No IN THE UNITED STATES COURT OF APPEALS FOR THE FOURTH CIRCUIT. UNITED STATES OF AMERICA, Plaintiff/Appellee,

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 1 of 70 No. 15-4111 IN THE UNITED STATES COURT OF APPEALS FOR THE FOURTH CIRCUIT UNITED STATES OF AMERICA, Plaintiff/Appellee, v. ALI SABOONCHI, Defendant/Appellant. On Appeal from e United States District Court for e District of Maryland, Souern Division (The Honorable Paul W. Grimm) BRIEF OF APPELLANT JAMES WYDA Federal Public Defender District of Maryland MEGHAN SKELTON Appellate Attorney 6411 Ivy Lane, Suite 710 Greenbelt, MD 20770 (301) 344-0600 Counsel for Appellant

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 2 of 70 TABLE OF CONTENTS Page Table of Auorities................................................. iv Jurisdictional Statement.............................................. 1 Issues Presented..................................................... 2 Statement of The Case................................................ 2 A. When Mr. Saboonchi crossed e United States border, e government seized his digital media, en several days later, conducted a warrantless search of e data..................... 3 B. The District Court rejected Mr. Saboonchi s proposed jury instruction at would have defined willfulness as knowingly and intentionally violating a known legal duty...................... 6 Summary of Argument............................................... 8 Standard of Review................................................. 10 Argument......................................................... 10 I. The warrantless search of data contained in Ali Saboonchi s smart phones and USB drive violated e Four Amendment............... 10 A. Balancing e extensive intrusion into an individual s substantial privacy interest against e government s interests at e border, e Four Amendment requires a warrant supported by probable cause for is search...................................... 12 1. An individual s privacy interest in data stored in and accessible rough a cell phone is extensive.............. 13 i

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 3 of 70 a. Quantity..................................... 13 b. Quality...................................... 14 2. The government s interest in protecting e integrity of e border is also substantial............................. 18 3. When it comes to searching cell phone data, Riley fundamentally alters e balance between e government s interest and e individual s Four Amendment rights..... 19 B. Because is search was e equivalent of an exhaustive search of a home, it exceeded e scope of a border search............... 22 C. Oer considerations also demonstrate at is search exceeded e scope of a valid warrantless border search.................. 25 1. Searches pursuant to warrant exceptions must be narrowly tailored to a specific goal............................. 25 2. This search bore no relationship to e justifications for e border search exception.............................. 28 3. The time and place of is search also establish at e search was too attenuated from e purposes of e exception to render e warrantless search reasonable...... 32 D. If e court decides at e Four Amendment requires only reasonable suspicion, e search is still unreasonable because e district court misapplied at standard here.................... 35 1. When reasonable suspicion supports warrantless nonroutine border searches, e suspicion must arise at e border and relate to e purposes of e exception......... 36 2. Warrantless searches based on reasonable suspicion must have a limited duration............................... 40 ii

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 4 of 70 3. The facts here do not amount to reasonable suspicion...... 41 II. The District Court improperly instructed e jury regarding e mens rea element of e offense by defining willfully as general knowledge of unlawfulness raer an an intentional violation of a known legal duty....................................................... 44 A. The statutory and regulatory scheme at defines e crime of exporting to an embargoed country is a labyrinine and sometimes contradictory web............................... 45 B. To save is virtually impenetrable web of regulations from unconstitutional vagueness, e government must prove a specific intent mens rea of willfulness to secure a conviction............ 48 C. The jury instructions here incorrectly defined willfulness......... 52 Conclusion........................................................ 58 Certificate of Compliance............................................ 60 Certificate of Service iii

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 5 of 70 TABLE OF AUTHORITIES Cases Page(s) Almeida-Sanchez v. United States, 413 U.S. 266 (1973).............. 19, 28, 32 Arizona v. Gant, 556 U.S. 332 (2009)................................... 25 Bryan v. United States, 524 U.S. 184 (1998)....................... 54, 55, 56 Carroll v. United States, 267 U.S. 132 (1925)................... 19, 26, 27, 28 Cheek v. United States, 498 U.S. 192 (1991)......................... passim Chimel v. California, 395 U.S. 752 (1969)............................... 23 Florida v. Wells, 495 U.S. 1 (1990).................................... 31 Furie Operating Alaska, LLC v. Department of Homeland Security, 2014 WL 1289581 (D. Ala. 2014).................................... 34 Go-Bart Importing Co. v. United States, 282 U.S. 344 (1931)............... 23 Gunnells v. Healplan Servs. Inc., 348 F.3d 417 (4 Cir. 2003)............. 53 In re Grand Jury Subpoena Duces Tecum, 670 F.3d 1335 (11 Cir. 2012)....................................... 40 Kremen v. United States, 353 U.S. 346 (1957)......................... 23, 33 Kyllo v. United States, 533 U.S. 27 (2001)............................ 17, 24 Maryland v. King, 133 S. Ct. 1958 (2013)............................... 22 Minnesota v. Dickerson, 508 U.S. 336 (1993)............................ 25 iv

