Commonwealth v. Dorelas

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SJC-11793

COMMONWEALTH vs. DENIS DORELAS.

Suffolk. April 7, 2015. - January 14, 2016.

Present: Gants, C.J., Spina, Cordy, Botsford, Duffly, Lenk, &
Hines, JJ.

Constitutional Law, Search and seizure, Probable cause. Search
and Seizure, Warrant, Probable cause. Probable Cause.
Cellular Telephone.

Indictments found and returned in the Superior Court
Department on September 27, 2011.

A pretrial motion to suppress evidence was heard by Patrick
F. Brady, J.

An application for leave to prosecute an interlocutory
appeal was allowed by Botsford, J., in the Supreme Judicial
Court for the county of Suffolk, and the case was reported by
her to the Appeals Court. The Supreme Judicial Court granted an
application for direct appellate review.

Nancy A. Dolberg, Committee for Public Counsel Services,
for the defendant.
John P. Zanini, Assistant District Attorney, for the
Commonwealth.
Robert E. McDonnell, John Frank Weaver, Arcangelo S. Cella,
Matthew R. Segal, Jessie J. Rossman, & Mason Kortz, for American
Civil Liberties Union of Massachusetts, amicus curiae, submitted
a brief.
 2

CORDY, J. In this case we consider whether, where there

was probable cause for the issuance of a warrant to search an

Apple iPhone,1 the search and seizure of certain photograph files

conducted in reliance thereon was reasonable.

The warrant authorized a search of the defendant's iPhone

for evidence of communications that would link him and another

suspect to a shooting that occurred in the Hyde Park section of

Boston. The search tool used to extract data from the iPhone

was programmed to extract not only contact lists and text

messages (texts), but also photographs. Among the photographs

extracted and examined by the police were photographs depicting

the defendant holding a gun and dressed in the same color jacket

described by witnesses to the shooting.

We conclude that where there was probable cause that

evidence of communications relating to and linking the defendant

to the crimes under investigation would be found in the

electronic files on the iPhone, and because such communications

can be conveyed or stored in photographic form, a search of the

photograph files was reasonable. Finally, we conclude that the

1
An iPhone, which is manufactured by Apple Inc., is a type
of "smart" cellular telephone (smartphone) that, in addition to
making telephone calls, can transmit text messages (texts),
perform the functions of both a camera and a video recorder,
enable the operation of various applications, and connect to the
Internet.
 3

photographs in question were properly seized as evidence linking

the defendant to the crimes under investigation.

Background. On July 3, 2011, at approximately 7 P.M.,

Detective Richard Walker and other Boston police officers

responded to reports of a shooting at 74 Pierce Street in Hyde

Park. On arrival, the responding officers found Michael Lerouge

with gunshot wounds to his back. The police found a black

Glock, model 23, .40 caliber firearm in the middle of the

roadway between 73 and 74 Pierce Street. Witnesses told the

police that Lerouge and another person had shot at one another

and that Lerouge had discarded the firearm under a parked motor

vehicle, after which it slid further into the road. The police

were also informed that the other shooter, described as wearing

a green-colored shirt or jacket with writing on it, had run down

Pierce Street toward Walter Street, dropping a firearm in the

process. Witnesses stated that this man stopped, retrieved the

dropped firearm, and then continued to run in the direction of

86 Pierce Street. The defendant was subsequently found on the

left side of 86 Pierce Street, wearing a green jacket with

emblems and suffering from gunshot wounds to his left leg.

When the police found the defendant, he was with Jamal

Boucicault, who was subsequently interviewed at the police

station. Boucicault told the police that he was visiting the

defendant in an apartment at 86 Pierce Street when the defendant
 4

received a telephone call. The defendant began arguing with the

caller and subsequently left the apartment. A short time later,

Boucicault heard what sounded like gunshots and went outside to

find the defendant on the left side of the house at 86 Pierce

Street. The defendant handed Boucicault a gun and asked him to

hide it, and he then did so in the apartment at 86 Pierce

Street.

The defendant's brother, Bricknell Dorelas, also spoke with

the police after the incident. He stated that earlier in the

evening he had received a telephone call from the defendant, in

which the defendant stated that he "was receiving threatening

[tele]phone calls and threatening text messages on his

[tele]phone." Bricknell did not know the identity of the person

who was threatening the defendant. The police also spoke with a

cousin of the defendant, Ohuinel Normil, who said the defendant

"had been getting a lot of telephone threats because he owes

money to people." Normil did not know the identity of these

people.

The owner of 86 Pierce Street told the police that he

rented the rear apartment on the second floor of the building to

the defendant, and that the defendant was the apartment's sole

occupant. Thereafter, the police applied for, received, and
 5

executed a search warrant for the defendant's apartment.

