U NITED S TATES AIR F ORCE
             C OURT OF C RIMINAL APPEALS
                          ________________________

                               No. ACM 39232
                          ________________________

                            UNITED STATES
                                Appellee
                                      v.
                        Zhermie R. TOLEDO
          Technical Sergeant (E-6), U.S. Air Force, Appellant
                          ________________________

        Appeal from the United States Air Force Trial Judiciary
                         Decided 16 October 2018
                          ________________________

Military Judge: James R. Dorman.
Approved sentence: Bad-conduct discharge, confinement for 2 years, for-
feiture of all pay and allowances, and reduction to E-1. Sentence ad-
judged 18 January 2017 by GCM convened at Minot Air Force Base,
North Dakota.
For Appellant: Major Allen S. Abrams, USAF.
For Appellee: Lieutenant Colonel Joseph J. Kubler, USAF; Captain Mi-
chael T. Bunnell, USAF; Mary Ellen Payne, Esquire.
Before HARDING, HUYGEN, and POSCH, Appellate Military Judges.
Senior Judge HARDING delivered the opinion of the court, in which
Judges HUYGEN and POSCH joined.
                          ________________________

    This is an unpublished opinion and, as such, does not serve as
    precedent under AFCCA Rule of Practice and Procedure 18.4.
                          ________________________

HARDING, Senior Judge:
   Contrary to Appellant’s pleas, a general court-martial consisting of a mili-
tary judge convicted Appellant of attempted enticement of a person to engage
                       United States v. Toledo, No. ACM 39232


in sexual acts with him in exchange for money, attempted receipt of child por-
nography, attempted production of child pornography, and procuring persons
to engage in sexual acts with him in exchange for money in violation of Articles
80 and 134, Uniform Code of Military Justice (UCMJ), 10 U.S.C. §§ 880, 934. 1
The military judge sentenced Appellant to a bad-conduct discharge, confine-
ment for two years, forfeiture of all pay and allowances, and reduction to the
grade of E-1. The convening authority approved the sentence as adjudged.
    On appeal, Appellant raises the following assignments of error: (1) whether
the military judge erred when he found probable cause existed to search Ap-
pellant’s camera; (2) even if there was probable cause to search Appellant’s
camera, whether the military judge erred when he found the search of the
memory card within the camera was within the scope of the search authorized
by the magistrate’s warrant; 2 and (3) whether the evidence supporting Appel-
lant’s convictions is legally and factually sufficient where the prosecution was
required to prove a person was under the age of 18 years and where the prose-
cution introduced no evidence to show Appellant’s conduct was of a nature to
bring discredit upon the armed forces or prejudicial to good order and disci-
pline. 3 We hold that the military judge erred in finding a substantial basis for
probable cause to search the memory card of Appellant’s camera and that nei-
ther the good faith exception nor the inevitable discovery exception to the war-
rant requirement applies. Thus, we set aside Charge II and its Specification
(patronizing prostitutes) and the sentence. Finding no other prejudicial error,
we affirm the remaining findings.

                                     I. BACKGROUND
   Appellant answered an online advertisement placed on a website used for
advertising prostitution services by Officer KC of the Minot (North Dakota)


1The military judge acquitted Appellant of two other specifications of attempted con-
spiracy to perform a sexual act on a child who had not attained the age of 12 years and
a lewd act upon a person he believed had not attained the age of 16 years in violation
of Article 80, UCMJ.
2   Given our resolution of the first issue, we do not address this assignment of error.
3 Appellant raises these issues of legal and factual sufficiency pursuant to United
States v. Grostefon, 

(C.M.A. 1982). Given our disposition of Charge II and
its Specification we need not reach these issues for that conviction. With respect to
Specifications 1, 2, and 3 of Charge I, we have considered and reject these claims, which
neither require additional analysis nor warrant relief. See United States v. Matias, 

, 363 (C.M.A. 1987).




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                      United States v. Toledo, No. ACM 39232


