United States v. Warshak

BOGGS, J., delivered the opinion of the court, in which McKEAGUE, J., joined. KEITH, J. (pp. 333-36), delivered a separate opinion concurring in the result.

OPINION

Berkeley Premium Nutraceuticals, Inc., was an incredibly profitable company that served as the distributor of Enzyte, an herbal supplement purported to enhance male sexual performance. In this appeal, defendants Steven Warshak (“Warshak”), Harriet Warshak (“Harriet”), and TCI Media, Inc. (“TCI”), challenge their convictions stemming from a massive scheme to defraud Berkeley’s customers. Warshak and Harriet also challenge their sentences, as well as two forfeiture judgments.

Given the volume and complexity of the issues presented, we provide the following summary of our holdings:

(1) Warshak enjoyed a reasonable expectation of privacy in his emails vis-a-vis NuVox, his Internet Service Provider. See Katz v. United States, 389 U.S. 347, 88 S.Ct. 507, 19 L.Ed.2d 576 (1967). Thus, government agents violated his Fourth Amendment rights by compelling NuVox to turn over the emails without first obtaining a warrant based on probable cause. However, because the agents relied in good faith on provisions of the Stored Communications Act, the exclusionary rule does not apply in this instance. See Illinois v. Krull, 480 U.S. 340, 107 S.Ct. 1160, 94 L.Ed.2d 364 (1987).

(2) The district court did not err in refusing to hold a full-fledged hearing under Kastigar v. United States, 406 U.S. 441, 92 S.Ct. 1653, 32 L.Ed.2d 212 (1972), when determining whether government agents had improperly used privileged materials seized during a valid search of Berkeley’s headquarters. Kastigar does not apply with full force outside the context of compelled testimony. See United States v. Squillacote, 221 F.3d 542 (4th Cir.2000).

(3) The district court did not abuse its discretion by failing to order the government to provide discovery in a different format, as Federal Rule of Criminal Procedure 16 is silent on the issue of the form that discovery must take. Moreover, the government did not duck its obligations under Brady v. Maryland, 373 U.S. 83, 83 S.Ct. 1194, 10 L.Ed.2d 215 (1963), by providing the defendants with massive quantities of discovery. See United States v. Skilling, 554 F.3d 529 (5th Cir.2009), vacated in part on other grounds, — U.S. -, 130 S.Ct. 2896, 177 L.Ed.2d 619 (2010). Finally, the district court did not err in refusing to grant the defendants a continuance so that they could continue examining the discovery materials turned over by the government.

(4) The district court did not err in refusing to grant Warshak a new trial based on an alleged Brady violation, as the purportedly exculpatory material did not rise *275to the level of materiality. See Kyles v. Whitley, 514 U.S. 419, 115 S.Ct. 1555, 131 L.Ed.2d 490 (1995).

(5) The district court did not err in refusing to grant the defendants a new trial on the basis of prosecutorial misconduct. Though the prosecution did make a number of improper remarks during its rebuttal argument, the remarks were not flagrant. See United States v. Carter, 236 F.3d 777 (6th Cir.2001).

(6) The evidence was sufficient to support Warshak’s and Harriet’s respective convictions for conspiracy to commit mail, wire, and bank fraud, in violation of 18 U.S.C. § 1349. See Jackson v. Virginia, 443 U.S. 307, 99 S.Ct. 2781, 61 L.Ed.2d 560 (1979). Those convictions are therefore sustained.

(7) The evidence was sufficient to support Warshak’s convictions for mail fraud, in violation of 18 U.S.C. § 1341. Those convictions are therefore sustained.

(8) The evidence was sufficient to support Warshak’s and Harriet’s respective convictions for bank fraud, in violation of 18 U.S.C. § 1344. Furthermore, the district court did not err in instructing the jury that, under certain circumstances, the government may prove specific intent to defraud a bank by showing specific intent to defraud a third party. See United States v. Reaume, 338 F.3d 577 (6th Cir.2003). Those convictions are therefore sustained.

(9) The evidence was sufficient to support Warshak’s conviction for conspiracy to commit access-device fraud, in violation of 18 U.S.C. § 1029. That conviction is sustained.

(10) The evidence was sufficient to support Warshak’s and TCI’s respective convictions for money laundering, in violation of 18 U.S.C. §§ 1956, 1957. Those convictions are affirmed. By contrast, the evidence was insufficient to support Harriet’s money-laundering convictions. Those convictions are therefore reversed.