Pursuant to that warrant, the police seized a gun and an iPhone.2

Based on the information above, Walker believed that the

defendant's iPhone contained information linking both the

defendant and Lerouge to the crimes of assault and battery by

means of a dangerous weapon (firearm) and assault with intent to

murder that were under investigation. Accordingly, he applied

for a warrant to search the iPhone. In his affidavit, which was

attached to his application for the warrant, Walker set out the

substance of the investigative interviews and concluded by

stating: "Based on the above facts . . . I have probable cause

to believe [the defendant's] cell phone contains valuable

information that will link the victim/suspect ([the defendant])

and suspect/victim (Lerouge) to the crime." Walker received and

executed a warrant to search the defendant's iPhone for the

following:

"Subscriber's name and telephone number, contact list,
address book, calendar, date book entries, group list,
speed dial list, phone configuration information and
settings, incoming and outgoing draft sent, deleted text
messages, saved, opened, unopened draft sent and deleted
electronic mail messages, mobile instant message chat logs
and contact information mobile Internet browser and saved

2
The defendant told the police that the iPhone belonged to
him. This statement was subsequently suppressed, but the motion
judge concluded that there remained "sufficient information" for
the magistrate to conclude that the iPhone belonged to the
defendant, as he was the sole occupant of the apartment on
Pierce Street in which the iPhone was found.
 6

and deleted photographs on an Apple iPhone, silver and
black, green soft rubber case. Additionally, information
from the networks and carriers such as subscribers
information, call history information, call history
containing use times and numbers dialed, called, received
and missed."3

Among other items, the search resulted in the discovery and

seizure of photographs of the defendant wearing a green jacket

and holding a gun.4 The date the photographs were taken, stored,

or received is not apparent in the record on the motion to

suppress, and the defendant does not claim that the photographs

were taken, stored, or received at times remote from the

shooting.

Procedural history. In September, 2011, the defendant was

charged by a Suffolk County grand jury with possession of a

firearm without a license, in violation of G. L. c. 269,

§ 10 (a); possession of ammunition without a firearm

3
The warrant is awkwardly written, conflating at least in
part the items to be searched for and the places to be searched.
We agree with the dissent that as written the warrant and the
warrant application are overly broad. But considered in
conjunction with the affidavit incorporated therein, a
commonsense reading shows that the warrant authorized a search
of various types of files for evidence of communications that
would link the defendant and another person to the shooting.
This is the reading that the motion judge appears to have given
the warrant.
4
The complete inventory return lists the following taken as
a result of the warrant: "Phone Examination Report Properties"
(which includes texts), "Phone Examination Report Index," "Phone
Contacts," "Phone Incoming Call List," "Phone Outgoing Call
List," "Phone Missed Call List," "Images," and "Video."
 7

identification card, in violation of G. L. c. 269, § 10 (h);

carrying a loaded firearm, in violation of G. L. c. 269,

§ 10 (n); and possession of a large capacity feeding device

without a license, in violation of G. L. c. 269, § 10 (m).5

The defendant filed a number of motions to suppress

evidence, only one of which is relevant on appeal. In March,

2013, he filed a motion to suppress the photographs6 obtained

from the search of his iPhone, which was denied after an

evidentiary hearing.7 In his arguments to the motion judge, the

defendant conceded that the search warrant affidavit provided

probable cause to search the iPhone for text messages and

photographs attached to text messages relevant to the shooting

under investigation, but that it was unreasonable to search the

5
Although the defendant was initially charged with offenses
related to the shooting, the Commonwealth's investigation
determined that the defendant acted in self-defense when he
allegedly fired a gun. The fact that subsequent investigation
by the police indicated that the defendant was acting in self-
defense in the shooting is irrelevant to the validity and scope
of the search.
6
The motion also sought to suppress video recordings
obtained during the search. The Commonwealth represented that
it would not be using any video recordings recovered from the
iPhone, and therefore the defendant has not made any arguments
relating to those recordings on appeal. We offer no opinion as
to whether video recordings were properly within the scope of
the search authorized by the warrant.
7
The only witness to testify at the evidentiary hearing was
Joseph Nicholls, a computer forensics examiner called by the
defense.
 8

photograph files on his iPhone for such evidence. The motion

judge held, in relevant part, that it was appropriate for the

police to search the files on the defendant's iPhone that

contained his photographs because the affidavit "furnished

probable cause to conduct an electronic search of [his] cell

phone" and because threats can be communicated by way of

photographs and stored in the iPhone's photograph file. The

defendant filed a timely notice of appeal. In July, 2013, a

single justice of this court allowed the defendant's petition

for leave to file an interlocutory appeal and ordered the appeal

to be filed in the Appeals Court. In December, 2014, this court

granted the defendant's application for direct appellate review.

Discussion. On appeal, the defendant argues that the

motion to suppress photographs was wrongly denied, as there was

not probable cause to search his iPhone's photograph file for

evidence linking him to Lerouge or the shooting.8

When considering the sufficiency of a search warrant

application, our review "begins and ends with the four corners

of the affidavit" (quotation and citations omitted).9

8
The defendant also argues on appeal that the warrant
lacked particularity as to the items to be seized and the places
to be searched. Where these arguments were not made in the
trial court, we do not consider them here.
9
General Laws c. 276, § 2B, requires that all of the
information establishing probable cause be in the affidavit.
 9

Commonwealth v. Cavitt, 460 Mass. 617, 626 (2011). "In

determining whether an affidavit justifies a finding of probable

cause, the affidavit is considered as a whole and in a

commonsense and realistic fashion . . . ." Id. The affidavit

should not be "parsed, severed, and subjected to hypercritical

analysis" (quotation and citation omitted). Commonwealth v.