Police Department as part of an undercover law enforcement operation. The
advertisement posted under the pseudonym “Riley” was captioned, “Petite
young browneyed [sic] girl…Teach me Daddy! –18” and included photographs
of a young woman. Appellant’s text-message response to the advertisement
consisted of a question—whether “Riley” was really 18—and Appellant stated
his preference as to age as “younger would be better” or words to that effect.
Officer KC, posing as “Riley,” replied that she was 16 years-old. Appellant im-
mediately requested pictures and replied that “Riley’s” age was “great.” Appel-
lant then specifically asked for pictures consisting of “Riley’s” 16 yo [sic] boobs
and kitty.” As the text messaging continued, Appellant identified himself as
“Robin” and described sex acts he was willing to pay “Riley” $250.00–$400.00
per hour to perform on or with him. Appellant also texted that he desired to
videotape these sex acts with “Riley.”
    After review of the texts, Minot Police Department officers searched social
media websites for the phone number associated with Appellant’s texts to “Ri-
ley” and found a social media page for “Robin Toledo.” An officer recognized
“Robin Toledo” as an Air Force member she knew as “Zhermie.” In response to
a request for information, the Air Force Office of Special Investigations detach-
ment at Minot Air Force Base, North Dakota, confirmed that a Technical Ser-
geant Zhermie Robin Toledo was assigned to Minot Air Force Base and that he
had a phone number that matched the one associated with the texts to “Riley.”
    Appellant and “Riley” continued to correspond, and only a few days after
Appellant had initially responded to the online advertisement, made arrange-
ments to meet in a hotel parking lot. Appellant messaged “Riley” that, before
going to a room with her, he wanted to “do a law enforcement check” in the
parking lot and that he would be driving a black truck. Officer TJ, who por-
trayed “Riley” for the meeting with Appellant, observed a black truck enter the
parking lot of the agreed-upon hotel. She recognized the person driving the
truck as the person in the photographs posted on the social media page associ-
ated with the phone number Appellant used to send texts to “Riley.” Officer TJ
approached Appellant’s truck and said, “Hi.” Appellant responded, “Hi Riley,
I’m Robin.” Almost immediately, other officers who had been observing nearby
apprehended Appellant by removing him from the truck, handcuffing him, and
laying him on the ground. In the course of patting down Appellant, officers
detected and examined bulges in Appellant’s pockets. The officers removed
$300.00 in cash and a video-camera from Appellant’s pockets. Meanwhile, an-
other officer secured Appellant’s wallet and cell phone from his truck. Appel-
lant was arrested for the offense of luring a minor by computer or other elec-
tronic means. 4


4   N.D. Cent. Code § 12.1–20–05.1 (2007).


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                   United States v. Toledo, No. ACM 39232


    Nearly a week after Appellant’s arrest, Captain DS of the Minot Police De-
partment requested a search warrant for the digital contents of Appellant’s
cellphone and camera. No search of either took place prior to the search war-
rant being issued. At a hearing for the Defense motion to suppress the evidence
resulting from the search of Appellant’s cell phone and camera, the trial coun-
sel asked Captain DS about seeking a search warrant for the camera.
       Trial Counsel (TC): Why would you need a search warrant?
       Captain DS (DS): To make sure that we're not violating the con-
       stitutional rights of the defendant.
       TC: And why in this case did you think that those items needed
       to be searched.
       DS: He had remarked on the text conversations that he wanted
       to video record their [Appellant and “Riley’s”] sexual activity.
       TC: Did you believe that there might be evidence of a crime on
       the camera that was taken off his person?
       DS: Yes.
       TC: What were you basing this believe [sic] off of?
       DS: Well, for one thing his text said that he wanted to videotape
       it and it’s fairly common for people to be involved in this kind of
       activity to have multiple encounters and other types of media.
       TC: Would you say that your experience as a police officer and
       as the commander of investigations has taught you that that’s
       typical?
       DS: Yes.
       TC: Did you think that it was reasonable under these circum-
       stances to have the camera searched.
       DS: Yes.
       TC: And when you obtained the search warrant, did you feel
       that you were legally authorized at the point to go ahead and
       conduct, or have those searches conducted?
       DS: Yes.
    In Captain DS’s affidavit to the search authority, Captain DS recited per-
tinent parts of Appellant’s texts with “Riley” and the details of Appellant’s ap-
prehension and stated that he believed “the cell phone and the camera may
contain evidence of the instant offense”—luring a minor by computer or other
electronic means. Captain DS further stated that he believed “the camera may


