Title: Commonwealth v. Dorelas
Citation: N/A
Docket Number: SJC-11793
State: Massachusetts
Issuer: Massachusetts Supreme Court
Date: January 14, 2016

NOTICE:  All slip opinions and orders are subject to formal 
revision and are superseded by the advance sheets and bound 
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error or other formal error, please notify the Reporter of 
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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.