(11) The evidence was sufficient to support Warshak’s conviction for conspiracy to obstruct an FTC proceeding, in violation of 18 U.S.C. §§ 371, 1505. As a consequence, that conviction is sustained.

(12) The district court did not err in refusing to order the government to reveal whether or not it had conducted any additional surreptitious searches of Warshak’s emails or communications. The discovery afforded by Federal Rule of Criminal Procedure 16 is limited to the evidence referred to in its express provisions, United States v. Presser, 844 F.2d 1275, 1285 (6th Cir.1988), and those provisions do not encompass the information sought by the defendants.

(13) The district court failed to provide an adequate explanation of its determination that the defendants should be held accountable for $411 million in losses. See Fed.R.Crim.P. 32(i)(3)(B); United States v. White, 492 F.3d 380, 415 (6th Cir.2007). We therefore vacate Warshak’s sentence and remand.

(14) The district court did not abuse its discretion in refusing to admit certain evidence during the forfeiture phase of the trial. Furthermore, the evidence was sufficient to support the proceeds-money and money-laundering forfeiture judgments against Warshak. In addition, the evidence was sufficient to support the proceeds-money forfeiture judgment against Harriet, but it was insufficient to support the money-laundering forfeiture judgment against her. Therefore, the proceeds-money forfeiture judgment is affirmed with respect to both Warshak and Harriet, and the money-laundering money judgment is affirmed with respect to Warshak, but reversed with respect to Harriet.

*276I. STATEMENT OF THE FACTS

A. Factual Background

In 2001, Steven Warshak (“Warshak”) owned and operated a number of small businesses in the Cincinnati area. One of his businesses was TCI Media, Inc. (“TCI”), which sold advertisements in sporting venues. Warshak also owned a handful of companies that offered a modest line of so-called “nutraceuticals,” or herbal supplements.1 While the companies bore different names and sold different products, they appear to have been run as a single business, and they were later aggregated to form Berkeley Premium Nutraceuticals, Inc. (“Berkeley”).2 In Berkeley’s early days, the company’s workforce was relatively minute; the company employed approximately 12 to 15 people, nearly all of whom were Warshak’s friends and family. Among them was his mother, Harriet Warshak (“Harriet”), who processed credit-card payments.

As the company grew, Warshak brought on additional employees to facilitate expansion, but he remained extremely “hands-on” with respect to the company’s operations. In 2001, he hired James Teegarden, who eventually became Berkeley’s Chief Operating Officer. Warshak also hired Shelley Kinmon to oversee the company’s sales, later elevating her to the role of Vice-President. In 2002, Sue and Greg Cossman, Warshak’s sister and brother-in-law, joined the company. Sue worked in Customer Care, where she dealt with customer complaints. Greg came in as the President of the company and thereafter functioned in various other capacities. That year also saw the hiring of Sam Grote, who was brought on board to work in the marketing department.

To sell its products, Berkeley took orders over the phone, but it also made sales through the mail and over the Internet. Customers purchased products with their credit cards, and their credit-card numbers were entered into a database along with other information. During sales calls, representatives would read from sales scripts,3 which listed the major points to cover during the transaction. Shelley Kinmon testified that Warshak had the final word on the content of the scripts. Often, the scripts would include a description of the desired product, as well as language intended to persuade more pliant customers to make additional purchases.

In the latter half of 2001, Berkeley launched Enzyte, its flagship product. At the time of its launch, Enzyte was purported to increase the size of a man’s erection. The product proved tremendously popular, and business rose sharply. By 2004, demand for Berkeley’s products had grown so dramatically that the company employed 1500 people, and the call center remained open throughout the night, taking orders at breakneck speed. Berkeley’s line of supplements also expanded, ballooning from approximately four products to around thirteen. By year’s end, Berkeley’s annual sales topped out at around $250 million, largely on the strength of Enzyte.

*2771. Advertising

The popularity of Enzyte appears to have been due in large part to Berkeley’s aggressive advertising campaigns. The vast majority of the advertising — approximately 98% — was conducted through television spots. Around 2004, network television was saturated with Enzyte advertisements featuring a character called “Smilin’ Bob,” whose trademark exaggerated smile was presumably the result of Enzyte’s efficacy. The “Smilin’ Bob” commercials were rife with innuendo and implied that users of Enzyte would become the envy of the neighborhood.