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                    United States v. Toledo, No. ACM 39232


contain evidence of child pornography or other sexual offenses based upon [Ap-
pellant’s] text message that he wanted to videotape the sexual activity with
[“Riley”].”
    A North Dakota district court judge authorized the requested search. The
search warrant by its terms authorized a search and seizure of “the premises
known as: Samsung Verizon cell phone” and “Sony cyber-shot camera” for “ev-
idence of identification of the owner, text messages, call history, photos, child
pornography.” 5 The search warrant also specifically authorized a forensic ex-
amination of the contents of Appellant’s cell phone and “any external multi-
media storage devices” used with the phone. This particularized provision re-
garding multi-media storage devices was not repeated for the camera. The
search warrant stated as a basis for probable cause that Captain DS had rea-
son to believe that “on the premises known as: Samsung Verizon cell phone”
and “Sony cyber-shot camera” there was property being concealed; namely, ev-
idence of identification of ownership, text messages, call history, photos, and
child pornography.
    After receiving search authorization, but before turning over Appellant’s
cell phone and camera memory card to Detective CH for forensic analysis, Cap-
tain DS viewed the content of the memory card of the camera. Captain DS did
not find any evidence in the camera memory card of the “instant offense” of
luring a minor or any evidence of child pornography. Captain DS did, however,
find six videos of Appellant engaged in sex acts with two different adult women,
one of whom Captain DS recognized as a suspected prostitute. Captain DS did
not examine the cell phone.
    Detective CH used software to extract data from Appellant’s cell phone and
prepared reports of Appellant’s text messaging to other cell phones. The re-
ports generated from the extracted data were organized by the cell phone num-
bers to which Appellant’s cell phone sent text messages. These reports were
produced in a searchable portable document format (PDF). Only one of these
PDF extraction reports matched the text messaging between Appellant and
“Riley,” and was readily identifiable by “Riley’s” cell phone number and the
timeframe of the messaging between Appellant and “Riley”—both data points
known to the Minot Police Department. This extraction report, consisting of
five pages, was admitted as Prosecution Exhibit 3. The other reports of text
messages extracted from Appellant’s phone, which matched cell phone num-




5Nowhere in Captain DS’s affidavit does he indicate that the search authorization was
sought in order to search for and seize “evidence of identification of the owner.”


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                   United States v. Toledo, No. ACM 39232


bers other than “Riley’s,” included messages that detailed solicitations, negoti-
ations, and agreements between Appellant and people Appellant believed to be
prostitutes.
    During closing argument, the trial counsel referenced metadata regarding
the dates and times of certain text messaging from Appellant’s cell phone and
correlated that data to the date and time stamps of the videos that were stored
on the camera memory card depicting Appellant engaged in sex acts with sus-
pected prostitutes. Having established this link between the text messages and
videos, the trial counsel argued to the military judge that Appellant had on
divers occasions patronized prostitutes as alleged in Charge II and its Specifi-
cation.

                                II. DISCUSSION
A. Search of Appellant’s Camera
   Appellant asserts that the Government did not have a substantial basis for
probable cause to search the memory card of Appellant’s camera and that nei-
ther the good faith exception nor the inevitable discovery exception to the war-
rant requirement applies, and therefore the military judge erred in denying
the motion to suppress the videos from Appellant’s camera memory card. We
agree.
   1. Substantial Basis for Probable Cause
   The Fourth Amendment provides as follows:
       The right of the people to be secure in their persons, houses, pa-
       pers, and effects, against unreasonable searches and seizures,
       shall not be violated, and no Warrants shall issue, but upon
       probable cause, supported by Oath or affirmation, and particu-
       larly describing the place to be searched and the persons or
       things to be seized.
U.S. CONST. amend. IV.
    Searches conducted pursuant to either a warrant or an authorization based
on probable cause are presumed reasonable. United States v. Hoffmann, 

, 123–24 (C.A.A.F. 2016) (quoting United States v. Wicks, 

,
99 (C.A.A.F. 2014)).
    We review a military judge's denial of a motion to suppress for an abuse of
discretion. 

(citing United States v. Keefauver, 

, 233
(C.A.A.F. 2015)). Accordingly, when reviewing a magistrate’s issuance of a
search authorization, we “do not review [the military magistrate's] probable
cause determination de novo.” 

Instead, we examine whether a “mag-
istrate had a substantial basis for concluding that probable cause existed.”

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                   United States v. Toledo, No. ACM 39232


United States v. Rogers, 

, 164–65 (C.A.A.F. 2009) (citing United
States v. Bethea, 

, 187 (C.A.A.F. 2005)). We give “great deference”
to the magistrate’s probable cause determination because of “the Fourth
Amendment’s strong preference for searches conducted pursuant to a war-
rant.” United States v. Nieto, 

, 105 (C.A.A.F. 2017) (citation omit-
ted). However, this deference is “not boundless,” and a reviewing court may
conclude that “the magistrate’s probable-cause determination reflected an im-
proper analysis of the totality of the circumstances.” 

