
only sound waves that reached the exterior of the phone booth.
Reversing that approach would leave the homeowner at the mercy
of advancing technology — including imaging technology that
could discern all human activity in the home. While the
technology used in the present case was relatively crude, the rule
we adopt must take account of more sophisticated systems that
are already in use or in development.

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Id. at 35-36.
In United States v. Jones, the Court recognized that a formalistic
interpretation of the plain view doctrine had to give way to a new jurisprudence
in light of GPS tracking. In that case, the Court held that tracking a driver for
28 days constituted a search, even though the driver was tracked only while on
public streets. 132 S.Ct. 945 (2012).
And in Riley v. California, the Court held that during a search incident to
arrest, officers are permitted to search the contents of a cell phone only if they
obtain a warrant, 134 S.Ct. 2473, because cell phones today “place vast
quantities of personal information literally in the hands of individuals.” Id. at
2485. Thus, Fourth Amendment jurisprudence in the “context of physical
objects” has little “force with respect to digital content on cell phones.” Id. at
2484. The Court clarified that its holding applies to computers as well as cell
phones: “The term ‘cell phone’ is itself misleading shorthand; many of these
devices are in fact minicomputers . . . . One of the most notable distinguishing
features of modern cell phones is their immense storage capacity.” Id. at 2489.
This Court recognized the need for a new application of the Fourth
Amendment in Ganias, remarking that “[a]pplying 18th Century notions about
searches and seizures to modern technology . . . is easier said than done, as we
are asked to measure Government actions taken in the ‘computer age’ against

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Fourth Amendment frameworks crafted long before this technology existed.”
755 F.3d at 133 (footnote omitted). Thus, this Court’s “challenge is to adapt
traditional Fourth Amendment concepts to the Government’s modern, more
sophisticated investigative tools.” Id. at 134.
Fourth Amendment jurisprudence, indeed, must meet privacy demands
when the Government asks a magistrate judge for a warrant to search a digital
device or, essentially, the entirety of a target’s life. See Riley, 134 S.Ct. at 2490
(computers become “a digital record of nearly every aspect of [users’] lives —
from the mundane to the intimate.”).
D.

The need for particularity and why it wasn’t met in Ulbricht’s case
“[T]he computer hard drive [is] akin to a residence in terms of the scope

and quantity of private information it may contain.” Galpin, 720 F.3d at 446.
Where, therefore, “the property to be searched is a computer hard drive, the
particularity requirement assumes even greater importance.” Id. The use of
traditional, obsolete particularity statements in the digital context is fraught:
The potential for privacy violations occasioned by an unbridled,
exploratory search of a hard drive is enormous. This threat is
compounded by the nature of digital storage. Where a warrant
authorizes the search of a residence, the physical dimensions of
the evidence sought will naturally impose limitations on where an
officer may pry: an officer could not properly look for a stolen
flat-screen television by rummaging through the suspect’s
medicine cabinet, nor search for false tax documents by viewing
the suspect’s home video collection. Such limitations are largely
absent in the digital realm, where the size or other outwardly
visible characteristics of a file may disclose nothing about its

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content.
Id. at 447 (emphasis added). The Tenth Circuit echoed this sentiment:
The modern development of the personal computer and its
ability to store and intermingle a huge array of one’s personal
papers in a single place increases law enforcement’s ability
to conduct a wide-ranging search into a person’s private
affairs, and accordingly makes the particularity requirement
that much more important.
Otero, 563 F.3d at 1132 (cited favorably in Rosa, 626 F.3d at 61-62).
Accordingly, this Court mandates “a heightened sensitivity to the
particularity requirement in the context of digital searches” and, just as in Kyllo
and Jones, has expressed doubt as to the availability of the plain view exception
in the case of digital searches. Galpin, 720 F.3d at 447, 451.
Stating particularity, therefore, cannot be business as usual when it
comes to issuing warrants to search digital data. This Court knows that, but the
magistrate and the District Court in the instant case did not.
The District Court rejected Ulbricht’s particularity claim, countenancing
the government’s seizure of “the entirety of [Ulbricht’s] laptop and data on the
hard drive of that laptop . . . , along with the entirety of the accounts.” (District
Court Docket Entry No. 89, at 29).
The District Court gave Ulbricht’s argument short shrift. But the
warrants permitted a search for virtually anything and everything, including
“any communications or writings by Ulbricht, which may reflect . . .