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 6 of 70 New York v. Burger, 482 U.S. 691 (1987)............................... 32 Poland Bros. Inc. v. United States, 64 Cust. ct. 248, 253, 1970 WL 14611 (Cust. Ct. 1970)................... 34 Riley v. California, 134 S. Ct. 2473 (2014).......................... passim Segura v. United States, 468 U.S. 796 (1984)............................ 26 Staples v. United States, 511 U.S. 600 (1994)............................ 53 Terry v. Ohio, 392 U.S. 1 (1968)................................... passim United States v. 12 200-Foot Reels of Super 8mm Film, 413 U.S. 123 (1973)............................................... 27 United States v. Aguebor, 166 F.3d 1210 (4 Cir. 1999).................... 27 United States v. Alavi, Case No. 2:07-cr-429-NVD (D. Ariz.)................ 57 United States v. Amirnazmi, 645 F.3d 564 (3d Cir. 2011)................... 48 United States v. Aragon, 155 F.3d 561 (4 Cir. 1998)...................... 27 st United States v. Aversa, 984 F.2d 493 (1 Cir. 1993)....................... 54 United States v. Bishop, 740 F.3d 927 (4 Cir. 2014)................... 55, 56 United States v. Brennan, 538 F.2d 711 (5 Cir. 1976)..................... 30 United States v. Breza, 308 F.3d 430 (4 Cir. 2002)....................... 10 United States v. Brodie, 403 F.3d 123 (3d Cir. 2005)...................... 49 United States v. Brown, 415 F.3d 1257 (11 Cir. 2005)..................... 53 United States v. Camou, 773 F.3d 932 (9 Cir. 2014)...................... 26 v

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 7 of 70 United States v. Cortez, 449 U.S. 411 (1981)....................... 27, 36, 37 United States v. Cotterman, 709 F.3d 952 (9 Cir. 2013)............... passim United States v. Edmonds, 240 F.3d 55 (D.C. Cir. 2001).................... 37 United States v. Elashyi, 554 F.3d 480 (5 Cir. 2008)...................... 49 United States v. Flores-Montano, 541 U.S. 149 (2004)............... 18, 27, 34 United States v. Frade, 709 F.2d 1387 (11 Cir. 1983)..................... 49 United States v. Graham, F.3d, 2015 WL 4637931 (4 Cir. 2015)...................... passim United States v. Hassanshahi, 75 F. Supp. 3d 101 (D.D.C. 2014)....... 36, 38, 40 United States v. Humphries, 308 Fed. Appx. 892 (6 Cir. 2009).............. 27 United States v. Ickes, 393 F.3d 501 (4 Cir. 2005).................... passim United States v. Jones, 132 S. Ct. 945 (2012)............................. 15 United States v. Kaczmarak, 62 Fed. Appx. 510 (4 Cir. 2003).............. 27 United States v. Kim, F. Supp. 2d 2015 WL 2148070 (D.D.C. 2015)............... 26, 28, 43 United States v. Leo, 792 F.3d 742 (7 Cir. 2015)......................... 40 United States v. Macko, 994 F.2d 1526 (11 Cir. 1993).................... 49 United States v. Martinez-Fuerte, 428 U.S. 543 (1976)..................... 27 United States v. Mattio, 17 F.2d 879 (9 Cir. 1927)........................ 34 United States v. Modanlo, Case No. 9:10-cr-295-PJM (D. Md.).............. 57 vi

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 8 of 70 United States v. Montoya de Hernandez, 473 U.S. 531 (1985)........... passim United States v. Mousavi, Case No. 2:07-cr-00513-PA (C.D. Cal.)............ 57 United States v. Ogberaha, 771 F.2d 655 (2d Cir. 1985).................... 37 United States v. Oriakhi, 57 F.3d 1290 (4 Cir. 1995)...................... 27 United States v. Place, 660 F.2d 44 (2d Cir. 1981)........................ 33 United States v. Pomponio, 429 U.S. 10 (1976)........................... 50 United States v. Ramsey, 431 U.S. 606 (1977)........................ passim United States v. Robinson, 414 U.S. 218 (1973).......................... 21 United States v. Sharpe, 470 U.S. 675 (1985)............................ 41 United States v. Sonmez, 777 F.3d 684 (4 Cir. 2015)...................... 10 United States v. Spence, 199 F.3d 1329 (4 Cir. 1999)..................... 27 United States v. Switzer, 11 Fed. Appx. 65 (4 Cir. 2001)................... 27 United States v. Taylor, 584 Fed. Appx. 47 (4 Cir. 2014).................. 27 United States v. Walden, 146 F.3d 489 (7 Cir. 1998)...................... 36 United States v. Warshak, 631 F.3d 266 (6 Cir. 2011)......................... 14 Vernonia School Dist. 47J v. Acton, 515 U.S. 646 (1995)................... 31 Walter v. United States, 447 U.S. 649 (1980)............................. 32 Statutes and Rules First Amendment................................................... 31 vii

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 9 of 70 Four Amendment............................................. passim 18 U.S.C. 3231.................................................... 1 18 U.S.C. 3742.................................................... 1 28 U.S.C. 1291.................................................... 1 50 U.S.C. 1701................................................... 45 50 U.S.C. 1702................................................. 2, 45 50 U.S.C. 1705................................................. 2, 45 50 U.S.C. 1705(c)................................................. 45 31 C.F.R. 560.203............................................... 2, 45 31 C.F.R. 560.204............................................ 2, 45, 48 Executive Order 12957.............................................. 45 Executive Order 12959.............................................. 45 Executive Order 13059.............................................. 45 viii