Donahue, 430 Mass. 710, 712 (2000). "All reasonable inferences

which may be drawn from the information in the affidavit may

also be considered as to whether probable cause has been

established." Id. Importantly, "[w]e give considerable

deference to a magistrate's determination of probable cause."

Commonwealth v. McDermott, 448 Mass. 750, 767, cert. denied, 552

U.S. 910 (2007).

The Fourth Amendment to the United States Constitution and

art. 14 of the Massachusetts Declaration of Rights "both require

a magistrate to determine that probable cause exists before

issuing a search warrant" (quotation and citation omitted).

Cavitt, 460 Mass. at 626. "[P]robable cause requires a

substantial basis . . . for concluding that the items sought are

related to the criminal activity under investigation, and that

they reasonably may be expected to be located in the place to be

searched at the time the search warrant issues" (quotations and

citations omitted). Commonwealth v. Kaupp, 453 Mass. 102, 110

(2009). See McDermott, 448 Mass. at 768 (probable cause to
 10

search residence where "reasonably likely that the items

specified in the affidavit could be found there" [quotation and

citations omitted]).10

In the physical world, police need not particularize a

warrant application to search a property beyond providing a

specific address, in part because it would be unrealistic to

expect them to be equipped, beforehand, to identify which

specific room, closet, drawer, or container within a home will

contain the objects of their search. Rather, "[a] lawful search

of fixed premises generally extends to the entire area in which

the object of the search may be found" (emphasis added). See

United States v. Ross, 456 U.S. 798, 820 (1982).

However, in the virtual world, it is not enough to simply

permit a search to extend anywhere the targeted electronic

objects possibly could be found, as data possibly could be found

anywhere within an electronic device. Thus, what might have

10
General Laws c. 276, § 1, provides that a court or
justice is authorized to issue a warrant "if satisfied that
there is probable cause" for the complainant's sworn belief
"that any of the property or articles hereinafter named are
concealed in a house, place, vessel or vehicle." The warrant
must also identify the property and name or describe "the person
or place to be searched." Id.
 11

been an appropriate limitation in the physical world becomes a

limitation without consequence in the virtual one.11

Nevertheless, much like a home, such devices can still

appropriately be searched when there is probable cause to

believe they contain particularized evidence. See McDermott,

448 Mass. at 770-772. However, given the properties that render

an iPhone distinct from the closed containers regularly seen in

the physical world, a search of its many files must be done with

special care and satisfy a more narrow and demanding standard.

See Hawkins v. State, 290 Ga. 785, 786-787 (2012) (cellular

telephone is "roughly analogous" to container, but large volume

11
We recognize that individuals have significant privacy
interests at stake in their iPhones and that the probable cause
requirement of search warrants under both the Fourth Amendment
to the United States Constitution and art. 14 of the
Massachusetts Declaration of Rights serves to protect these
interests. In its recent landmark decision of Riley v.
California, 134 S. Ct. 2473, 2488-2491 (2014), the United States
Supreme Court explained how the privacy interests implicated in
smartphone searches "dwarf" those in cases in which a limited
information is contained in a finite space, given the volume,
variety, and sensitivity of the information either stored in a
smartphone or stored remotely and accessed through a smartphone.
Calling a smartphone a "phone" is a "misleading shorthand; many
of these devices are in fact minicomputers that also happen to
have the capacity to be used as a telephone." Id. at 2489.
"They could just as easily be called cameras, video players,
rolodexes, calendars, tape recorders, libraries, diaries,
albums, televisions, maps, or newspapers." Id. See
Commonwealth v. Phifer, 463 Mass. 790, 797 (2012). An iPhone
has the same operating system as an Apple computer. In 2014,
the storage capacities of iPhones ranged from sixteen to sixty-
four gigabytes. See Riley, supra at 2489. Such devices can
hold hundreds of thousands of files, including millions of pages
of text and thousands of photographs. See id.
 12

of information contained in cellular telephone "has substantial

import as to the scope of the permitted search," which must be

done with "great care and caution"). "Officers must be clear as

to what it is they are seeking on the [iPhone] and conduct the

search in a way that avoids searching files of types not

identified in the warrant." United States v. Walser, 275 F.3d

981, 986 (10th Cir. 2001), cert. denied, 535 U.S. 1069 (2002).

"[A] computer search 'may be as extensive as reasonably required

to locate the items described in the warrant'" based on probable

cause (emphasis added). United States v. Grimmett, 439 F.3d

1263, 1270 (10th Cir. 2006), quoting United States v. Wuagneux,

683 F.2d 1343, 1352 (11th Cir. 1982), cert. denied, 464 U.S. 814

(1983).