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political/economic views associated with ‘Dread Pirate Roberts’ (e.g., views
associated with the Mises Institute”2; “any evidence concerning Ulbricht’s
travel or patterns of movement”; “any other evidence” implicating Ulbricht in
the subject crimes; and “[a]ny evidence concerning [Ulbricht] relevant to the
investigation of the SUBJECT OFFENSES, including but not limited to . . .
any communications or writings by ULBRICHT; . . . any evidence concerning
ULBRICHT’S travel or patterns of movement.” (Blue Br. 99).
Since “any” means “all,” United States v. Rodriguez, 775 F.3d 533, 537
(2d Cir. 2014) (quoting United States v. Maxwell, 285 F.3d 336, 341 (4th Cir.
2002)), these warrants permitted officers literally to search and seize all of
Ulbricht’s communications, writings, evidence of his movements and travels,
and all evidence that officers executing the search, in their discretion, deemed
relevant. The Tenth Circuit has, appropriately, not countenanced warrants that
permit officers to search for “anything,” because such warrants authorize
precisely the kind of “wide-ranging exploratory searches that the Framers
intended to prohibit.” United States v. Riccardi, 405 F.3d 852, 862 (10th Cir.
2005) (quoting Maryland v. Garrison, 480 U.S. 79, 84 (1987)).

2

The Mises Institute refers to itself as the center of the “Austrian Economics
Movement,” https://mises.org/about-mises, and is a libertarian organization
headquartered in Alabama. It was started with money raised by Senator Ron
Paul. Sam Tanenhaus & Jim Rutenberg, Rand Paul’s Mixed Inheritance, NEW
YORK TIMES, Jan. 25, 2014.

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The District Court was profoundly mistaken in concluding that these
warrants provided sufficient particularity to guide the officers who were tasked
with executing them. It heralded its blithe dismissal of Ulbricht’s claim by
proclaiming that because the warrant “identified the laptop and the accounts by
name,” everything in the computer and accounts could be seized. (District Court
Docket Entry No. 89, at 29). This is not the stuff of particularity statements,
but is that of warrants that would authorize what John Adams, James Otis, and
certainly the Riley Court would refer to as “rummag[ing] through homes in an
unrestrained search.” Riley, 134 S.Ct. at 2494.
E.

What must be done in general
As this Court has made clear, formalistic commitment to outdated forms

of particularity statements is not always appropriate to digital search warrants.
More is needed to adapt Fourth Amendment jurisprudence to modern
technology.
The starting point for this inquiry must be an acknowledgement that
warranted digital searches present officers with an unprecedented amount of
digital “papers[ ] and effects,” as the Framers would have put it. U.S. CONST.
amend. IV. The vast majority of these papers and effects will not constitute
evidence of criminality, and most will pertain to private issues such as medical
care, romantic relationships, political views, and so forth. The particularity

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requirement cannot be read to permit a magistrate to authorize the search and
seizure of all of these papers and effects.
To be sure, courts have, on occasion, permitted the bulk seizure of
papers and effects that include both materials that are indicative of crime and
those that are not. They permit such searches, however, only where there is
probable cause to believe that criminal activity permeates a business subject to
a search warrant, United States Postal Service v. C.E.C. Servs., 869 F.2d 184,
187 (2d Cir. 1989), and where the permission is based on the impossibility of
making a particularity statement that adequately separates potentially criminal
evidence from benign materials. United States v. Falkowitz, 214 F.Supp.2d 365,
388 (S.D.N.Y. 2002). Fortunately, in the digital context courts have a number
of tools at their disposal to ensure that officers executing warrants have a clear
mandate to perform only a limited, particularized search.
Magistrates have increasingly included pre-search instructions in digital
device warrants. CDT, 621 F.3d at 1168; United States v. Bonner, 2013 WL
3829404, at *19 (S.D. Cal.); In the Matter of the Search of: 3817 W. West End,
First Floor Chicago, Illinois 60621, 321 F.Supp.2d 953, 957 (N.D.Ill. 2004); In
re Appeal of Application for Search Warrant, 71 A.3d 1158 (Vt. 2012); Athul
K. Acharya, Semantic Searches, 63 DUKE L.J. 393, 409 (2013). Other courts favor
the traditional post-search reasonableness analysis. United States v. Burgess,
576 F.3d 1078, 1094 (10th Cir. 2009); United States v. Grimmett, 439 F.3d