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 10 of 70 15-4111 IN THE UNITED STATES COURT OF APPEALS FOR THE FOURTH CIRCUIT UNITED STATES OF AMERICA, Plaintiff/Appellee, v. ALI SABOONCHI, Defendant/Appellant. On Appeal from e United States District Court for e District of Maryland, Souern Division (The Honorable Paul W. Grimm) BRIEF OF APPELLANT JURISDICTIONAL STATEMENT The district court had jurisdiction under 18 U.S.C. 3231. That court entered final judgment on February 11, 2015. (JA 2898.) Ali Saboonchi filed a timely notice of appeal on February 24, 2015. (JA 2904.) This Court has jurisdiction under 28 U.S.C. 1291 and 18 U.S.C. 3742. 1

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 11 of 70 ISSUES PRESENTED I. When Ali Saboonchi crossed e border into e United States, e government seized his digital media, including an iphone and USB drive. Days later, wiout a warrant, government agents made a complete digital copy of all e data, en conducted a forensic search. Was e warrantless search unreasonable under e Four Amendment? II. The government charged Mr. Saboonchi wi knowingly and willfully violating e Iran trade embargo. He asked for a jury instruction requiring e government to prove at he knew what e embargo prohibited, but wilfully violated e embargo anyway. (JA 572). Did e district court err in instructing at jury at e government need not prove at Mr. Saboonchi was aware of e contents of e regulatory scheme? STATEMENT OF THE CASE A grand jury charged Ali Saboonchi wi multiple counts of violating e Iran trade embargo, in violation of 50 U.S.C. 1702, 1705 and 31 C.F.R. 560.203, 1 560.204. (JA 29-49.) A jury convicted him on all counts. He now appeals his conviction. 1 The combination of statutes and regulations comprising e embargo is known as e International Emergency Economic Powers Act (IEEPA) and Iranian Transactions and Sanctions Regulations (ITSR). 2

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 12 of 70 A. When Mr. Saboonchi crossed e United States border, e government seized his digital media, en several days later, conducted a warrantless search of e data. The FBI received a tip at, in e fall of 2010, someone named Ali made some inquiries about specialized technology at has industrial, medical, and military applications. (JA 226.) The FBI traced e phone number used in at inquiry to Ali Saboonchi. (JA 226.) A Homeland Security Investigations (HSI) special agent named Kelly Baird launched a criminal investigation into trade embargo violations and named Mr. Saboonchi as a person of interest. She en entered Mr. Saboonchi s name into a database at e Department of Homeland Security and Customs and Border Patrol (CBP) officers use to screen individuals and determine eir admissibility at e United States borders. (JA 337-38.) When she entered Mr. Saboonchi s name into e database, she had no information about wheer Mr. 2 Saboonchi planned to travel abroad. (JA 226.) Knowing at she did not have probable cause for any search, she wanted to position herself to be able to exploit a potential coincidental border crossing. (JA 221.) Several weeks later, during e evening of March 31, 2012, Agent Baird got a 2 After entering his name into e database, Agent Baird subpoenaed FedEx records and learned at Mr. Saboonchi had shipped what appeared to be industrial goods to e United Arab Emirates despite having told e supplier at e product s end user was domestic. (JA 228.) This transaction happened about a year before Agent Baird entered Mr. Saboonchi s name into e database. (JA 228.) 3

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 13 of 70 phone call from CBP Officer Kenne Burkhardt, who said at Mr. Saboonchi had arrived five minutes earlier at e Rainbow Bridge, a point of entry into e United 3 States in Buffalo, New York. (JA 169, 219.) Officer Burkhardt asked Agent Baird if she wanted anying particular done at e border, and she responded, I just instructed at if ere were any electronic media found, I would like it detained. (JA 221; see also JA 168.) She also asked e officer to send e devices to her in Baltimore. When she made at request, Agent Baird had no idea if Mr. Saboonchi had any cell phones or oer electronic media wi him. (JA 248.) She did not tell Officer Burkhardt to ask any specific questions or do anying else unusual. (JA 225.) At e suppression hearing later, she explained at I wanted to be able to look at e media pursuant to our border auority. (JA 221.) She furer explained at she wanted to see if ere was evidence of export violations... any evidence of criminality. (JA 225-26.) Officer Burkhardt seized e devices. He explained at e only reason he seized Mr. Saboonchi s cell phones and USB drive was because Agent Baird asked 3 Border Patrol officers routinely query e database discussed above. In doing so on is occasion, e primary inspection officer found Agent Baird s entry and referred Mr. Saboonchi to secondary inspection. (JA 166-67.) Officer Burkhardt conducted e secondary inspection. 4

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 14 of 70 him to. (JA 168, 171, 212.) He did not know, and she did not tell him, why she wanted him to seize e devices, nor did she explain why she had entered Mr. Saboonchi s name into e database. (JA 207.) He observed noing independently at e border at would have prompted him to seize e devices or even take a cursory glance rough e phones. (JA 187-89.) He in fact did not examine e contents of e phones or USB drive in any way. (JA 205.) Instead, right away, he gave e digital devices to a local Buffalo HSI agent. Meanwhile, Officer Burkhardt asked Mr. Saboonchi routine questions and conducted a routine seven-point search of Mr. Saboonchi s car. (JA 156, 169.) The sole prompting for any of is questioning and searching was e database entry. (JA 186.) Officer Burkhardt found noing of note in e car or on Mr. Saboonchi s person. (JA 169.) Agent Burkhardt learned at Mr. Saboonchi is a United States Citizen who had been visiting a college roommate in Buffalo. Mr. Saboonchi and his wife took a day trip to Niagara Falls. Everying about Mr. Saboonchi s trip struck Officer Burkhardt as common sightseeing; noing seemed at all unusual. (JA 191.) They carried no large sums of cash and carried no contraband. (JA 171, 184.) Officer Burkhardt characterized his interaction wi Mr. Saboonchi and his findings as absolutely routine. (JA 175, 178.) 5

