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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 selfdefense 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 sixtyfour 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.