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1263, 1270 (10th Cir. 2006); State v. Bizewski, 2013 WL 1849282, at *13 (Conn.
Super. Ct.). We argue that pre-search instructions, judiciously applied, play a
vital role in both establishing a particularity statement in a warrant and enabling
a meaningful post-search reasonableness inquiry.
As to pre-search instructions, former Ninth Circuit Chief Judge Alex
Kozinski’s concurring opinion in CDT is instructive. In that opinion, Chief
Judge Kozinski advocated for magistrates’ use of five pre-search instructions.
In CDT, the Ninth Circuit considered the execution of a warrant to search the
digital records of Comprehensive Drug Testing, a facility that administered
tests on hundreds of major league baseball players for steroid use. 621 F.3d at
1166. Although the warrant was based on probable cause to believe that only
ten players had broken the law, “the government seized and promptly reviewed
the drug testing records for hundreds of players in Major League Baseball (and
a great many other people).” Id.
To justify its broad seizure, the government noted in its search warrant
application the “generic hazards of retrieving data that are stored
electronically.” CDT, 621 F.3d at 1168. The magistrate judge therefore
permitted the government to seize virtually all computer equipment found
along with any data storage devices and related materials. Id. The magistrate
did, however, require that the government employ a taint team, or a third party
— not the person or entity in possession of the seized evidence and not the

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agents who performed the search or members of the investigatory or
prosecution team — to separate innocuous seized data from incriminating
evidence, pursuant to United States v. Tamura, 694 F.2d 591 (9th Cir. 1982).
CDT, 621 F.3d at 1168; see also Preventive Medicine Associates, Inc. v.
Commonwealth, 465 Mass. 810, 829 (2013).
CDT is different than Ulbricht’s case in one regard: in CDT, the
Government admitted that its agents’ intent was to take all of the digital
evidence “and later on briefly peruse it to see if there was anything above and
beyond that which was authorized for seizure in the initial warrant,” CDT, 621
F.3d at 1171, whereas in Ulbricht’s case the officers could not go beyond the
warrants’ particularity limits because there were no limits.
Judge Kozinski’s response was to offer five pre-search instructions that
magistrates could include in warrants to ensure particularity:
1. Magistrate judges should insist that the government waive
reliance upon the plain view doctrine in digital evidence cases.
2. Segregation and redaction of electronic data must be done
either by specialized personnel or an independent third party. If
the segregation is to be done by government computer personnel,
the government must agree in the warrant application that the
computer personnel will not disclose to the investigators any
information other than that which is the target of the warrant.
3. Warrants and subpoenas must disclose the actual risks of
destruction of information as well as prior efforts to seize that
information in other judicial fora.
4. The government’s search protocol must be designed to uncover