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 15 of 70 Two days later, Agent Baird received an email from an HSI agent in Buffalo at e two smart phones and USB drive were on eir way to her in Baltimore via FedEx. (JA 222-23.) On April 4, 2012, she turned e devices over to a forensic examiner, who made a digital image of e devices. (JA 231.) She took a look at e data stored on e two smart phones and USB drive, en later reviewed e entire contents. (Id.) On April 13, 2012, she returned e two cell phones and e USB 4 drive to Mr. Saboonchi, but retained all e data in e form of e digital images. (JA 234.) She testified at she did not believe at she needed any reasonable suspicion of any unlawful activity in order to seize and conduct a forensic search of e digital media. (JA 242.) B. The District Court rejected Mr. Saboonchi s proposed jury instruction at would have defined willfulness as knowingly and intentionally violating a known legal duty. In his jury trial, Mr. Saboonchi contested few facts. For e most part, he agreed at e events at e government described actually occurred. He did not dispute at he had sent certain items to an intermediary country for transshipment to Iran. Nor did he dispute at e ITSR required a license to export e items. But he contested wheer he knew about at licensing requirement. (JA 2789, 2792.) The 4 Agent Baird testified at she eventually destroyed e digital image of e Sony Xperia, after reviewing e data from at phone, and deciding at it belonged to Mr. Saboonchi s wife. 6

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 16 of 70 crux of his defense was at he did not possess e specific intent mens rea. The government proposed an instruction regarding e intent element at stated, While e government must show at e defendant knew at his conduct was illegal, it is not necessary for e government to prove at e defendant had read, was aware of, or had consulted e specific regulations governing his activities. In oer words, e government is not required to prove at e defendant read, was aware of, or had consulted e ITSR and e licensing requirements at ose regulations describe. (JA 556.) Mr. Saboonchi objected to is instruction, arguing at it was inconsistent wi prevailing pattern instructions defining knowingly and willfully, and at it eliminated e required finding at Mr. Saboonchi knowingly and intentionally violated a known legal duty. He also argued at is instruction misinterpreted e statute and regulations at issue. (JA 571.) He proposed e instruction: To find at e defendant acted willfully, you must find beyond a reasonable doubt at he knew at his actions violated [e statute, regulations, and executive orders]. (JA 572.) The district court denied Mr. Saboonchi s request. (JA 2358-64.) The final jury instruction stated, While e government must show at e defendant knew at his conduct was unlawful, it is not necessary for e government to prove at e defendant had read or was aware of e contents of e [statute and regulations]. (JA 7

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 17 of 70 2631.) Thus, e instructions directly contradicted what Mr. Saboonchi had requested. SUMMARY OF ARGUMENT The warrantless search of all e data on Mr. Saboonchi s smart phones and USB drive was unreasonable under e Four Amendment. The border search exception does not excuse is warrantless search. Riley v. California changes e way courts must analyze warrantless searches of data on smart phones. Riley held at cell phones, as a category, are different from oer personal property subject to warrantless searches because of e vast quantity of profoundly personal and private data ey contain. Riley did not overrule e warrant exception at issue (a search incident to arrest), but assigned different weights to e interests at courts must balance when examining warrantless searches. The balance tilts in favor of e individual s interests because of e quantity and nature of e information exposed in a data search, despite e heightened governmental interest. Riley applies to is search. Like in Riley, e government has a heightened interest supporting warrantless searches at e border. But e individual s privacy interest in e data is identical. The Four Amendment balance erefore tilts in favor of e individual. Even if oer border searches do not, searching data from a 8

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 18 of 70 cell phone requires a warrant. In any event, under a more traditional border search analysis, is search was still unreasonable. The search exceeded e scope of a valid warrantless border search because it was not narrowly tailored to e justification for e exception. This search was unteered to e purposes behind e warrant exception. Moreover, it was unbounded by geography, scope, or duration. It began four days after Mr. Saboonchi crossed e border, took place 350 miles from where he crossed, lasted indefinitely, and assisted by technology, intruded comprehensively and deeply into a privacy interest at e Supreme Court has equated wi e privacy enshrined in a home. The district court also erred in refusing Mr. Saboonchi s requested jury instruction defining willfulness. When e government charges a crime based on complex regulatory schemes, like e Iran Trade Sanctions Regulations, it must prove at e defendant knew what e law stated, and knowingly and intentionally violated at known legal duty. Here, e court instructed e jury at it could convict Mr. Saboonchi if it decided at he knew, in general, at his conduct was unlawful. This instruction impermissibly watered down e intent element of e offense. It prejudiced Mr. Saboonchi because his entire defense was directed at intent. He did not deny e conduct; he denied knowing what e embargo prohibited and at he 9

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 19 of 70 chose to violate e embargo. STANDARD OF REVIEW Wheer a search is reasonable under e Four Amendment is a question of law at is Court reviews de novo. United States v. Breza, 308 F.3d 430, 433 (4 Cir. 2002). This Court reviews e denial of a defendant s requested jury instruction for abuse of discretion. United States v. Sonmez, 777 F.3d 684, 688 (4 Cir. 2015). To establish an abuse of discretion, e defendant must demonstrate at e proposed instruction (1) was correct; (2) was not oerwise covered by e instructions at e district court actually gave to e jury; and (3) failing to give e instruction impeded e defense. Id. ARGUMENT I. The warrantless search of data contained in Ali Saboonchi s smart phones and USB drive violated e Four Amendment. A Border Patrol officer seized Ali Saboonchi s iphone 4S, his wife s Sony Xperia smart phone, and a USB drive at e Rainbow Bridge in Buffalo, New York, when Mr. Saboonchi was returning from a sightseeing day trip to Niagara Falls. The officer did not search or inspect e contents of e devices at e border. Several days later, a different agent shipped e devices to Baltimore, where a computer 10