In the instant case, the police presented evidence in the

warrant affidavit that included the statements of witnesses to

the effect that the defendant had been receiving threatening

communications on his iPhone with respect to money he owed to

"people," and indeed had been using his iPhone while arguing

with an individual immediately prior to the shooting. This was

admittedly sufficient to establish probable cause to believe

that the defendant's iPhone likely contained evidence of

multiple contentious communications between himself and other

persons in the days leading up to the shooting, that is,

evidence of communications both received as well as initiated
 13

and sent by the defendant that would link him and others to that

shooting. The warrant, in turn, included authorization to

search for such evidence not only in the iPhone's call history

and text message files, but also in its photograph files.

The defendant contends, however, that the police had

probable cause only to search his telephone call and text files,

and not his photograph file. We disagree. Communications can

come in many forms including photographic, which the defendant

freely admits. So long as such evidence may reasonably be found

in the file containing the defendant's photographs, that file

may be searched.12,13 We agree with the motion judge that the

12
Photographs received or sent as attachments to texts may
be stored in the iPhone's photograph file as well as in the text
file. In addition, the iPhone can take photographs of texts,
which then are stored in the photograph file.
13
Although some of our case law discussing searches of
physical containers has employed language of "reasonableness,"
see, e.g., Commonwealth v. Signorine, 404 Mass. 400, 405 (1989)
("It is clear that a valid search may include any area, place,
or container reasonably capable of containing the object of the
search"), in practice, most fixed premises cases still analyze
whether the physical container at issue was "capable of
containing the object of the search" (emphasis added). Id.,
quoting United States v. Percival, 756 F.2d 600, 612 (7th Cir.
1985). See Commonwealth v. Wills, 398 Mass. 768, 774 (1986)
(photograph album "could have concealed a small knife" [emphasis
added]). Given the differences between searches of physical and
virtual places, at a minimum, the standard that governs the
proper scope of a search of an electronic device, such as the
iPhone here, for evidence for which probable cause has been
found is whether that evidence might reasonably be found in the
electronic files searched; "capable of containing" is far too
broad.
 14

evidence sought, for which there was probable cause, might

reasonably have been found in the photograph file. Therefore, a

search for such evidence in that file was neither outside the

scope of the warrant nor unreasonable.

Nevertheless, the defendant contends that a search using

the Universal Forensic Extraction Device (UFED) could easily

have been conducted for communications, including photographic

communications, without reviewing his photograph file.14 As

explained by the defense expert at the evidentiary hearing, the

UFED is capable of performing targeted searches of this type,

distinguishing between areas of the iPhone from which to extract

data -- such as "call logs," "phonebooks," "[short message

service],"15 "pictures," and "videos" -- and retrieving

photographs that may have been attached to text messages.

While it may be possible for a forensic examiner to

retrieve some photographic evidence through searches of files

other than the photograph file, that does not make such a

14
The Universal Forensic Extraction Device (UFED) connects
to a cellular telephone by a cable and has a port for insertion
of a memory drive, on which extracted information can be stored.
When connected and turned on, the UFED offers the examiner a
choice of extraction methods.
15
In selecting short message service as the type of data to
extract using the UFED, the police would have access to the
content of both simple texts and "multimedia message service"
texts with photographs or other items attached, regardless of
whether they had been saved or deleted.
 15

retrieval method constitutionally required where such

photographic evidence would also reasonably be found in the

iPhone's photograph file. In addition, the communications at

issue may have occurred over an extended period of time leading

up to the shooting, and where texts and their attachments may be

overwritten by new data, the saved photographic attachment may

only be found in the iPhone's photograph file. Accordingly, in

determining the nexus between the items sought and the place to

be searched, it was reasonable here to infer that the targeted

evidence might not exist exclusively in the text and call log

folders. See Commonwealth v. O'Day, 440 Mass. 296, 302 (2003)

(magistrate may make probable cause determination in part based

on "normal inferences as to where a criminal would be likely to

hide [evidence of the crime]" [citation omitted]). The

affidavit in question contained enough information from which

the magistrate and the forensic examiners could conclude that

the evidence sought might reasonably be located in the

photograph file. See McDermott, 448 Mass. at 767.

The dissent postulates that even if the warrant did

authorize the search and seizure of photographs, such

authorization extended, at most, to photographs depicting

threats. Post at . However, there is no conceivable way for

the police to detect whether a picture is of a threatening

nature without opening it first. See United States v. Burgess,
 16

576 F.3d 1078, 1094 (10th Cir.), cert. denied, 558 U.S. 1097

(2009). Once the photographs in question were viewed, their

evidentiary relevance linking the defendant (holding a gun and

wearing a jacket similar to the one worn by the shooter) to the

specific crimes under investigation was apparent. The

photographs also came within the scope and subject matter of the

warrant, as one or more of them could well have been sent as a

threatening communication to the person or persons who had

apparently been threatening him over several days.16

The motion to suppress was properly denied.17

So ordered.