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only the information for which it has probable cause, and only
that information may be examined by the case agents.
5. The government must destroy or, if the recipient may lawfully
possess it, return non-responsive data, keeping the issuing
magistrate informed about when it has done so and what it has
kept.
Id. at 1180 (Kozinski, CJ., concurring) (citations omitted).
The Vermont Supreme Court has discussed why appropriate use of
these pre-search instructions is vital, observing:
In the digital universe, particular information is not accessed
through corridors and drawers, but through commands and
queries. As a result, in many cases, the only feasible way to specify
a particular ‘region’ of the computer will be by specifying how to
search. We view such ex ante specification as an acceptable way to
determine particularity.
In re Appeal of Application for Search Warrant, 71 A.3d at 1171.
In the digital context, particularity may require use of some or all of
these pre-search instructions. These instructions should be used to ensure that
warrants do what they have always done: prohibit officers from searching
locations they have no probable cause to search. Such instructions ensure
particularity by identifying whether the hardware itself is evidence of a crime,
i.e. contains contraband or is contraband, or is an instrumentality of a crime, or
if the hardware simply stores evidence of a crime. See Fed. R. Crim. P. 41(c);
see also Office of Legal Educ. Exec. Office for United States Attorneys,
Searching and Seizing Computers and Obtaining Electronic Evidence in Criminal

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Investigations, Dep’t of Justice: Computer Crime and Intellectual Property
Section, Criminal Division, 63 (2009),
http://www.justice.gov/criminal/cybercrime/docs/ssmanual2009.pdf. The
warrant should permit the search and seizure of relevant computer files rather
than the digital media itself. It should also identify records that relate to the
particular crime for which officers have probable cause to search, including
specific categories of or types of records to be found. This type of information
can be discerned by, for example, the identity of the target of the search, the
time frame of the crime being investigated, or the actual crime itself, like child
pornography. Id. at 72-73.
The particularity requirements for a warrant to search for digital
evidence should be detailed enough to clearly and unambiguously inform law
enforcement as to what is included and what is not included within the scope
of the approved search. To accomplish that objective, the articulation of the
specific target of the search must utilize the narrowest particulars necessary to
discriminate between what is and is not to be searched.
Take, for example, a search of a personal laptop computer to obtain
evidence of a physician’s alleged illegal distribution of pain medications. The
warrant first must specifically identify the physical address where the computer
is to be found and the location on the premises where it is located. The warrant
must also specify the type of computer to be searched (in this case a specific

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make of laptop), and then specify the type and content of digital files to be
searched. Such file types and content would be limited in this example to text
documents in which search queries reveal the presence of the doctor’s DEA
number, names and addresses of patients referenced in the allegedly illegal
prescriptions, and emails to and from those patients. Without more supporting
investigative information, the image files on the computer, other emails, and
personal documents not specific to the doctor’s prescription authority would
be excluded from the warrant to search. Such particularities carve out the scope
of the warranted search from the general population of files stored on the
laptop.
Search protocols should be outlined for how the government plans to
conduct onsite and offsite searches of digital devices, and can be suggested by
government agents when they apply for warrants. Agents should explain how
these protocols will keep their search within the bounds of the warrant. Such
protocols may include the use of a taint team, restrictions on information
sharing between the taint team and law enforcement investigators and
prosecutors, obtaining a warrant when evidence of a separate crime is
legitimately within plain view, the use of search terms, and the use of forensic
software.
Pre-search instructions are vital to meaningful post-search
reasonableness inquiries that every magistrate must perform. After all, with no

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pre-search instructions in the digital context, officers will be authorized by the
warrant to perform a virtual basement-to-attic sweep of every nook and cranny
of a computer. If their search is not bounded by pre-search instructions, then
nothing is unreasonable. This certainly cannot be the judiciary’s (non-)response
to new technology.
The Tenth Circuit recognized the inextricable connection between presearch instructions and post-search reasonableness, writing that the provision
of and adherence to the former will contribute greatly to a reasonableness
analysis favorable to the government:
This isn’t to say the Fourth Amendment has nothing to say on how
a computer search should proceed. Even putting aside for the
moment the question what limitations the Fourth Amendment’s
particularity requirement should or should not impose on the
government ex ante, the Amendment’s protection against
“unreasonable” searches surely allows courts to assess the
propriety of the government’s search methods (the how) ex post in
light of the specific circumstances of each case. See, e.g., United
States v. Ramirez, 523 U.S. 65, 71 (1998) (“The general
touchstone of reasonableness . . . governs the method of
execution of the warrant.”); United States v. Angelos, 433 F.3d
738, 746 (10th Cir. 2006). So even if courts do not specify
particular search protocols up front in the warrant application
process, they retain the flexibility to assess the reasonableness of
the search protocols the government actually employed in its
search after the fact, when the case comes to court, and in light of
the totality of the circumstances. Unlike an ex ante warrant
application process in which the government usually appears
alone before generalist judges who are not steeped in the art of
computer forensics, this ex post review comes with the benefit,
too, of the adversarial process where evidence and experts from
both sides can be entertained and examined. See Burgess, 576
F.3d at 1094; United States v. Carey, 172 F.3d 1268, 1275-76