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 20 of 70 forensics expert produced a complete digital image of e devices, en examined all e data. Noing at occurred at e Rainbow bridge, noing about Mr. Saboonchi s trip, and noing found on Mr. Saboonchi s person or in his car at e border prompted e seizure or subsequent warrantless search of his data. (JA 171, 186-89, 191, 212.) Instead, government agents decided to conduct e sweeping search of his data weeks earlier, when ey entered his name into a database at prompts warrantless border searches, alough e agents did not even know if Mr. Saboonchi, a United States citizen, had any plans to travel abroad. (JA 226-28.) By entering Mr. Saboonchi s name into e database, government agents hoped to position emselves to exploit e border search doctrine, knowing ey did not have probable cause, to investigate what ey believed might have been past criminal conduct. For multiple overlapping reasons, e warrantless search of Mr. Saboonchi s 5 data violated e Four Amendment. Alough e government enjoys broad auority to conduct warrantless searches at e border, at power is not absolute. An individual s privacy interest in data especially e quantity and quality of data contained on a smart phone outweighs e government interest in conducting 5 The Four Amendment states at The right of e people to be secure in eir persons, houses, papers, and effects, against unreasonable searches and seizures, shall not be violated. 11

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 21 of 70 warrantless border searches. The highly intrusive nature of e search also impacts e constitutional balance in favor of e individual s privacy interests. The Four Amendment erefore requires a warrant based on probable cause in order to perform e search at occurred here. Anying less is constitutionally unreasonable. Moreover, e search exceeded e scope of a valid warrantless border search. It was a general rummaging for evidence of a past crime, unrelated to e purposes giving rise to e border exception. The bread and duration of e search far exceeds any border search at e Supreme Court has ever approved. A. Balancing e extensive intrusion into an individual s substantial privacy interest against e government s interests at e border, e Four Amendment requires a warrant supported by probable cause for is search. To assess wheer a search is reasonable, courts balance e intrusion into an individual s Four Amendment interests against e legitimate governmental interest at stake. United States v. Montoya de Hernandez, 473 U.S. 531, 539 (1985). See also Riley v. California, 134 S. Ct. 2473, 2484 (2014) ( We generally determine wheer to exempt a given search from e warrant requirement by assessing, on e one hand, e degree to which it intrudes upon an individual s privacy and, on e oer, e degree to which it is needed for e promotion of legitimate governmental interests. ) (internal quotation omitted). What is reasonable depends upon all of e 12

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 22 of 70 circumstances surrounding e search or seizure and e nature of e search or seizure itself. Montoya de Hernandez, 473 U.S. at 537. 1. An individual s privacy interest in data stored in and accessible rough a cell phone is extensive. Modern cell phones, as a category, implicate privacy concerns far beyond ose implicated by searches of oer property someone may carry on his or her person. Riley, 134 S. Ct. at 2488. Cell phones differ in bo a quantitative and a qualitative sense from oer objects. Id. at 2489. a. Quantity An individual s privacy interest in cell phone data is substantial simply because of e sheer quantity of information. A person s ability to carry around physical photographs, mail, videos, bank records, books and newspapers is necessarily limited, but e storage capacity of smart phones makes e impossible possible. An iphone like Mr. Saboonchi s allows a person to carry e equivalent of ousands of photographs, songs, videos, and/or millions of pages of text. These privacy interests are constantly growing because of technological 6 advances improving bo storage and functionality of cell phones. The gulf 6 For example, Mr. Saboonchi owned e fif generation of iphone. Since his model first became available to consumers, Apple has introduced ree more versions of iphone, and is expected to introduce anoer on September 9, 2015. 13

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 23 of 70 between physical practicability and digital capacity will only continue to widen in e future. Riley, 134 S. Ct. at 2489. This Court recognizes at it must take such developments into account when assessing e constitutionality of a particular search. United States v. Graham, F.3d, 2015 WL 4637931 at *13 (4 Cir. 2015). The Four Amendment must keep pace wi e inexorable march of technological progress, or its guarantees will wier and perish. United States v. Warshak, 631 F.3d 266, 285 (6 Cir. 2011). b. Quality The type of data stored on and accessible from cell phones also implicates a substantial privacy interest. As e district court explained, a forensic search of digital media reveals a class of data at raises novel privacy concerns, including files at a user had marked as deleted and location data at may provide information about activities in e home and away from e border. (JA 349.) A cell phone collects in one place many distinct types of information an address, a note, a prescription, a bank statement, a video at reveal much more in combination an any isolated record. Riley, 134 S. Ct. at 2489. Data at does not exist in e physical world exists on cell phones. Internet search history, historic location information, and apps at manage detailed information about a person s plans, interests, activities, and goals, form a revealing montage of e user s life. 14