States
v. Leon, 

, 915 (1984)). “Sufficient information must be presented
to the magistrate to allow that official to determine probable cause; his action
cannot be a mere ratification of the bare conclusions of others.” Gates, 

, 239 (1983); see United States v. Gallo, 

, 424 (C.A.A.F. 2001).
However, if a military magistrate has “a substantial basis to find probable
cause, a military judge [does] not abuse his discretion in denying a motion to
suppress.” United States v. Leedy, 

, 213 (C.A.A.F. 2007). A substan-
tial basis exists “when, based on the totality of the circumstances, a common-
sense judgment would lead to the conclusion that there is a fair probability
that evidence of a crime will be found at the identified location.” 

(citations omitted).
    The Court of Appeals for the Armed Forces (CAAF) has addressed the issue
of substantial basis for probable cause to search and seize evidence stored on
electronic media in several cases.
   In Leedy, the CAAF considered whether the description by the appellant’s
roommate of the file titles he had seen on the screen of the appellant’s com-
puter, coupled with an experienced investigator’s knowledge of digital child
pornography, provided a substantial basis for a probable cause determination.
The investigator provided generalized information regarding child pornogra-
phy file names and electronic storage. The CAAF concluded the information
provided a substantial basis for the magistrate to conclude that there was prob-
able cause to believe that child pornography would be found on the appellant’s
computer, even without a specific description of the file 

.
    In Hoffmann, the CAAF considered whether evidence of acts of child en-
ticement and “an intuitive relationship between [such acts] and the possession
of child pornography” could provide a substantial basis for concluding that
there was probable cause to believe the appellant possessed child pornography
on his electronic 

(quoting United States v. Hoffmann, 

, 555 (N.M. Ct. Crim. App. 2014)). Noting an absence of any evidence
or direct link connecting the acts of child enticement to the possession of child
pornography on the electronic media seized, the CAAF found the facts before
the search authority insufficient to provide a substantial basis for concluding


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                   United States v. Toledo, No. ACM 39232


that there was probable cause to believe the appellant possessed child pornog-
raphy on his electronic media. 

    In Nieto, the appellant was observed and later admitted to using his cell
phone to record others using a latrine without their consent. Based on this
information and a law enforcement officer’s generalized profile on how “per-
sons who view and record sexual acts often times store and catalog their im-
ages and videos on larger storage devices such as a computer or hard drive,” a
military magistrate authorized the search of the appellant’s laptop 

. The search of the computer revealed nothing relevant to the
investigation of the latrine recordings but did yield videos and pictures that
constituted evidence of other crimes. In reviewing whether the authorizing
magistrate had a substantial basis to find probable cause, the CAAF found that
the affidavits supporting the search authorization did not reference any data
transfers from the appellant’s cell phone to his laptop computer, and thus the
CAAF concluded the “generalized profile was not based on a firm factual foun-
dation.” 

(emphasis added). The CAAF then underscored the im-
portance of facts to a substantial basis for probable cause.
       In order to identify a substantial basis for concluding that prob-
       able cause existed to believe that Appellant’s laptop was linked
       to the crime, we conclude that—at a minimum—there needed to
       be some additional showing, such as the fact that Appellant ac-
       tually downloaded images (illicit or otherwise) from his cell
       phone to his laptop, stored images on his laptop, or transmitted
       images from his laptop. And yet, there was no such showing in
       this case.

    In the case now before us, the Government relies on the fact that Appellant
“was actively seeking and trying to produce child pornography” with his stated
intent to videotape the sex acts with “Riley” and the fact he brought a video-
camera to their meet-up in order to demonstrate that the judge who authorized
the search of Appellant’s camera memory card relied on more than just a gen-
eralized law enforcement behavioral profile or “an intuitive relationship” be-
tween certain facts to find probable cause. The Government then cites United
States v. Colbert, 

(8th Cir. 2010), as persuasive authority for the
conclusion that the weight of Appellant’s attempted production of child pornog-
raphy tipped the balance in favor of a substantial basis for probable cause to
search the camera memory card. However, as the CAAF pointed out in Hoff-
man, reliance on Colbert is problematic if the facts of the instant case are con-
siderably different from the facts of Colbert.




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                   United States v. Toledo, No. ACM 39232


       Colbert conversed for forty minutes with a five-year-old girl he
       met in the park, telling her that he had movies and videos in his
       apartment that she would like to see. During a consent search of
       his vehicle, police found handcuffs and other police-type gear.
       The Eighth Circuit held that, although a close case, the affidavit
       established probable cause by showing a direct link between the
       alleged enticement of a child and movies in his apartment, the
       place searched pursuant to a search warrant.

