Second Circuit Revisits Application of Fourth Amendment to Stored Digital Information

By Zachary Margulis-Ohnuma

The conviction of Ross Ulbricht, the mastermind behind the Silk Road marketplace on the Dark Web, has given the Second Circuit a chance to explore how to apply the Fourth Amendment to the search and seizure of stored digital information.

The government seized and searched Mr. Ulbricht’s laptop. Ulbricht, backed by the National Association of Criminal Defense Lawyers, argued on appeal that the search violated what is known as the “particularity” requirement of the Fourth Amendment. Under the Fourth Amendment, all warrants must be supported by probable cause and “particularly describ[e] the place to be searched, and the persons or things to be seized.” The Framers adopted the requirement that a warrant describe in a particular manner both the place to be searched and what the government intends to seize as evidence of a crime to prevent “general warrants.” A general warrant is a warrant that grants government agents discretion to search any and all property owned by a criminal suspect in an unrestrained and exploratory manner. By contrast, the Fourth Amendment demands that agents tell the court, before searching a suspect’s property, where they plan to search, what they plan to seize, and how the place to be searched and the things to be seized relate to the charged conduct.

Systems with digital information present special challenges for agents attempting to describe the target of their search and for courts attempting to fashion warrants that don’t authorize agents to rummage through wholly irrelevant digital files. The appeals court in U.S. v. Ulbricht recognized that hard drives typically contain a wide range of highly sensitive information, such as “tax records, diaries, personal photographs, electronic books, electronic media, and medical data, records of internet searches, [and] banking and shopping information.” Second, as a practical matter, it is difficult—if not impossible in most cases—for the government to separate sensitive, private, or irrelevant information from information that is targeted before they conduct an examination of a digital device. Often, agents must seize a suspect’s entire computer system, or gain access to a suspect’s entire email account, before they can determine if it contains evidence relevant to their investigation.

But Mr. Ulbricht and the NACDL argued that agents went too far.  The warrant to search of Ulbricht’s laptop, they maintained, violated the particularity requirement. Specifically Mr. Ulbricht and the NACDL pointed out that the warrant permitted agents to perform a cursory review of all files and folders on the device to determine relevance, and perform keyword searches through all electronic storage areas using keywords that were devised by the agents during the search, rather than articulated beforehand. According to the defense, these conditions constituted a general warrant.

The Second Circuit disagreed, finding that “it will often be impossible to identify in advance the words or phrases that will separate relevant files or documents before the search takes place, because officers cannot readily anticipate how a suspect will store information related to the charged crimes.” The court further noted that “[f]iles and documents can easily be given misleading or coded names, and words that might be expected to occur in pertinent documents can be encrypted.” By way of example, the court said that Ulbricht kept records of drug trafficking related conversations in a folder labeled “mbsobzvkhwx4hmjt.”

Although the court admitted that the warrant was very broad, granting agents wide latitude to search every file and folder on the computer’s digital file system, it found that the unique aspects of the case justified the grant of power. Ulbricht was charged with directing a vast drug distribution conspiracy almost entirely from his personal computer. As a result, that device likely contained extensive evidence of the conspiracy in many varied forms, and in many different locations. Further, the technological sophistication of the Silk Road led agents to reasonably believe that Ulbricht would take steps to hide or obscure his involvement, thus justifying a thorough search of his devices for hidden evidence. The court concluded that although the warrant was broad, it was particular enough in light of the central role Ulbricht’s digital devices played in the charged conduct and the inherent difficulties of discovering relevant evidence that would likely be hidden by a tech-savvy defendant like Mr. Ulbricht.

The decision suggests future challenges to warrants that grant government agents wide authority to search digital devices. Although the court endorsed a broad warrant in this case, the court stated that it was “sensitive to the difficulties associated with preserving a criminal defendant’s privacy while searching through his electronic data and computer hard drives” and that “[a] future case may require this court to articulate special limitations on digital searches.”

In challenging broad digital warrants, defense attorneys should evaluate the types of documents or files the government is permitted to search in light of the charged conduct – for example, it may make little sense for the government to review video files on a defendant’s computer in the course of an investigation into tax fraud. Defense lawyers should also consider whether the target of the search is technologically sophisticated and may take steps to hide digital evidence, whether the place to be searched is shared by others not under investigation, and whether the charged conduct typically results in extensive digital records that will likely be found in the place to be searched.