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 24 of 70 Id. at 2490. As a result, e sum of an individual s private life can be reconstructed rough a ousand photographs labeled wi dates, locations, and descriptions. Id. The data at e government can extract from cell phones can reveal bo a comprehensive view and specific details of e individual s daily life. Graham, 2015 WL 4637931 at *11. The search here enables e government to ascertain, more or less at will, private facts about e individual, such as her political and religious beliefs, sexual habits, and so on. Id. at *10 (quoting United States v. Jones, 132 S. Ct. 945, 956 (2012) (Sotomayor, concurring)). Smart phones, like Mr. Saboonchi s, provide access to data at is not even stored on e phone itself. Riley, 134 S. Ct. at 2491. Because of cell phones ability to take advantage of cloud computing, a search of a cell phone enables e government to examine information stored in remote servers raer an on e device itself. Id. The search us defies physical boundaries. As e district court noted, cell phones also contain location data, someing Riley, as well as is Court, noted is particularly private and sensitive. Riley, 134 S. Ct. at 2490; Graham, 2015 WL 4637931 at *8. Examination of a person s historical [location data] can enable to government to trace e movements of e cell phone and its user across public and private spaces and ereby discovery e private activities and personal habits of e user. Cell phone users have an objectively 15

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 25 of 70 reasonable expectation of privacy in is information. Id. The Supreme Court described e privacy interest in cell phone data as even greater an e privacy interest in a home, which enjoys e highest Four Amendment protection. The Court explained at searching a cell phone, is far more an e most exhaustive search of a house: A phone not only contains in digital form many sensitive records previously found in e home; it also contains a broad array of private information never found in a home in any form unless e phone is. Riley, 134 S. Ct. at 2491 (emphasis in original). The search exposes not just e contents of particular files, but information about e files, which reveals a whole new category of private details. For example, a search of a physical photograph reveals only a static image. But searching a digital file of an image can reveal when and where it was taken, if it was shared wi anyone, personally identifying information about e people to whom it was sent, how it was sent, and if it was edited or deleted. Moreover, e intrusive nature of e search itself highlights e individual s privacy interest. A search of e information on a cell phone bears little resemblance to a physical search. Riley, 134 S. Ct. at 2485. The district court described e exhaustive search at occurred here. Searching data on a smart phone begins wi creating a perfect image or copy of e contents of e original device. (JA 348.) 16

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 26 of 70 Then a computer forensics expert uses specialized software to comb rough e data, often over e course of days, weeks, or even mons, searching e full contents of e imaged hard drive, examining e properties of individual files, and probing e device s unallocated slack space to reveal deleted files. (JA 348.) The process, assisted by technology, searches vast amounts of data at would exceed e capacity of a human reviewer to examine in any reasonable amount of time. Id. See also United States v. Cotterman, 709 F.3d 952, 962 (9 Cir. 2013) (describing e comprehensive and intrusive forensic examination of a laptop). A manual search of data cannot compare to a forensic search: No matter how orough or highly motivated e agent is, a manual search of a computer or digital device will never result in e human visualization of more an a fraction of e content of e device. (JA 349.) In contrast, e information available to e government after conducting a sophisticated, technology-assisted search vastly exceeds what is visible to e unassisted human examiner. This degree of invasion into a Four Amendment privacy interest necessarily impacts e factors courts must balance. See Graham, 2015 WL 4637931 at *12 ( The Four Amendment challenge is directed toward e government s investigative conduct. ). The government may not exploit evolving technology in a manner at erodes e privacy guaranteed by e Four Amendment. Kyllo v. United States, 17

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 27 of 70 533 U.S. 27, 34 (2001). Thus, e fact at e search was a comprehensive examination of all e phone s data and metadata, raer an a cursory glance at a few text messages is relevant to e Four Amendment balance. While a quick glance may not infringe upon e same level of privacy interests, e type of search here involved e maximum intrusion. Cell phones contain e privacies of life. Riley, 134 S. Ct.. at 2495. Smart phones, and all of us who use em, deserve e highest Four Amendment protections. 2. The government s interest in protecting e integrity of e border is also substantial. To be sure, e government has broad powers to advance e government s interest in preventing e entry of unwanted persons and effects... at e international border. United States v. Flores-Montano, 541 U.S. 149, 152 (2004). The government has a particularly strong interest in enforcing customs duties, preventing smuggling, and preventing inadmissible people or contraband from entering e country. United States v. Ramsey, 431 U.S. 606, 620 (1977). Travelers may be stopped in crossing an international boundary because of national self-protection reasonably requiring one entering e country to identify himself as entitled to come in, and his belongings as effects which may lawfully be 18

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 28 of 70 brought in. Carroll v. United States, 267 U.S. 132, 154 (1925). The border search exception to e Four Amendment s warrant requirement is grounded in e recognized right of e sovereign to control, subject to substantive limitations imposed by e Constitution, who and what may enter e country. Ramsey, 431 U.S. at 620. Alough e government has a heightened interest in preventing smuggling and excluding contraband or inadmissible individuals and items from entering e country, not every warrantless border search is automatically reasonable. The border search exception does not confer unfettered discretion on law enforcement. Almeida-Sanchez v. United States, 413 U.S. 266, 272-73 (1973). People who present emselves at e border are still entitled to be free from unreasonable searches and seizures. Montoya de Hernandez, 473 U.S. at 539. 3. When it comes to searching cell phone data, Riley fundamentally alters e balance between e government s interest and e individual s Four Amendment rights. Riley fundamentally changes e balance of Four Amendment interests when e government is searching e data on a cell phone. Courts cannot ignore e nature of cell phones and existing (and evolving) technology while mechanically applying legal principles at developed when a smart phone like Mr. Saboonchi s (or e Riley defendants ) were unheard of. Riley, 134 S. Ct. at 2484. Riley held at to treat a 19