. The CAAF concluded “[t]hat link [was] not present
in [Hoffman].” 

the facts of Appellant’s case are more closely aligned with those of
Hoffmann and Nieto and distinguished from those of Colbert and Leedy. There
was no direct factual link between Appellant’s interactions with “Riley” and
any data stored on Appellant’s camera or camera memory card. As the military
judge correctly determined in his written ruling that denied the motion to sup-
press,
       [A]t the time of the issuance of the warrant, there was little rea-
       son to believe that the camera contained evidence of the offense
       for which [Appellant] was apprehended – the enticement of “Ri-
       ley.” [Appellant] had not yet completed the meet-up with “Riley,”
       and had not had an opportunity to film any interaction between
       himself and “Riley.”
Notwithstanding this finding of fact, the military judge analyzed the infor-
mation presented to the judge who authorized the search of Appellant’s camera
and found a substantial basis for probable cause:
       At the time the search warrant was issued, the issuing Judge
       had before him information that [Appellant] had (1) arranged to
       have sex with an underage girl, (2) has expressed a desire or in-
       terest in videotaping the encounter, and (3) was apprehended at
       the meeting site with a camera in his possession. From this, the
       Judge found probable cause to believe that there might be evi-
       dence of other similar crimes on the camera.
       ....
       There was no need for the Judge, in issuing a warrant, to rely
       upon faulty “intuitive relationships” between child enticement
       and child pornography, as there was sufficient independent evi-
       dence of an intent and attempt to produce child pornography to
       support a finding of probable cause that other evidence of similar
       crimes might be on the camera.



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                     United States v. Toledo, No. ACM 39232


    We disagree that Appellant’s failed attempt to produce child pornography
with the camera at issue provided a substantial basis for concluding that prob-
able cause existed to search the same camera. Unlike the appellant in Colbert
who told the five-year-old girl that he had movies in his apartment, and thus
provided a direct factual link between his child enticement activities and the
search of his apartment for those videos, there was no direct factual link be-
tween Appellant’s interactions with “Riley” and the search of Appellant’s cam-
era memory card. Unlike the search of the appellant’s computer in Leedy for
child pornography based on file names observed on the screen of the very same
computer, Minot police had no information to indicate what might be on Ap-
pellant’s camera memory card. Instead, they relied on a hunch that Appellant
would have previously produced child pornography with the same video-cam-
era and stored it on the camera memory card.
     Appellant’s case resembles not Colbert or Leedy but Nieto, 6 where a re-
quired minimal showing—that the appellant “actually downloaded images (il-
licit or otherwise) from his cell phone to his laptop, stored images on his laptop,
or transmitted images from his laptop”—was not made, and thus there was not
a substantial basis to support a probable cause search of the laptop computer.

. We reach a similar conclusion here. There was no factual
showing that Appellant actually produced child pornography with his video-
camera and stored it on the camera memory card. Captain DS’s affidavit pro-
vided no basis, substantial or otherwise, for the judge who issued the warrant
to conclude that probable cause existed to search the camera memory card. 7




6We note that Nieto was decided by the CAAF the month after Appellant’s trial. Thus
the military judge, who distinguished this case from the facts of Hoffmann, did not
have Nieto available for his consideration in determining whether there was a sub-
stantial basis for probable cause.
7 Although not argued at trial by the Government or found by the military judge as a
basis for probable cause, the Government argues on appeal that the search of Appel-
lant’s camera “was valid because it was reasonable to think the camera would contain
evidence of ownership.” We are not persuaded. Captain DS did not request search au-
thorization for the camera in order to search for and seize “evidence of identification of
the owner.” The camera was seized from the possession of Appellant at the time of his
arrest and was an instrumentality of the offense of attempted production of child por-
nography. Appellant’s possession of the camera corroborated his text messaging
wherein he indicated his desire to videotape the sex acts with “Riley.” Ownership of
the camera was not in dispute. We can only conclude that the language in the war-
rant—“evidence of identification of the owner”—appears there either unintentionally
because of the use of a template or intentionally to expand the basis beyond what was
presented by and/or sought by the affiant. Neither possibility comports with the re-
quirements of the Fourth Amendment.


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                    United States v. Toledo, No. ACM 39232


    2. Good Faith
   The military judge found at trial and the Government argues on appeal
that, even if there was no probable cause to search Appellant’s camera, the
good faith exception applies. We disagree.
    For the good-faith exception to apply, the Government must establish that
law enforcement's reliance on a defective authorization is objectively reasona-
ble. 