16
We need not resort to the plain view doctrine in this
case, and we recognize that the application of that doctrine to
digital file searches may, at times, need to be limited, see
Preventive Med. Assocs. v. Commonwealth, 465 Mass. 810, 831-832
(2013); United States v. Comprehensive Drug Testing, Inc., 621
F.3d 1162, 1176 (9th Cir. 2010).
17
While the scope of the search in this instance might have
been unreasonable if the photographs had been discovered as the
result of reviewing photographs received, taken, or stored long
before the events leading up to the shooting, there is no
argument that that occurred here.
 LENK, J. (dissenting, with whom Duffly and Hines, JJ.,

join). The architects of art. 14 of the Massachusetts

Declaration of Rights and the Fourth Amendment to the United

States Constitution had in mind only searches of physical places

and seizures of physical objects. Transposing these protections

to digital contexts is an ongoing and challenging task, as the

matter before us only underscores. I disagree with the court's

resolution of the issues presented here. In my view, the search

of the photograph files on the defendant's Apple iPhone "smart"

cellular telephone was not supported by probable cause, and the

warrant authorizing that search was not sufficiently particular.

Furthermore, even had there been probable cause to support a

search of the photograph files, the photographs seized by the

police appear to have been outside the permissible scope of the

warrant. I write separately for these reasons, and also to

express my concern about the future direction of our search and

seizure law in a digital context.

In an increasingly digital world, we continue to lean

heavily on analogies between digital media and physical spaces

and objects, such as that between a computer and a closed

container. See, e.g., Commonwealth v. McDermott, 448 Mass. 750,

771-772, cert. denied, 552 U.S. 910 (2007) (McDermott). In

reality, however, searches of physical spaces for physical
 2

objects are akin to searches of digital media for digital

information much in the way that "a ride on horseback" resembles

"a flight to the moon." Riley v. California, 134 S. Ct. 2473,

2488 (2014) (Riley). As a result, if we are to preserve the

values that art. 14 and the Fourth Amendment seek to protect, we

must view more critically our reliance on physical analogs,

which may hamper rather than enhance our analyses; we also must

be amenable to considering new paradigms that may advance our

thinking. See generally Kerr, An Equilibrium-Adjustment Theory

of the Fourth Amendment, 125 Harv. L. Rev. 476 (2011).

1. Probable cause. Probable cause requires "a

'substantial basis' . . . for concluding that 'the items sought

are related to the criminal activity under investigation, and

that they reasonably may be expected to be located in the place

to be searched'" (citation omitted). Commonwealth v. Kaupp, 453

Mass. 102, 110 (2009) (Kaupp). The digital media at issue in

this case,1 however, do not fit neatly within this framework.

1
The photographs that the defendant seeks to suppress were
seized as the result of a three-part process. First, soon after
the shooting in which the defendant was wounded, police searched
his apartment pursuant to a warrant and seized his iPhone, among
other items. Next, pursuant to a separate warrant, a Boston
police department forensic examiner used a targeted data
extraction technique to copy certain categories of files from
the iPhone. Finally, the extracted files were studied to
 3

What was the "place" to be searched -- the defendant's iPhone as

a whole? Or only certain parts of it? And what were the

"items" to be seized -- categories of files? Or were they

certain files, perhaps specific photographs of evidentiary

value? See Kerr, Searches and Seizures in a Digital World, 119

Harv. L. Rev. 531, 551-557 (2005) (Kerr, Digital World)

(discussing meaning of digital "search"). See generally Kerr,

Executing Warrants for Digital Evidence: The Case for Use

Restrictions on Nonresponsive Data, Tex. Tech L. Rev.

(forthcoming) (on pages 23-28 of manuscript, discussing meaning

of digital "seizure").

As the court acknowledges, the warrant at issue here does

not provide easy answers to these questions. Ante at note 3.

The property that the warrant authorized the police to search

for and seize consisted principally of enumerated categories of

files, including "saved and deleted photographs."2 The warrant

determine whether they contained the information sought. The
search and seizure at issue here encompass the second and third
of these stages, as the first stage was conducted pursuant to a
separate warrant, not now contested.
2
Each photograph on the iPhone is stored in a separate
file. The other categories of files listed in the warrant were
the iPhone's "contact list, address book, calendar, date book
entries, group list, speed dial list, phone configuration
 4

stated that these files were located "on an Apple iPhone"

described by its physical appearance, which itself was situated

at the Boston police department building in the Hyde Park

section of Boston. Yet the warrant also incorporated by

reference an affidavit that appeared to envision a broader,

content-based search of the device. The affidavit concluded

that probable cause existed to believe the defendant's iPhone

contained "valuable information" linking the defendant and his

interlocutor to the crime.

Given this lack of clarity, the court correctly determines

that the warrant for the iPhone describes the place to be

searched as the physical device itself, and the items to be

seized as the categories of files that it lists. See ante at

note 3. The court incorrectly holds, however, that there was

probable cause to search the entire set of photograph files on

the defendant's iPhone. In my view, there was not a substantial

basis for concluding that the entire set of the defendant's

photograph files, rather than just the subset of photograph

information and settings, incoming and outgoing draft[,] sent,
[and] deleted text messages, saved, opened, unopened[,] draft[,]
sent[,] and deleted electronic mail messages, mobile instant
message chat logs and contact information[, and] mobile internet
browser."
 5

files attached to the defendant's text and multimedia messages,

was related to the criminal activity under investigation.3

An affidavit in support of a search warrant must be read

"in an ordinary, commonsense manner, without hypertechnical

analysis." See Commonwealth v. Cruz, 430 Mass. 838, 840 (2000),

and cases cited. This principle applies even where a search

ventures into the vast store of private information available on

a device like an iPhone. The probable cause analysis is limited

to "the facts recited in the affidavit and any reasonable

inferences therefrom." Kaupp, supra at 107, citing Commonwealth

v. Allen, 406 Mass. 575, 578 (1990).