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 29 of 70 cell phone search as materially indistinguishable from a search of any oer personal property is absurd. Id. at 2488 ( That is like saying a ride on horseback is materially indistinguishable from a flight to e moon. ) Riley is not limited to searches incident to arrest. The decision unequivocally addresses cell phones as a category. Id. at 2488 (emphasis added). Raer an questioning e governmental interests at stake or e assumptions underlying e warrant exception, e Court re-focused e analysis on e numerous ways at e quality and quantity of data on a cell phone change e weight of e Four Amendment interests at courts must balance. Riley s analytical framework applies to any warrant exception. The search incident to arrest does not involve its own unique balancing test. It uses e same balance at applies whenever a court considers any exception to e warrant requirement. It compared e traditionally diminished individual expectation of privacy wi e heightened governmental interest during an arrest. Id. at 2485. The Court acknowledged e government s weighty interest when searching someone incident to arrest. But considering e competing individual privacy interest in cell phone data, e balance tips toward e defendant. Riley establishes at searches of data are simply different. Certainly e principles underlying bo border searches and searches incident to arrest still exist. 20

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 30 of 70 Riley did not eliminate e search-incident-to-arrest exception, and Mr. Saboonchi does not argue at all warrantless border searches are unreasonable. Nevereless, Riley clarifies at courts cannot apply e same old analysis of traditional warrant exceptions. When it comes to searching cell phone data, a court can no longer simply recite e mantra at individuals have a diminished privacy interest at e border (or when being arrested) versus e government s heightened interest. The privacy implications of is new technology and e government s ability to infiltrate every aspect of an individual s daily life did not exist even a few years ago, let alone when e exceptions first developed. Riley recognized at e world has changed and at ose changes cannot be divorced from e Four Amendment balance. Riley controls e decision here. The search incident to arrest exception and border search exception involve comparable interests. Ramsey described e border search exception as like e similar search incident to arrest exception. 431 U.S. at 621 (citing United States v. Robinson, 414 U.S. 218, 224 (1973)). Bo exceptions are grounded in a heightened governmental interest weighed against an individual s diminished expectation of privacy. Compare Riley, 134 S. Ct. at 2488 wi Montoya de Hernandez, 473 U.S. at 539. Neier exception grants absolute, controlling weight to e government interest or scrubs e individual s interest to almost noing. Montoya de Hernandez, 473 U.S. at 539; see also Riley, 134 S. Ct. at 2484-85 21

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 31 of 70 (describing e evolution of e search incident to arrest exception and its assumption at e arrestee has a reduced expectation of privacy). The fact at a person has a diminished privacy interest does not mean at e Four Amendment falls out of e picture entirely Riley, 134 S. Ct. at 2488. To e contrary, when privacy related concerns are weighty enough a search may require a warrant, notwistanding e diminished expectations of privacy. Id. (quoting Maryland v. King, 133 S. Ct. 1958, 1979 (2013)). Riley establishes at e privacy interest here is weighty enough. Mr. Saboonchi s privacy interests are identical to ose in Riley. And e government s interests are highly analogous. Balancing e individual s privacy interest against e heightened governmental interest tilts decidedly in favor of requiring a warrant supported by probable cause. Just as in Riley, noing prevents e government from seizing e phone at e border, securing it, en applying for a search warrant. B. Because is search was e equivalent of an exhaustive search of a home, it exceeded e scope of a border search. Because is search was as intrusive as searching a home, e Four Amendment requires a warrant. The border search exception does not apply to e equivalent of searching a home. 22

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 32 of 70 In Ramsey, e Court contemplated a border search at might be deemed unreasonable because of e particularly offensive manner in which it is carried out. 431 U.S. at 618 n.13. One of e examples e Court cited involved e seizure and removal of e entire contents of a secluded cabin from a remote area in e Sierra Nevada mountains for an exhaustive search at e FBI offices 200 miles away. Kremen v. United States, 353 U.S. 346, 347-48 (1957). The Court s second example involved e warrantless and apparently unlimited search, ransacking e desk, safe, filing cases, and oer parts of e office. Go-Bart Importing Co. v. United States, 282 U.S. 344, 358 (1931). Thus, e limitless ransacking and rummaging rough e entire contents of an office or residence is so particularly offensive in manner and scope as to exemplify what constitutes an unreasonable border search. Ramsey, 431 U.S. at 618 n.13. See also Chimel v. California, 395 U.S. 752 (1969) (holding at e extensive search of an arrestee s home exceeded e scope of a search incident to arrest). And as Riley explains, e search at occurred here was tantamount to a comprehensive search of Mr. Saboonchi s home, office, and even metadata at is too hidden to independently exist in a home or office unless e phone is. Riley, 134 S. Ct. at 2491. Yet ese are e exact types searches at Ramsey identified as too offensive to qualify as a valid warrantless border search. 416 U.S. at 618. 23

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 33 of 70 The search of Mr. Saboonchi s data was strikingly similar to bo of Ramsey s examples. The government shipped his data hundreds of miles away to dissect at its leisure. That data is essentially indistinguishable from what is kept in file cabinets and desks. Moreover, e search here had an even more expansive scope an e particularly offensive examples in Ramsey because, unlike ose searches, is search was not limited by time or human perception. No byte of data or metadata was left unturned. The wholesale rummaging rough Mr. Saboonchi s data exceeds e scope of a valid border search. Not only was e search comparable to searching a home because of e type of information available from cell phones, but e search in fact allows e government to look inside a person s home. Discussing historic cell site location information, is Court stated at searching cell phone data can allow e government to place an individual and her personal property specifically, her cell phone at e person s home and oer private locations as specific points in time. Graham, 2015 WL 4637931 *9. But In e home,... all details are intimate details, because e entire area is held safe from prying government eyes. Id. (quoting Kyllo v. United States, 533 U.S. 27, 37 (2001) (ellipses and emphasis in Graham)). When e government searches a cell phone, it sees critical private detail[s] e location of a person and personal property wiin a home at a specific 24