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(10th Cir. 1999); Orin S. Kerr, Searches and Seizures in a
Digital World, 119 HARV. L. REV. 531, 574–75 (2005).
United States v. Christie, 717 F.3d 1156, 1166-67 (10th Cir. 2013).
To be sure, case-specific realities will drive which pre-search instructions
a magistrate must include to ensure both particularity and the magistrate’s
ability to perform a meaningful post-search reasonableness analysis. Although
they were originally fashioned as mandates, United States v. Comprehensive
Drug Testing, Inc., 579 F.3d 989, 1006-07 (9th Cir. 2009), Chief Judge
Kozinski’s pre-search instructions became admonitory guidelines that
magistrates should consider and impose as necessary. CDT, 621 F.3d at 1180.
In addition to magistrates’ role in authorizing appropriately limited searches by
use of pre-search instructions, the Government should proactively self-impose
them in warrant applications wherever possible.
In addition to imposing some or all of Chief Judge Kozinski’s five presearch instructions and performing robust traditional post-search
reasonableness inquiries, magistrates might consider a second limitation. They
could require officers to foreswear reliance on the plain view doctrine. This is
important because, surprising at it may seem, the Government’s admission in
CDT that it fully intended to seize evidence beyond the scope of its warrant is
grounded in law.
In Coolidge v. New Hampshire, the Supreme Court first explicitly

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established that to rely on the plain view doctrine to seize evidence that was
beyond the scope of a warrant, agents must have arrived at the evidence
inadvertently. 403 U.S. 443, 469-70 (1971). In turn, where “discovery is
anticipated,” agents could not rely on plain view. Id. at 470.
Nearly 20 years later, however, in Horton v. California, the Court
rejected the inadvertence requirement, 496 U.S. 128, 137 (1990), mandating
only that agents come to evidence in plain view lawfully — that is, within the
scope of the warrant — and that the incriminating character of the evidence be
“immediately apparent.” Horton, 496 U.S. at 136. This means that during a
warranted search for evidence of credit card fraud, if agents come across a
folder labeled “kiddiepornpics,” agents may nevertheless perform a detailed
search of the contents of that folder, even if they intend to find evidence of
child pornography and not credit card fraud. See United States v. Kim, 677
F.Supp.2d. 930, 945, 949-50 (S.D. Tex. 2009). This is so because of the general
non-discernibility of digital evidence; a file labeled “kiddiepornpics” could
technically contain evidence of credit card fraud. It does not matter that most
people would think it unreasonable to believe that evidence of credit card fraud
would be hidden in such a folder. In the digital context, the Government would
argue, this means that once a warrant to search digital devices issues, agents
may search the entirety of the devices, even if they are attempting and
expecting to find evidence of any crime (or even any unpopular, but legal,

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conduct), whether or not it is set forth in the warrant. This is the very
definition of unbounded rummaging that the Fourth Amendment’s
particularity requirement abhors.
The way to avoid this unbounded rummaging is two-fold. First,
magistrates could require agents to foreswear reliance on plain view, meaning
that if they have a warrant to search for evidence of crime A, they may perform
a search only for evidence of crime A; if they believe they may capture evidence
of crime B, they may not use the technical authorization of the warrant and
Horton to go beyond the search for evidence of crime A; to do so would
constitute an unreasonable, extrajudicial fishing expedition.
Second, foreswearing reliance on plain view does not mean that agents
will be unreasonably hobbled in their good-faith efforts to uncover evidence of
crime A. Agents may certainly search for evidence of crime A in a reasonable
manner, as bounded by the magistrate’s pre-search instructions, and need not
fear losing evidence of crime B should they inadvertently come across it. If they
do unexpectedly uncover evidence of crime B, however, they should
immediately stop the search, freeze the scene, and seek a warrant to search for
evidence of crime B (their warrant to search for evidence of crime A would, of
course, still be in effect).
Courts have suggested that this two-step process is reasonable and may
be necessary to ensure particularity in digital warrants and searches. The