. The Government has the burden of establishing
by a preponderance of the evidence the following: (1) the seizure resulted from
a search and seizure authorization issued, in relevant part, by a magistrate;
(2) the magistrate had a substantial basis for determining probable cause ex-
isted; and (3) law enforcement reasonably and in good faith relied on the au-
thorization. Mil. R. Evid. 311(c)(3), 311(d)(5)(A); 

; see also
United States v. Carter, 

, 420 (C.A.A.F. 2001) (citation omitted).
     As explained above, the judge issuing the search warrant in Appellant’s
case did not have a substantial basis for determining the existence of probable
cause, the second requirement for application of the good-faith exception. Fur-
ther, Captain DS stated in his affidavit that he believed “the camera may con-
tain evidence of the instant offense”—luring a minor by computer or other elec-
tronic means—even though Minot police had information that Appellant lured
“Riley” only by the electronic means of cell phone text messaging and appre-
hended Appellant before Appellant could make any recording with the camera.
This assertion by Captain DS is demonstrably untrue, and yet it was relied
upon by the judge to issue the search warrant in this case. After examination
of the affidavit and search warrant through the “eyes of a reasonable law en-
forcement official,” we find Captain DS did not have an objectively reasonable
belief that the judge had a substantial basis for determining the existence of
probable cause to search the camera. Carter, 54 M.J at 422. Thus, we conclude
that the Government failed to establish the Minot Police Department’s reliance
on the defective search warrant was objectively reasonable. The good faith ex-
ception does not apply to justify the search of Appellant’s camera. 8 See Hoff-

.
    3. Inevitable Discovery
   The Government also argues that, because there was probable cause to
search Appellant’s cell phone for text messages between Appellant and “Riley,”
“even if the authorization to search the camera were obtained improperly, it


8Recognizing the tension between the discussion of the good-faith exception in Hoff-

–28, and 

–22, we conclude that under either
understanding of the good-faith doctrine, the Government has not met its burden of
establishing this exception to the exclusionary rule in Appellant’s case.


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                   United States v. Toledo, No. ACM 39232


would have been obtained by another lawful means.” While we agree that the
search of Appellant’s cell phone for evidence of luring a minor (text messages
with “Riley”) was supported by probable cause, we disagree that discovery of
the videos on Appellant’s camera as evidence of patronizing adult prostitutes
inevitably and lawfully flowed from that search.
    “The doctrine of inevitable discovery creates an exception to the exclusion-
ary rule allowing admission of evidence that, although obtained improperly,
would have been obtained by another lawful means.” United States v. Wallace,

(C.A.A.F. 2008) (citing Nix v. Williams, 

, 444 (1984)).
“M.R.E. 311(b)(2) embodies this exception, stating that ‘[e]vidence that was ob-
tained as a result of an unlawful search or seizure may be used when the evi-
dence would have been obtained even if such unlawful search or seizure had
not been made.’” 

original). For the inevitable discovery doc-
trine to apply, the Government must establish by a preponderance of the evi-
dence “that when the illegality occurred, the government agents possessed, or
were actively pursuing, evidence or leads that would have inevitably led to the
discovery of the evidence and that the evidence would inevitably have been
discovered in a lawful manner had not the illegality occurred.” 

(citations omitted).
   The Government argues that, in searching Appellant’s cell phone, investi-
gators would have had to “sift through all of the captured data to find the rel-
evant text messages” and that “in doing so they would have found abundant
evidence that Appellant engaged in [patronizing prostitutes] and made specific
arrangements to videotape his sexual liaisons with multiple prostitutes.” This
assertion by the Government, however, is directly rebutted by the testimony of
Detective CH. The extraction reports were created and organized by cell
phones numbers. The relevant text messages stored on Appellant’s phone were
readily identifiable by “Riley’s” cell phone number and a specific date range—
20 April 2015 to 24 April 2015. We find that the “sifting” of all of Appellant’s
data from his cell phone was not necessary to find the “Riley” text messages.
    “The Fourth Amendment requires that a search warrant describe the
things to be seized with sufficient particularity to prevent a general explora-
tory rummaging in a person's belongings.” United States v. Richards, 

, 369 (C.A.A.F. 2017) (citing United States v. Carey, 

, 1272
(10th Cir.1999)). In Richards, the CAAF considered whether a search authori-
zation was overly broad in failing to limit the dates of communications being
searched on electronic devices. In so doing, the CAAF affirmed that the Fourth
Amendment’s particularity requirement for warrants and the prohibition
against general searches apply to search authorizations for electronic devices.
The CAAF also recognized, however, the distinct issues of how incriminating
evidence may be located on electronic devices and “the dangers of too narrowly


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                   United States v. Toledo, No. ACM 39232


limiting where investigators can go.” 