Read in an ordinary, commonsense manner, and without

resorting to hypertechnical analysis, the facts in the affidavit

and the reasonable inferences to be drawn from them did not

provide probable cause to search the entire set of the

defendant's photograph files. In addition to recounting other

facts concerning the shooting, the affidavit reported, based on

the statements of three individuals, that the defendant had been

receiving threatening telephone calls and text messages, and

3
Review of the denial of a motion to suppress is
appropriate where, as here, "the ultimate findings and rulings
bear on issues of constitutional dimension." Commonwealth v.
McDermott, 448 Mass. 750, 762 (2007), quoting Commonwealth v.
Haas, 373 Mass. 545, 550 (1977), S.C., 398 Mass. 806 (1986).
 6

that he had been arguing on the telephone shortly before the

shooting. This information provided probable cause to believe

only that the iPhone's files pertaining to calls and text

messages would offer evidence of communications linking the

defendant to the shooting. The iPhone's lists of incoming,

outgoing, and missed calls could have shed light on the

identities of the individuals threatening the defendant and

arguing with him. Its text message files could have provided

similar information, and also could have revealed the content of

some threats made against the defendant. According to the

forensic expert, extraction of the text message files also would

have retrieved any photographs attached to those messages, see

ante at note 15, and the defendant has no quarrel with that

fact.

What the affidavit did not provide was reason to believe

that the iPhone's entire set of photograph files, as opposed to

only those photograph files attached to calls or text messages,

would present evidence related to the shooting. In the

abstract, I do not disagree with the court's statement that

"[c]ommunications can come in many forms including

photographic." Ante at . Nor, apparently, does the

defendant. A photograph depicting a severed horse's head, for
 7

instance, might well be used to communicate a threat (in the

mode of "The Godfather" novel and motion picture). But the

hypothetical viability of communication by photographic

suggestion, even had it been mentioned in the affidavit, would

not have supported a reasonable, commonsensical inference that a

search of the defendant's entire set of photograph files was

needed to produce the subset of photographs that might at some

point have been communicated.

The court reasons that, if a photograph file attached to a

text message had been deleted and overwritten by new data,

access to the entire set of photograph files on the iPhone might

be necessary for a forensic investigator to find another copy of

that specific file on the device. Ante at . As the court

notes, however, there is no argument that the photographs at

issue here were "received, taken, or stored long before the

events leading up to the shooting" -- the situation in which, in

the ordinary course, photographs that had been attached to text

messages would have been most likely to have been deleted and

overwritten by new data.4 See ante at note 17.

4
In some circumstances, it might be natural to suspect that
data deliberately has been concealed from inquiring eyes. See,
e.g., United States v. Gray, 78 F. Supp. 2d 524, 527 n.5 (E.D.
Va. 1999) (discussing investigation of hacking offenses). The
 8

In sum, the information presented to the magistrate did not

create even a "[s]trong reason to suspect" that the entire set

of photograph files on the defendant's iPhone were related to

the criminal activity being investigated, much less a

"substantial basis" for such a belief (citations omitted). See

Kaupp, supra at 110-111, and cases cited. The search of those

files was not supported by probable cause, and consequently it

was unconstitutional.5

While there was surely probable cause to believe that there

was evidence of the communications described in the affidavit

somewhere within the defendant's iPhone, the essence of the

United States Supreme Court's decision in Riley, supra, was that

facts set forth in the affidavit circumscribing our analysis,
however, did not suggest that data concealment was otherwise a
concern in this case. In any event, when an initial search
leads a forensic investigator to believe that files have been
deleted or otherwise concealed, the investigator of course may
seek an additional warrant to perform a more far-reaching search
for those files.
5
The Commonwealth argues that suppression is not warranted
even if the search for the defendant's photograph files was
improper. "We have not adopted the 'good faith' exception for
purposes of art. 14 of the Massachusetts Declaration of Rights
or statutory violations, focusing instead on whether the
violations are substantial and prejudicial." Commonwealth v.
Hernandez, 456 Mass. 528, 533 (2010). But "all violations
of . . . probable cause requirements are substantial."
Commonwealth v. Sheppard, 394 Mass. 381, 389 (1985). See
Commonwealth v. Nelson, 460 Mass. 564, 571 (2011).
 9

such devices cannot be treated like ordinary containers. This

is because "a cell phone search would typically expose to the

government far more than the most exhaustive search of a house."

Riley, supra at 2491. In one commentator's words, "limiting a

search to a particular computer is something like . . . limiting

a search to the entire city." Kerr, Digital Evidence and the

New Criminal Procedure, 105 Colum. L. Rev. 279, 303 (2005).