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 34 of 70 time at e Four Amendment protect[s] from e government s intrusive use of technology. Id. Since is search allows to government to see e equivalent to e contents of Mr. Saboonchi s home and, more importantly, to learn specific details about his home, activities ere, and when he and oers are present, e government must get a warrant. C. Oer considerations also demonstrate at is search exceeded e scope of a valid warrantless border search. 1. Searches pursuant to warrant exceptions must be narrowly tailored to a specific goal. Warrantless searches based on historically recognized warrant exceptions are reasonable when ey are narrowly tailored to e purposes at gave rise to e pertinent exception. See Arizona v. Gant, 556 U.S. 332, 339 (2009) ( The scope of a search incident to arrest is commensurate wi its purposes of protecting e arresting officers and safeguarding any evidence of e offense of arrest. ). When e 7 justifications for e... exception are absent... e rule does not apply. Id. 7 See also Terry v. Ohio, 392 U.S. 1, 28-29 (1968) ( evidence may not be introduced if it was discovered by means of a seizure and search which were not reasonable related in scope to e justification for e initiation. ); Minnesota v. Dickerson, 508 U.S. 336, 373, 378 (1993) (holding at a Terry frisk was unreasonable because e officer continued exploring e suspect s pockets after concluding at e suspect was not armed, meaning at e search was unrelated to e sole justification for e search); Segura v. United States, 468 U.S. 796, 823 25

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 35 of 70 Therefore, for e border search exception to apply, e search must be narrowly tailored to e purposes behind e exception, which is to allow e sovereign to control, subject to substantive limitations imposed by e Constitution, who and what may enter e country. Ramsey, 431 U.S. at 620. The Constitution recognizes e exception because of national self-protection reasonably requiring one entering e country to identify himself as entitled to come in, and his belongs as effects which may be lawfully brought in. Carroll v. United States, 267 U.S. 132, 154 (1925). Thus, e exception applies when e search is targeted at e sovereign s right and need to protect its territorial integrity and national security. United States v. Kim, F. Supp. 2d 2015 WL 2148070 *19 (D.D.C. 2015). A search at is not linked to preventing inadmissible items, people, or contraband into e country, or collecting taxes, exceeds e scope of e exception. The border search exception allows for warrantless, suspicionless searches and us its application must remain teered to its primary purpose. United States v. Humphries, 308 Fed. Appx. 892, 896 n.1 (6 Cir. 2009). The only border searches at e Supreme Court has ever approved were (1984) ( While exigent circumstances may justify police conduct at would oerwise be unreasonable if undertaken wiout a warrant, such conduct must be strictly circumscribed by e exigencies which justify its initiation. (quoting Terry, 392 U.S. at 25-26)); United States v. Camou, 773 F.3d 932, 940 (9 Cir. 2014). 26

Appeal: 15-4111 Doc: 31 Filed: 09/03/2015 Pg: 36 of 70 specifically targeted at finding or preventing e entry into e United States of 8 contraband or inadmissible persons. Likewise, in e last twenty years, is Court has only approved border searches at are specifically targeted at e exception s 9 purposes. The only border searches at e Supreme Court or is Court have 10 approved occurred because of events at unfolded at e border, note because of law enforcement decisions made weeks before e crossing. Even searches targeted at ese goals only qualify for e warrant exception when ey occur at e border (or its functional equivalent). The exception applies to reats posed at e point of entry. Kim, 2015 WL 2148070 *19. In contrast, for 8 Carroll, 267 U.S. 132 (importing alcohol during Prohibition); Ramsey, 431 U.S. 606 (narcotics concealed in letters); United States v. 12 200-Foot Reels of Super 8mm Film, 413 U.S. 123, 125 (1973) (obscenity); United States v. Martinez-Fuerte, 428 U.S. 543 (1976) (illegal aliens); United States v. Cortez, 449 U.S. 411 (1981) (illegal aliens); Montoya de Hernandez, 473 U.S. 531 (narcotics in an alimentary canal); Flores-Montano, 541 U.S. 149 (narcotics concealed in a vehicle driving across e border). 9 United States v. Taylor, 584 Fed. Appx. 47 (4 Cir. 2014) (currency smuggling); United States v. Ickes, 393 F.3d 501 (4 Cir. 2005) (contraband child pornography); United States v. Kaczmarak, 62 Fed. Appx. 510 (4 Cir. 2003) (inadmissible alien); United States v. Switzer, 11 Fed. Appx. 65 (4 Cir. 2001) (drug smuggling); United States v. Spence, 199 F.3d 1329 (4 Cir. 1999) (currency smuggling); United States v. Aguebor, 166 F.3d 1210 (4 Cir. 1999) (alimentary canal heroin smuggler); United States v. Aragon, 155 F.3d 561 (4 Cir. 1998) (cocaine smuggling); United States v. Oriakhi, 57 F.3d 1290 (4 Cir. 1995) (currency smuggling). 10 See cases cited in notes 8 and 9. 27