In addition to the television commercials, however, there were also advertisements in other media, such as print and radio. In 2001, just after Enzyte’s premiere, advertisements appeared in a number of men’s interest magazines. At Warshak’s direction, those advertisements cited a 2001 independent customer study, which purported to show that, over a three-month period, 100 English-speaking men who took Enzyte experienced a 12 to 31% increase in the size of their penises. The 2001 study was also referenced in radio advertisements and appeared on the company’s website, as well as in brochures and sales calls. James Teegarden later testified that the survey was bogus. He stated that, prior to the appearance of the advertisements, Warshak instructed him to create a spreadsheet and to fill it with fabricated data. Teegarden testified that he plucked the numbers out of the air and generated the spreadsheet over a twenty-four hour period.

A number of advertisements also indicated that Enzyte boasted a 96% customer satisfaction rating. Teegarden testified that that statistic, too, was totally spurious. Before the claim began showing up in Berkeley’s literature, Warshak had asked him to harvest 500 names from the customer database and to “mark an ‘X’ by either satisfied or very satisfied on say 475 of those.” As for the remaining 25, Tee-garden “was to put not satisfied.” Thereafter, the customer-satisfaction statistic cropped up in Berkeley’s print advertisements and in the “sales pitches, brochures, [and on the] Internet.”

Finally, numerous print and radio advertisements boasted that Enzyte was the brainchild of reputable doctors with impressive educational pedigrees. According to the ads, “Enzyte was developed by Dr. Fredrick Thomkins, a physician with a biology degree from Stanford and Dr. Michael Moore, a leading urologist from Harvard.” The ads also stated that the doctors had collaborated for thirteen years in developing a supplement designed to “stretch and elongate.” In reality, the doctors were just as fictitious as “Smilin’ Bob.” Investigators who contacted Stanford and Harvard learned that neither man existed.

2. The Auto-Ship Program

The “life blood” of the business was its auto-ship program, which was instituted in 2001, shortly before Enzyte hit the market.4 The auto-ship program was a continuity or negative-option program, in which a customer would order a free trial of a product and then continue to receive additional shipments of that product until he opted out. Before each new continuity shipment arrived on the customer’s doorstep, a corresponding charge would appear on his credit-card statement. The shipments and charges would continue until the customer decided to withdraw from the *278program, which required the customer to notify the company.

In the early days of the auto-ship program, customers who ordered products over the phone were not told that they were being enrolled.5 From August 2001 to at least the end of December 2002,6 customers were simply added to the program at the time of the initial sale without any indication that they would be on the hook for additional charges. Apparently, products were shipped with literature explaining the program, but no authorization was sought in advance of the shipment. According to Teegarden, Warshak explained that the auto-ship program was never mentioned because “nobody would sign up.” If nobody signed up, “you couldn’t make revenue.”

This policy resulted in a substantial volume of complaints, both to Berkeley and to outside organizations. In October 2002, the Better Business Bureau (“BBB”) contacted Berkeley and indicated that more than 1,500 customers had called to voice their consternation. Because of the complaints, Berkeley’s sales scripts and website began to include some language disclosing the auto-ship program.7 A number of internal emails indicate that sales representatives were required to read the disclosure language and faced punishment if they failed to do so. To monitor the interactions between representatives and customers, Berkeley installed a recording system for all incoming calls.

However, as a number of Berkeley insiders testified, the compulsory disclosure language was not always read, and it was designed not to work. Shelley Kinmon testified that the disclosure of the continuity shipments was only made after the customer had placed his order. In other words, the sales representative had already taken the customer’s credit-card information when auto-ship was mentioned. Also, the disclosures were deliberately made with haste, and they were placed after unrelated language that was intended to divert or deaden the customer’s attention. In the case of Enzyte, sales reps were instructed to lead into the disclosure language by stating that “the product is not a contraceptive nor will it prevent or treat any sexually transmitted disease.”8 According to Teegarden, the thinking was that, “if we started off with a statement about a contraceptive, something other than what it was, that people wouldn’t really listen to what we were disclosing to them.”