We must not be taken in by the shape and size of a device

that permits access to massive stores of information of

different kinds. Where possible -- recognizing that it not

always is -- it may be best to treat such a device more like a

city than like a packing crate. Here, there was no impediment

to limiting the search to certain types and categories of files

stored in specific sections of the iPhone's data storage.

Because there was no substantial basis for believing that the

entire set of photograph files on the defendant's iPhone

contained evidence related to the shooting, that portion of the

iPhone should not have been included in the "place" to be

searched.

2. Particularity. Article 14 and the Fourth Amendment

also require that a warrant identify with particularity the
 10

place to be searched and the items to be seized. The requisite

particularity, however, was not present in this case.6

Read commonsensically, the affidavit and warrant both

envisioned a general search of the entire iPhone, rather than a

targeted search for certain types of communications. Based on

the facts it presents, the affidavit draws the general

conclusion that the defendant's iPhone "contains valuable

information that will link the [defendant] and [another person]

to the crime." The affidavit proceeds to explain that,

accordingly, permission is being sought to search the iPhone for

a wide variety of categories of files. Several of these, such

as the defendant's "[s]peed dial list," "[p]hone configuration

information and settings," and "[m]obile Internet browser," were

most unlikely to contain any evidence of the criminal activity

under investigation. The warrant, in turn, authorized the

6
The court declines to consider the defendant's
particularity arguments to the extent they were not raised in
the Superior Court. See ante at note 8. However, these
arguments were fairly raised: the defendant argued specifically
that "[t]he particularity requirement serves as a safeguard
against general exploratory rummaging by the police through a
person's belongings," quoting Commonwealth v. Freiberg, 405
Mass. 282, 298, cert. denied, 493 U.S. 940 (1989). In addition,
he contended that "the warrant became an impermissible general
search." Contrast Commonwealth v. Garcia, 409 Mass. 675, 678-
679 (1991) ("An issue not fairly raised before the trial judge
will not be considered for the first time on appeal").
 11

seizure of most of the categories of files on the defendant's

iPhone, including all "saved and deleted photographs."7

Allowing the police to search a broad variety of categories

of files, many of which were at most tangentially related to the

communications described in the affidavit, was an "end run"

around the particularity requirement. Particularity should mean

more than just a general directive to the police to look until

they find something.

Creating particularized limitations beforehand for a search

of a device capable of storing hundreds of thousands of files is

difficult. But it is not impossible. As the court

acknowledges, current search technology already allows forensic

examiners to pinpoint their searches. Ante at .

Accordingly, the warrant could have limited the search only to

the iPhone's call records and text message files -- the

categories of files most likely to provide evidence of the

"threatening phone calls and threatening text messages" that

7
With regard to the reasonableness of the search's
execution, it also may be noted that video recording files were
extracted from the iPhone even though those files were not named
in the warrant either as places to be searched or as items to be
seized. See ante at note 6.
 12

preceded the shooting.8 The warrant also could have limited the

search of any images files temporally to include only images

stored on the device in the days or weeks leading up to the

shooting. Compare United States v. Winn, 79 F. Supp. 3d 904,

921 (S.D. Ill. 2015) ("Most importantly, the warrant should have

specified the relevant time frame"). Restrictions of this sort

would prevent forensic investigators from exercising greater

discretion than art. 14 and the Fourth Amendment allow. As the

United States Supreme Court noted in Riley, supra at 2495, the

8
Courts in other jurisdictions have taken this approach.
See United States v. Winn, 79 F. Supp. 3d 904, 922 (S.D. Ill.
2015) (deeming warrant overbroad that did not limit seizure to
"a very small and specific subset of data" or "describe that
data with as much particularity as the circumstances allowed").
See also Matter of Black iPhone 4, 27 F. Supp. 3d 74, 79-80
(D.D.C. 2014) (requiring government to provide greater
particularity with respect to procedures that would be used to
avoid viewing material outside scope of warrant to search
iPhone); State v. Henderson, 289 Neb. 271, 289 (2014), cert.
denied, 135 S. Ct. 2845 (2015) (concluding that warrant for
search of cellular telephone "must be sufficiently limited in
scope to allow a search of only that content that is related to
the probable cause that justifies the search"). Cf. Preventive
Med. Assocs. v. Commonwealth, 465 Mass. 810, 829 (2013)
(permitting use of "taint team" to screen out privileged
electronic mail messages prior to review by investigator or
prosecutor). The United States Court of Appeals for the Tenth
Circuit concluded in United States v. Burgess, 576 F.3d 1078,
1094 (10th Cir.), cert. denied, 558 U.S. 1097 (2009), that
review after the fact of the reasonableness of a given search
satisfied the particularity requirement, but acknowledged that
such review "may be problematic" in some contexts. Requiring a
particularized warrant beforehand avoids these potential
problems.
 13

fact that technology now enables an individual to store huge

sums of information in his or her pocket "does not make the

information any less worthy of the protection for which the

Founders fought."