While reluctant to prescribe
ex ante limitations or require particular search methods and protocols for elec-
tronic devices, the CAAF found such searches subject to an ex post reasonable-
ness analysis. 

States v. Christie, 

, 1167 (10th
Cir. 2013)) (“[E]ven if courts do not specify particular search protocols up front
in the warrant application process, they retain the flexibility to assess the rea-
sonableness of the search protocols the government actually employed in its
search after the fact, when the case comes to court, and in light of the totality
of the circumstances.”).
       In charting how to apply the Fourth Amendment to searches of
       electronic devices, we glean from our reading of the case law a
       zone in which such searches are expansive enough to allow in-
       vestigators access to places where incriminating materials may
       be hidden, yet not so broad that they become the sort of free-for-
       all general searches the Fourth Amendment was designed to
       prevent.

the totality of the circumstances in this case, we find
the search of Appellant’s cell phone and the PDF extraction reports beyond the
readily identifiable “Riley” texts captured in the report specific to “Riley’s”
phone number violated the prohibition against general searches. Thus, we find
the text messages containing references to Appellant’s desire to video-record
sex acts with prostitutes were obtained in violation of the Fourth Amendment.
The linchpin of the Government’s inevitable discovery claim has been pulled
out and its wheels have slipped off the axle.
    Assuming arguendo that the search of Appellant’s phone was not a general
search, the discovery of another crime in the course of the search had its own
Fourth Amendment implications. In United States v. Osorio, 

(A.F.
Ct. Crim. App. 2008), this court addressed requirements regarding search war-
rants for computers—and by extension for stored electronic or digital media—
when evidence of another crime is discovered.
       [T]here must be specificity in the scope of the warrant which, in
       turn, mandates specificity in the process of conducting the
       search. Practitioners must generate specific warrants and
       search processes necessary to comply with that specificity and
       then, if they come across evidence of a different crime, stop their
       search and seek a new authorization. This was not done in this
       case, therefore the search was invalid.

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                     United States v. Toledo, No. ACM 39232


    The Minot Police Department had probable cause to search Appellant’s cell
phone, but only for evidence of his crimes connected to “Riley.” Assuming it
was necessary and reasonable under the Fourth Amendment to search the non-
”Riley” extraction reports, at the instant they discovered even a single text
message between Appellant and a person other than “Riley” that constituted a
solicitation, negotiation, or agreement for that person to engage in a sex act
with Appellant in exchange for money or other compensation, they had evi-
dence of a different crime than the one they were investigating. Having discov-
ered a different crime, they were obligated to stop the search and seek new
authorization. They did not do so, and thus at that point the continued search
of Appellant’s cell phone became unlawful.
    The record does not establish when evidence of a crime not involving “Riley”
was first discovered on Appellant’s cell phone. Moreover, it is impossible to
determine from the record at what point in the cell phone search the investi-
gators found the first non-”Riley” text-message reference to videotaping—the
direct link that would have been necessary to establish a substantial basis for
probable cause to search the camera.
    We conclude that the search of Appellant’s cell phone for anything more
than the text messages with “Riley” was unlawful. We further conclude that
the Government has failed to show by a preponderance of the evidence (1) that,
when the illegality occurred, the Minot Police Department possessed or was
actively pursuing evidence or leads that would have inevitably led to the dis-
covery of the camera videos that evidenced Appellant’s patronizing adult pros-
titutes, and (2) that the evidence from Appellant’s camera would inevitably
have been discovered in a lawful manner had not the illegality occurred.
    In summary, we conclude that the judge who issued the search warrant did
not have a substantial basis to determine that probable cause existed to search
Appellant's camera, and that the good faith and inevitable discovery exceptions
do not apply in this case. Thus, the military judge abused his discretion in
denying the motion to suppress the evidence of the videos found on Appellant’s
camera. 9
B. Prejudice
    Although we have determined the military judge erred by admitting the
evidence from Appellant’s camera, we may not set aside the guilty finding
based on that evidence “unless the error materially prejudices the substantial
rights of the accused.” Article 59(a), UCMJ, 10 U.S.C. § 859(a).


9We have also concluded that the benefits of appreciable deterrence of future, unlawful
searches outweigh the costs to the justice system of exclusion of the evidence. Mil. R.
Evid. 311(a)(3).