*279Moreover, disclosure of the auto-ship program was sometimes irrelevant. For example, in November 2003, Berkeley hired a company called West to handle “sales calls that were from ... Avlimil or Enzyte advertisements.” During the calls, West’s representatives asked customers if they wanted to be enrolled in the auto-ship program, and over 80% of customers declined. When Warshak learned what was happening, he issued instructions to “take those customers, even if they decline[d], even if they said no to the Auto-Ship program, go ahead and put them on the Auto-Ship program.” A subsequent email between Berkeley employees indicated that “all [West] customers, whether they know it or not, are going on [auto-ship].” As a result, numerous telephone orders resulted in unauthorized continuity shipments.

However, not all of Berkeley’s auto-ship issues related to the telephone. Many Berkeley sales were the result of orders placed on the Internet, where disclosure of the auto-ship program was inconsistent. In 2001, when Berkeley was in its infancy, the company’s websites contained no indication that customers would be enrolled in the program. Thereafter, disclosures were placed on the websites, but the disclosures would “appear[ ], disappear[ ], and chang[e].” In 2003, for instance, disclosure language that had been added to Berkeley’s Avlimil website was removed because sales had been “drastically affected.” Additionally, the language that did appear was often confusing and contained non sequiturs.

By July 2004, the complaints arising from Berkeley’s auto-ship program had not slowed, so the President of the BBB reached out to Berkeley, sending a letter directly to Warshak. The purpose of the letter was to express “serious concerns about the number of complaints that [the BBB] had received.” The complaints “related to a single issue, which was the [auto-ship] program.” According to the President of the BBB, the organization “had asked on numerous occasions that [Berkeley] consider dropping [the program], and got no positive response.”

3. The Merchant Banks

In order for Berkeley’s business to operate, it was essential that the company be able to accept credit cards as a form of payment.9 To process credit-card transactions, Berkeley obtained lines of credit from several merchant banks. The relationships between Berkeley and the merchant banks involved intermediaries known as credit-card processors. Often, the processors had contractual agreements with the merchant banks, and the processors were the ones who set up the credit-card processing arrangements with Berkeley. Nonetheless, when Berkeley applied for a merchant account with a given processor, the applications were passed along to the banks. Furthermore, either the banks or the processors could terminate Berkeley’s merchant accounts.

In early 2002, Warshak’s merchant account at the Bank of Kentucky was terminated for excessive “chargebacks.” A chargeback occurs when a customer calls the credit card company directly and contests or disputes a charge. Merchant banks — and credit-card processors — will generally not do business with merchants that experience high volumes of charge-backs, as those merchants present a greater financial risk. In determining whether *280a merchant is experiencing excessive chargebacks, the banks refer to a figure known as the chargeback ratio, which is simply the percentage of transactions in a given 30-day period that result in a chargeback. For example, if a company conducts 100 credit-card transactions and one chargeback results, the company will have a chargeback ratio of 1%. Typically, if a merchant experiences more than one chargeback per hundred transactions, its chargeback ratio is deemed too high, resulting in fines and, eventually, termination of its accounts, either by the merchant bank or the credit-card processor.

Following the termination of the merchant account at the Bank of Kentucky, the company applied for merchant accounts with a number of other banks. In some instances, the applications, which often bore Harriet’s signature, falsely listed her as the CEO and 100% owner of the company. In other instances, Warshak would complete the applications in his own name but falsely claim that he had never had a merchant account terminated. These prevarications were included in the applications because the prior termination would likely diminish Berkeley’s chances of securing the services of other processors.

Despite its history with the Bank of Kentucky, Berkeley was able to land (or retain) merchant accounts with several processors. However, due to the auto-ship program and an extremely onerous refund policy,10 Berkeley was repeatedly at risk of crossing the critical 1% chargeback threshold.11 At company meetings, the chargeback ratio was a frequent topic of discussion, as was the possibility that Berkeley’s accounts would be terminated. To prevent that from happening, a number of strategies were devised to artificially inflate the number of sales transactions and thus the denominator of the charge-back ratio, reducing that crucial ratio. One strategy was called “double-dinging.” That practice involved splitting a single transaction into two, thereby driving up the number of transactions and diminishing the chargeback ratio. A double-ding might entail carving a $59.95 charge into a $54.95 charge for the product itself and a $5.00 charge for shipping. Warshak directed that virtually all sales be double-dinged, and by 2003, triple-dinging was initiated.