3. Scope of the search. Finally, the photographs that the

defendant seeks to suppress do not seem to have been within the

scope of the search that the court deems permissible. Two of

the four photographs at issue apparently show the defendant in

possession of a gun, and two show him wearing a green jacket.

It is possible that these images provided some measure of

support for the inference that the defendant had participated in

the shooting, since witnesses had seen one of the shooters

wearing a green shirt or jacket. See ante at . The

photographs were not, however, the kind of evidence that the

police were (according to the court) permitted to be searching

for -- namely, communications relating to the shooting.

The court accordingly devises the hypothesis that the

contested photographs "could well have been sent as a

threatening communication to the person or persons who had

apparently been threatening [the defendant]." Ante at .

This hypothesis is implausible. The court's theory is not

rooted in an evaluation of the photographs, given that they are
 14

not part of the record before us. The Commonwealth, having

examined the photographs, has not suggested that they

constituted, singly or together, a "threatening communication"

made by the defendant to anyone. Nor does the available

information support such an interpretation.

The affidavit described three interviews concerning the

communications for which, on the court's view, the warrant

authorized a search. According to the first interview, the

defendant "received a [tele]phone call and started arguing with

the caller on the [tele]phone," and "left the apartment still

arguing with the caller" shortly before the shooting took place.

According to the second interview, the defendant "was receiving

threatening [tele]phone calls and threatening text messages on

his [tele]phone." According to the third interview, the

defendant had "been getting a lot of telephone threats because

he owe[d] money to people."

These interviews do not support the view that the

photographs in question were included in the communications

described. The first interview clearly described a telephone

call rather than an exchange of picture messages. While the

second and third interviews did not rule out the possibility

that the threats described were communicated in photographs,
 15

both interviews specified that the threats were received, not

sent. Nothing in the affidavit suggests that the defendant was

using photographs of himself to threaten others. Moreover, even

if the two photographs of the defendant holding a gun were

intended as a threat, it strains credulity to assert that

photographs of the defendant wearing a green jacket had a

similar purpose. In sum, I question whether the forensic

investigators reasonably could have understood the photographs

at issue to be communications related to the shooting. By

extension, the photographs would not be ones that the

investigators were, on the court's analysis, permitted to seize.

A corresponding flaw occurring in a physical search could

have been cured by the "plain view" doctrine, according to

which, "if officers, in the course of conducting a lawful

search, discover evidence in plain view, such evidence may be

seized." See McDermott, supra at 777, citing United States v.

Gray, 78 F. Supp. 2d 524, 528 (E.D. Va. 1999). Yet, recognizing

that "the application of that doctrine to digital file searches

may, at times, need to be limited," ante at note 16, and sources

cited, the court resists wholesale importation of the plain view

doctrine into the current context.
 16

There is good reason for the court's caution on this score.

Although the search at issue in this case was, according to the

court, limited to "evidence of communications that would link

the defendant and another person to the shooting," ante at

note 3, the plain view doctrine would render that constraint

meaningless, given that "there is no conceivable way" to detect

whether a picture is relevant evidence without first looking at

it. See ante at .

It is an open question whether application of the plain

view doctrine to searches of digital media would undermine the

constitutional prohibition on general searches.9 This court

applied the plain view doctrine to a search of computer files in

McDermott, supra at 777. More recently, however, the court

expressed concern that a search of digital files could be

"joined with the plain view doctrine to enable the Commonwealth

to use against defendants inculpatory evidence . . . even though

9
See, e.g., United States v. Galpin, 720 F.3d 436, 451 (2d
Cir. 2013); United States v. Comprehensive Drug Testing, Inc.,
621 F.3d 1162, 1176-1177 (9th Cir. 2010); Note, Digital Searches
and the Fourth Amendment: The Interplay Between the Plain View
Doctrine and Search-Protocol Warrant Restrictions, 49 Am. Crim.
L. Rev. 301 (2012); Note, Computer Seizures and Searches:
Rethinking the Applicability of the Plain View Doctrine, 83
Temple L. Rev. 1097 (2011). See also United States v. Ganias,
755 F.3d 125, 137-140 (2d Cir. 2014), reh'g en banc granted, 791
F.3d 290 (2015) (government not permitted to retain indefinitely
nonresponsive documents seized in permissible search).
 17

such evidence may not actually fit within the scope of the

search warrants obtained." Preventive Med. Assocs. v.

Commonwealth, 465 Mass. 810, 831-832 (2013) (Preventive Med.

Assocs.). This prospect is worrisome because searches of

digital information tend to require law enforcement to delve

into, and carefully sift through, large stores of data. See

United States v. Comprehensive Drug Testing, Inc., 621 F.3d

1162, 1176-1177 (9th Cir. 2010). The result is that "rules

created to prevent general searches for physical evidence may

result in the equivalent of general searches for digital

evidence." Kerr, Digital World, supra at 566.

In Preventive Med. Assocs., supra at 832, this court

elected to "leave for another day the question whether use of

the plain view doctrine as a justification for admission of

evidence should be precluded or at least narrowed in the context

of searches for electronic records." While not today, the day

when the court will be called upon to determine more precisely

when and how the plain view exception applies to digital

searches is likely close at hand.