                                          14
                    United States v. Toledo, No. ACM 39232


  In this case, because the admission of the videos violated the Fourth
Amendment, the error was of a constitutional dimension.
       A constitutional error is harmless when it appears beyond a rea-
       sonable doubt that the error complained of did not contribute to
       the verdict obtained. . . . “To say that an error did not ‘contribute’
       to the ensuing verdict is not, of course, to say that the jury was
       totally unaware of that feature of the trial later held to have
       been erroneous. . . . To say that an error did not contribute to the
       verdict is, rather, to find that error unimportant in relation to
       everything else the jury considered on the issue in question, as
       revealed in the record.”
Hoff

(citations omitted).
    In order for Appellant to be found guilty of the offense of patronizing a pros-
titute under Article 134, UCMJ, the Government was required to prove, among
other elements, that Appellant engaged in a sexual act with another person
who was not Appellant’s spouse. The videos discovered on Appellant’s camera
provided direct evidence of Appellant engaged in such acts. We cannot say the
error did not contribute to the military judge finding Appellant guilty of pat-
ronizing a prostitute, and thus it was not harmless beyond a reasonable doubt.
As such, we set aside the findings as to Charge II and its Specification.
    Although the cell phone search was not raised as an issue by Appellant, our
consideration of the Government’s claim of inevitable discovery leads us to con-
clude that the non-”Riley” texts (the balance of the Government evidence for
Charge II and its Specification) were also obtained in violation of the Fourth
Amendment. As there remains no admissible evidence in the record to support
a prosecution for the offense of patronizing a prostitute under Article 134,
UCMJ, a rehearing of the set-aside findings is not appropriate. Charge II and
its Specification are dismissed with prejudice.
C. Sentence Rehearing
   Having dismissed Charge II and its Specification, we consider whether,
consistent with United States v. Winckelmann, 

, 12 (C.A.A.F. 2013),
we should reassess the sentence or return this case for a sentence rehearing.
We are not confident we can accurately reassess an appropriate sentence.
    Pursuant to 

–16, we use the following four fac-
tors to guide our determination whether to reassess a sentence and apply them
to Appellant’s case:




                                        15
                   United States v. Toledo, No. ACM 39232


   •   Dramatic changes in the penalty landscape and exposure: As a result of
       the dismissal of Charge II and its Specification, the maximum imposa-
       ble sentence to confinement was reduced by one year from 42 to 41
       years.
   •   Whether an appellant chose sentencing by members or a military judge
       alone: Appellant was sentenced by a military judge.
   •   Whether the nature of the remaining offenses captures the gravamen
       of criminal conduct included within the original offenses and, in a re-
       lated manner, whether significant or aggravating circumstances ad-
       dressed at the court-martial remain admissible and relevant to the re-
       maining offenses: Appellant still stands properly convicted of three at-
       tempted offenses—patronizing a prostitute, receipt of child pornogra-
       phy, and production of child pornography. Each of these attempted of-
       fenses concerned “Riley” and combined capture the gravamen of Appel-
       lant’s criminal conduct. The evidence of text messages and videos sup-
       porting the dismissed specification, however, would not be admissible
       as aggravation evidence for the attempt convictions.
   •   Whether the remaining offenses are of the type that we have experience
       and familiarity with to reliably determine what sentence would have
       been imposed at trial: Unlike drug offense convictions for example, this
       court has little experience with reviewing sentences for the offense of
       patronizing a prostitute.
    We are convinced the dismissed offense did contribute to Appellant’s ad-
judged sentence. While the penalty landscape did not change dramatically, Ap-
pellant was sentenced by a military judge, and the remaining offenses captured
the gravamen of criminal conduct, we are not confident we can gauge the ex-
tent of that contribution, given our limited experience with the review of sen-
tences for the offense of patronizing a prostitute. Therefore, considering the
facts of Appellant’s case and the totality of the circumstances, we find we are
not able to determine to our satisfaction that, “absent any error, the sentence
adjudged would have been of at least a certain severity . . . .” United States v.
Sales, 

, 308 (C.M.A. 1986). Having so found, we set aside the sen-
tence and authorize a rehearing as to the sentence.




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                     United States v. Toledo, No. ACM 39232


                                 III. CONCLUSION
    The findings as to Charge II and its Specification and the sentence are SET
ASIDE. The remaining findings are AFFIRMED. A rehearing as to the set-
aside sentence is authorized. Article 66(e), UCMJ, 10 U.S.C. § 866(e). 10


                  FOR THE COURT



                  CAROL K. JOYCE
                  Clerk of the Court




10We order sealed Prosecution Exhibit 21, a disc containing sexually explicit videos of
Appellant and adult women. The Government will ensure that any copy of Prosecution
Exhibit 21 in the possession of the Government, Appellant, or any counsel in the case
and any other known copy is destroyed.


                                          17