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Massachusetts Supreme Judicial Court expressed its concern that
a cursory review of every e-mail undermines the particularity
requirement of the Fourth Amendment and art. 14 [of the U.S.
Constitution], particularly where . . . the cursory review is joined
with the plain view doctrine to enable the Commonwealth to use
against the defendants inculpatory evidence with respect to the
pending indictments that it finds in the emails, even though such
evidence may not actually fit within the scope of the search
warrants obtained.
Preventive Medicine Associates, Inc., 465 Mass. at 831-32. Similarly, Fourth
Amendment scholar Orin Kerr has argued that “computer technologies may
allow warrants that are particular on their face to become general warrants in
practice.” Searches and Seizures in a Digital World, 119 HARV. L. REV. 531, 565
(2005). And Paul Ohm has observed that “[c]omputer search warrants are the
closest things to general warrants we have confronted in the history of the
Republic.” Massive Hard Drives, General Warrants, and the Power of Magistrate Judges,
97 VA. L. REV. IN BRIEF 1, 11 (2011).
F. What should have been done in Ulbricht’s case
Ulbricht does not, of course, bear any burden to show how the magistrate
might have drafted a warrant that included an adequate particularity statement;
he only needs to show that the warrant lacked such a statement. Nevertheless,
how the magistrate might have drafted an adequate particularity statement is
not difficult to show, and doing so illustrates why, in the instant case, the
warrants provided no particularity. There are at least five particularized

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alternatives to the District Court’s warrant language that demonstrate
practicable approaches to ensuring effective law enforcement and satisfaction
of the constitutional necessity of particularity.
First, the District Court indicated that Ulbricht’s computer was “likely to
contain evidence concerning ULBRICHT relevant to the investigation of the
SUBJECT OFFENSES, including evidence relevant to corroborating the
identification of ULBRICHT as the Silk Road user ‘Dread Pirate Roberts.’”
(Blue Br. 99). Presumably, prior to seeking the warrants at issue, law
enforcement agents had amassed evidence that a certain party was engaged in
online criminal conduct as the Dread Pirate Roberts. Agents would, therefore,
be aware of the particular screen name(s) or online handle(s) that this person
used when operating as the Dread Pirate Roberts. He or she could have gone
by “Dread Pirate Roberts,” “DPR,” “Dread,” and so forth. Any online handle
used by this person would be inevitably stored in that person’s computer, and
subject to a word or term search. The magistrate, therefore, could have
authorized a very broad, but particularized search for documents, texts,
Internet activity, and anything else containing “Dread Pirate Roberts,” “DPR,”
“Dread,” “Pirate,” “Roberts,” and any other relevant word or combination of
words.
Second, the magistrate authorized a search for “any communications or
writings by Ulbricht, which may reflect linguistic patterns or idiosyncrasies

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associated with ‘Dread Pirate Roberts’[] or political/economic views associated
with ‘Dread Pirate Roberts.’” (Blue Br. 99). Again, we presume that agents were
familiar with these linguistic patterns and idiosyncrasies prior to seeking the
search warrants, for if they had not been, then this warrant truly would
authorize a fishing expedition without any basis in probable cause. Since agents
were familiar with these patterns and idiosyncrasies, they would have been able
to identify the unique words, phrases, spellings, and so forth associated with
Dread Pirate Roberts. These words, phrases, and spellings are eminently
susceptible to key word and phrase searching on a computer. The magistrate
could have permitted a search only for these idiosyncrasies.
Third, the magistrate authorized a search for “any evidence concerning
Ulbricht’s travel or patterns of movement, to allow comparison with patterns
of online activity of ‘Dread Pirate Roberts’ and any information known about
his location at particular times.” (Blue Br. 99). Here again, agents must have
been aware of the dates that the online Dread Pirate Roberts was travelling or
located in certain places that they wanted to compare against evidence found
on Ulbricht’s computer. The magistrate could have authorized a search only for
files and computer activity associated with these dates and locations. This
would have been easy to do: date-limited searches of hard drives is a routine
process, and if agents were aware of the online Dread Pirate Roberts’ location
in the physical world, it would be by tracing IP addresses, also readily