Another way the company depressed the chargeback ratio was to make numerous charges to Warshak’s personal credit cards. At Warshak’s behest, Berkeley employees would ring up $1.00 charges on each of his credit cards until their limits were reached. Apparently, the thinking *281was that this torrent of additional transactions would dilute the number of charge-backs and keep the ratio under 1%. The same thinking led the company to charge and then refund the credit cards of randomly selected customers. The charges were made without authorization, and if anyone complained about the odd activity on his card, he was told that it was the result of a computer glitch. Through the use of these techniques and others, the company was able to stave off termination of its merchant-bank accounts.

B. Procedural History

In September 2006, a grand jury sitting-in the Southern District of Ohio returned a 112-count indictment charging Warshak, Harriet, TCI, and several others with various crimes related to Berkeley’s business. Warshak was charged with conspiracy to commit mail, wire, and bank fraud (Count 1); mail fraud (Counts 2-13); making false statements to banks (Counts 14,16-22, 24-26, 28); bank fraud (Counts 15, 23, 27); conspiracy to commit and attempt to commit access-device fraud (Count 29); conspiracy to commit money laundering (Count 34); money laundering (Counts 32-98, 102-106, 108); conspiracy to commit misbranding (Count 109); misbranding (Count 110); and, lastly, conspiracy to obstruct a Federal Trade Commission (“FTC”) proceeding (Count 112). Harriet was charged with conspiracy to commit mail, wire, and bank fraud (Count 1); bank fraud (Count 27); making false statements to a bank (Count 28); conspiracy to commit money laundering (Counts 30-31); and money laundering (Counts 99-101, 107). TCI was charged with money laundering (Counts 57-58, 60-73, 79, 83, 91-93).

Before trial, numerous motions were filed. First, Warshak moved to exclude thousands of emails that the government obtained from his Internet Service Providers. That motion was denied. Warshak also moved to bar the government from using any evidence “derived through improper access to privileged attorney-client communications.” Appellant’s Br. at 42. Following a “Kastigar-like” evidentiary hearing at which governmental inspectors testified that they did not make use of any privileged materials, the district court denied the motion. In addition, the defendants requested a continuance, which was denied.

Over fifteen months later, in January 2008, the case proceeded to trial. Approximately six weeks later, the trial ended and the defendants were convicted of the majority of the charges. Warshak was acquitted of Counts 14-22, 24-26, and 28, which charged him with making false statements to banks, and he was also acquitted of Counts 109-110, which charged him with misbranding offenses. Harriet was acquitted of Count 28, which alleged that she made false statements to a bank. She was convicted on Counts 27, 30-31, 99-101, and 107.

As soon as the trial was over, a forfeiture hearing was held, during which the jury heard additional evidence. At the hearing, the defendants attempted to introduce certain evidence that many of Berkeley’s sales were legitimate, but the district court ruled that the evidence was irrelevant. When the hearing concluded, the jury found that the government had established the requisite nexus between certain assets and the crimes of both fraud and money laundering.

On August 27, 2008, the defendants were sentenced. Warshak received a sentence of 25 years of imprisonment. He was also ordered to pay a fine of $93,000 and a special assessment of $9,300. In addition, he was ordered to surrender $459,540,000 in proceeds-money-judgment forfeiture and $44,876,781.68 in money-laundering-*282judgment forfeiture. Harriet was sentenced to 24 months of imprisonment, ordered to pay a special assessment of $800, and held jointly and severally liable for the forfeiture judgments. TCI was sentenced to five years of probation and ordered to pay a fine of $160,000 and a special assessment of $6,400.

Following a series of unsuccessful post-trial motions, the defendants timely appealed.

II. ANALYSIS

A. The Search & Seizure of Warshak’s Emails

Warshak argues that the government’s warrantless, ex parte seizure of approximately 27,000 of his private emails constituted a violation of the Fourth Amendment’s prohibition on unreasonable searches and seizures.12 The government counters that, even if government agents violated the Fourth Amendment in obtaining the emails, they relied in good faith on the Stored Communications Act (“SCA”), 18 U.S.C. §§ 2701 et seq., a statute that allows the government to obtain certain electronic communications without procuring a warrant. The government also argues that any hypothetical Fourth Amendment violation was harmless. We find that the government did violate Warshak’s Fourth Amendment rights by compelling his Internet Service Provider (“ISP”) to turn over the contents of his emails. However, we agree that agents relied on the SCA in good faith, and therefore hold that reversal is unwarranted.13

1. The Stored Communications Act

The Stored Communications Act (“SCA”), 18 U.S.C. §§ 2701 et seq., “permits a ‘governmental entity’ to compel a service provider to disclose the contents of [electronic] communications in certain circumstances.” Warshak II, 532 F.3d at 523. As this court explained in Warshak II:

Three relevant definitions bear on the meaning of the compelled-diselosure provisions of the Act. “[Electronic communication service[s]” permit “users ... to send or receive wire or electronic communications,” [18 U.S.C.] § 2510(15), a definition that covers basic e-mail services, see Patricia L. Bellia et ah, Cyberlaw: Problems of Policy and Jurisprudence in the Information Age 584 (2d ed. 2004). “[Electronic storage” is “any temporary, intermediate storage of a wire or electronic communication ... and ... any storage of such communication by an electronic communication ser*283vice for purposes of backup protection of such communication.” 18 U.S.C. § 2510(17). “[RJemote computing serviced” provide “computer storage or processing services” to customers, id. § 2711(2), and are designed for longer-term storage, see Orín S. Kerr, A User’s Guide to the Stored Communications Act, and a Legislator’s Guide to Amending It, 72 Geo. Wash. L.Rev. 1208, 1216 (2004).

The compelled-disclosure provisions give different levels of privacy protection based on whether the e-mail is held with an electronic communication service or a remote computing service and based on how long the e-mail has been in electronic storage. The government may obtain the contents of e-mails that are “in electronic storage” with an electronic communication service for 180 days or less “only pursuant to a warrant.” 18 U.S.C. § 2703(a). The government has three options for obtaining communications stored with a remote computing service and communications that have been in electronic storage with an electronic service provider for more than 180 days: (1) obtain a warrant; (2) use an administrative subpoena; or (3) obtain a court order under § 2703(d). Id. § 2703(a), (b).

532 F.3d at 523-24 (some alterations in original).

2. Factual Background

Email was a critical form of communication among Berkeley personnel. As a consequence, Warshak had a number of email accounts with various ISPs, including an account with NuVox Communications. In October 2004, the government formally requested that NuVox prospectively preserve the contents of any emails to or from Warshak’s email account. The request was made pursuant to 18 U.S.C. § 2703(f) and it instructed NuVox to preserve all future messages.14 NuVox acceded to the government’s request and began preserving copies of Warshak’s incoming and outgoing emails — copies that would not have existed absent the prospective preservation request. Per the government’s instructions, Warshak was not informed that his messages were being archived.

In January 2005, the government obtained a subpoena under § 2703(b) and compelled NuVox to turn over the emails that it had begun preserving the previous year. In May 2005, the government served NuVox with an ex parte court order under § 2703(d) that required NuVox to surrender any additional email messages in Warshak’s account. In all, the government compelled NuVox to reveal the contents of approximately 27,000 emails. Warshak did not receive notice of either the subpoena or the order until May 2006.

3. The Fourth Amendment

The Fourth Amendment provides that “[t]he right of the people to be secure in their persons, houses, papers, and effects, against unreasonable searches and seizures, shall not be violated, and no Warrants shall issue, but upon probable cause.... ” U.S. Const, amend. IV. The fundamental purpose of the Fourth Amendment “is to safeguard the privacy and security of individuals against arbitrary invasions by government officials.” Camara v. Mun. Ct., 387 U.S. 523, 528, 87 S.Ct. 1727, 18 L.Ed.2d 930 (1967); see Skinner v. Ry. Labor Execs.’ Ass’n, 489 U.S. 602, 613-14, 109 S.Ct. 1402, 103 L.Ed.2d 639 (1989) (“The [Fourth] Amend*284ment guarantees the privacy, dignity, and security of persons against certain arbitrary and invasive acts by officers of the Government or those acting at their direction.”).

Not all government actions are invasive enough to implicate the Fourth Amendment. “The Fourth Amendment’s protections hinge on the occurrence of a ‘search,’ a legal term of art whose history is riddled with complexity.” Widgren v. Maple Grove Twp., 429 F.3d 575, 578 (6th Cir.2005). A “search” occurs when the government infringes upon “an expectation of privacy that society is prepared to consider reasonable.” United States v. Jacobsen, 466 U.S. 109, 113, 104 S.Ct. 1652, 80 L.Ed.2d 85 (1984). This standard breaks down into two discrete inquiries: “first, has the [target of the investigation] manifested a subjective expectation of privacy in the object of the challenged search? Second, is society willing to recognize that expectation as reasonable?” California v. Ciraolo, 476 U.S. 207, 211, 106 S.Ct. 1809, 90 L.Ed.2d 210 (1986) (citing Smith v. Maryland, 442 U.S. 735, 740, 99 S.Ct. 2577, 61 L.Ed.2d 220 (1979)).