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searchable on Ulbricht’s computer.
Fourth, the magistrate authorized a search for “any other evidence
implicating ULBRICHT in the SUBJECT OFFENSES.” (Blue Br. 99). This
catch-all global authorization is not tied to any evidence agents might have
presented to the magistrate, and thus there is absolutely no probable cause
supporting it. This authorization should simply not have been included.
Fifth, the magistrate did not, but could have required the use of a neutral
taint team to separate the innocuous content of Ulbricht’s laptop and social
media accounts from any incriminating matter that might have been discovered
therein.
CONCLUSION
Digital devices store unprecedented amounts of data, including text
documents, financial records, images, videos, e-books, web search histories,
and other data that touch on virtually every aspect of a user’s life. Without
some cursory inspection, each file can appear to be indistinguishable from any
other file. Simply opening the cover of a laptop will not reveal a box of family
photos next to a medical bill next to an illegal narcotics ledger. The massive
amount of sometimes-indistinguishable data presents new Fourth Amendment
challenges to magistrates who endeavor to provide constitutionally-required
particularity statements in the warrants they issue.

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Just as courts have responded to disruptive technology in the past,
courts are now generating new types of particularity statements that ensure
individuals’ privacy and do not hobble law enforcement efforts. Pre-search
instructions and robust post-search reasonableness inquiries connected to those
instructions are the loci of courts’ response.
This Court should adopt that framework in reviewing the adequacy of
digital search warrants by issuing a detailed opinion discussing its view of presearch instructions and requiring lower courts to engage in robust post-search
reasonableness inquiries. This Court should also acknowledge the inextricable
link between imposition of pre-search instructions and the ability to perform
meaningful post-search reasonableness inquiries.
Ulbricht’s specific case is much simpler, because the warrants to search
his digital device and accounts lacked any particularity and the District Court
judge engaged only in a blithe dismissal of his claims, not a genuine post-search
reasonableness analysis. This Court should, therefore, reverse the District
Court’s denial of his motion to suppress, vacate his conviction, and remand to
District Court for a new trial consistent with this Court’s opinion.

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Dated: January 19, 2016
Grand Forks, North Dakota
Respectfully submitted,

Steven R. Morrison
Steven R. Morrison
University of North Dakota
School of Law
1526 Robertson Court
Grand Forks, ND 58201
(617) 749-7817
Joel B. Rudin
Law Offices of Joel B. Rudin, P.C.
600 Fifth Avenue, 10th Floor
New York, NY 10020
(212) 752-7600
Attorneys for Amicus Curiae National
Association of Criminal Defense Lawyers

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CERTIFICATE OF COMPLIANCE
Pursuant to Fed. R. App. P. 32(a)(7)(C), I hereby certify that this brief
complies with the type-volume limitations of Fed. R. App. P. 29(d) and 32(a)
because it was produced using Garamond typeface in 14-point font and
contains 6,895 words, excluding the parts of the brief exempted by Rule
32(a)(7)(B)(iii), according to the word processing system I utilized.
Dated: January 19, 2016
Grand Forks, North Dakota

Steven R. Morrison
Steven R. Morrison

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CERTIFICATE OF SERVICE
I hereby certify that on this date a copy of the foregoing was filed
electronically with the Court’s CM/ECF system. Notice of this filing will be
sent by email to all parties by operation of the Court’s electronic filing system.
Parties may access this filing through the Court’s CM/ECF system.
Dated: January 19, 2016
Grand Forks, North Dakota

Steven R. Morrison
Steven R. Morrison

30