Turning first to the subjective component of the test, we find that Warshak plainly manifested an expectation that his emails would be shielded from outside scrutiny. As he notes in his brief, his “entire business and personal life was contained within the ... emails seized.” Appellant’s Br. at 39-40. Given the often sensitive and sometimes damning substance of his emails,15 we think it highly unlikely that Warshak expected them to be made public, for people seldom unfurl their dirty laundry in plain view. See, e.g., United States v. Maxwell, 45 M.J. 406, 417 (C.A.A.F.1996) (“[T]he tenor and content of e-mail conversations between appellant and his correspondent, ‘Launehboy,’ reveal a[n] ... expectation that the conversations were private.”). Therefore, we conclude that Warshak had a subjective expectation of privacy in the contents of his emails.

The next question is whether society is prepared to recognize that expectation as reasonable. See Smith, 442 U.S. at 740, 99 S.Ct. 2577. This question is one of grave import and enduring consequence, given the prominent role that email has assumed in modern communication. Cf. Katz, 389 U.S. at 352, 88 S.Ct. 507 (suggesting that the Constitution must be read to account for “the vital role that the public telephone has come to play in private communication”). Since the advent of email, the telephone call and the letter have waned in importance, and an explosion of Internet-based communication has taken place. People are now able to send sensitive and intimate information, instantaneously, to friends, family, and colleagues half a world away. Lovers exchange sweet nothings, and businessmen swap ambitious plans, all with the click of a mouse button. Commerce has also taken hold in email. Online purchases are often documented in email accounts, and email is frequently used to remind patients and clients of imminent appointments. In short, “account” is an apt word for the conglomeration of stored messages that comprises an email account, as it provides an account of its owner’s life. By obtaining access to someone’s email, government agents gain the ability to peer deeply into his activities. Much hinges, therefore, on whether the government is permitted to request that a commercial ISP turn over the contents of a subscriber’s emails without triggering the machinery of the Fourth Amendment.

*285In confronting this question, we take note of two bedrock principles. First, the very fact that information is being passed through a communications network is a paramount Fourth Amendment consideration. See ibid.; United States v. U.S. Dist. Court, 407 U.S. 297, 313, 92 S.Ct. 2125, 32 L.Ed.2d 752 (1972) (“[T]he broad and unsuspected governmental incursions into conversational privacy which electronic surveillance entails necessitate the application of Fourth Amendment safeguards.”). Second, the Fourth Amendment must keep pace with the inexorable march of technological progress, or its guarantees will wither and perish. See Kyllo v. United States, 533 U.S. 27, 34, 121 S.Ct. 2038, 150 L.Ed.2d 94 (2001) (noting that evolving technology must not be permitted to “erode the privacy guaranteed by the Fourth Amendment”); see also Orín S. Kerr, Applying the Fourth Amendment to the Internet: A General Approach, 62 Stan. L.Rev. 1005, 1007 (2010) (arguing that “the differences between the facts of physical space and the facts of the Internet require courts to identify new Fourth Amendment distinctions to maintain the function of Fourth Amendment rules in an online environment”).

With those principles in mind, we begin our analysis by considering the manner in which the Fourth Amendment protects traditional forms of communication. In Katz, the Supreme Court was asked to determine how the Fourth Amendment applied in the context of the telephone. There, government agents had affixed an electronic listening device to the exterior of a public phone booth, and had used the device to intercept and record several phone conversations. See 389 U.S. at 348, 88 S.Ct. 507. The Supreme Court held that this constituted a search under the Fourth Amendment, see id. at 353, 88 S.Ct. 507, notwithstanding the fact that the telephone company had the capacity to monitor and record the calls, see Smith, 442 U.S. at 746-47, 99 S.Ct. 2577 (Stewart, J., dissenting). In the eyes of the Court, the caller was “surely entitled to assume that the words he utter[ed] into the mouthpiece w[ould] not be broadcast to the world.” Katz, 389 U.S. at 352, 88 S.Ct. 507. The Court’s holding in Katz has since come to stand for the broad proposition that, in many contexts, the government infringes a reasonable expectation of privacy when it surreptitiously intercepts a telephone call through electronic means. Smith,