The Evolution of Wiretapping

The Internet is a means, essentially, of transmitting
information across large distances at a ridiculously rapid pace. All of the various
types of attacks and intrusions that have become commonplace on the Internet
today are, fundamentally, based upon the ability to corrupt the flow of
accurate information—whether by stealing a portion of it for misuse, disrupting
the flow so that accurate information does not arrive in a timely manner, or
inserting false information into an otherwise secure stream of data. If the
confidentiality and integrity of the information being transmitted cannot be
relied upon, then the system or network that acts based upon that data is
vulnerable. That, in a nutshell, is the core of much of cyber warfare, cyber
crime, and cyber espionage—the ability to destroy or corrupt the flow of
information from your enemies through intrusion or attack—and the collateral
real-world effects of that destruction.

What if you could make your data incorruptible (or,
slightly less useful but almost as good, if you could make your data
tamper-evident, so that any corruption or interception was known to you)? If
your goal is to protect your own information from attack, there are a number of
ways you might achieve that objective. One of the earliest defensive measures
taken in cyberspace was a method as old as human history—data and information
were protected by encryption.

But this expansion of cryptographic capabilities to
protect cyber networks comes with an uncertain cost to order and governance. Advances
in cryptographic technology have made it increasingly difficult for individuals
to “crack” a code. Code breaking is as old as code making, naturally. But as
the run of technology has played out encryption increasingly has an advantage
over decryption, and recent advances have brought us to the point where
decryption can, in some cases, be effectively impossible. This has the positive
benefit of allowing legitimate users to protect their lawful secrets—but it has
the inevitable effect of distributing a technology that can protect malevolent
uses of the Internet. If the United States government can encrypt its data, so
can China, or the Russian mob, or a Mexican drug cartel.

An alternative strategy that works in concert with
encryption is to make your information transmission immune to interception. Here,
too, the changes wrought by Internet technology have made interception more
difficult and enhanced the security of communications. In the world of
telephone communications, for example, intercepting a communication was as
simple as attaching two alligator clips to the right wire—hence the word
“wiretapping.” Communications through the Internet are wholly different: the information
being transmitted is broken up into small “packets” that are separately
transmitted along different routes and then reassembled when they arrive at
their destination. This disassembly of the data makes effective interception
appreciably more difficult.

These two technological developments have led to
controversy over critical policy issues that bear on cyber conflicts today. In
the wiretapping realm, can the government require communications transmission
companies to assure the government access to communications? In other words, can
they require internet service providers (ISPs) to provide them access to the
data as it transits the net?

And if they can, under what rules would these communications
be accessed? At the whim of a government? Or only with an appropriate court
order? Under what sorts of standards?

I. Wiretapping
– Yesterday and Today

Communications Systems



Google Chat

Google Apps


Quick Connect




My Space

Second Life

EVE Online

Chat Anywhere




Pre-Internet, wiretapping was an easy physical task. Early telephony
worked by connecting two people who wished to communicate through a single,
continuous wire (typically made of copper). The image that captures this
concept most readily is of a telephone operator moving plugs around on a board
and, by that effort, physically establishing an end-to-end wire connection
between the two speakers.

That made wiretapping easy. All that was required was
attaching a wire to a terminal post and then hooking the connection up to a
tape recorder. The interception didn’t even need to be made at the central
Publicly Switched Telephone Network (PSTN) switching station. Any place on the
line would do. And, there was only one telephone company, AT&T, and only
one system, so coordination with the PSTN was easy if it was authorized.

Things became a little more complicated when AT&T
broke up into the “Baby Bells,” but the real challenge came with the
development of new communications technologies. As microwave, FM, and fiber
optic technologies were introduced, the technical challenges of intercepting
communications increased as well.[3] The
technological difficulty in intercepting communications grew exponentially in a
relatively short period of time.

Today the problem is
even more complex—in addition to cellular telephones, we now have instant
messaging and email and text messaging for written communications. If you want
to communicate by voice, you can use Skype (a web-based video conferencing
system), or Google Chat (an embedded browser-based chat program). Businesses
use web-teleconference tools for teleconferences, and many people (particularly
in the younger generation) communicate while present in virtual worlds through their
“avatars.” Twitter and Facebook allow instant communication between large
groups of people.

In short, we have created an almost infinite number of
ways in which one can communicate.[4] When
combined with the packet-switching nature of Internet web transmissions, and
the development of peer-to-peer networks (that completely do away with
centralized servers), the centralized PSTN network has become a dodo. And the
Internet Engineering Task Force (the organization that sets standards for
operation of the internet) has rejected requests to mandate an interception
capability within the architecture of the internet communications protocols.[5] With
these changes, the laws and policies for authorized wiretapping have, effectively,
become obsolete.

II. Wiretapping
and Changing Technology

The law enforcement and intelligence communities face
two challenges in administering wiretap laws in the age of the Internet—one of
law and one of technology. The legal issue is relatively benign and, in some
ways, unencumbered by technical complexity, though highly controversial
nonetheless. We need a series of laws that define when and under what
circumstances the government may lawfully intercept a communication. For the
most part the authorization issues are ones involving the updating of existing
authorities to apply explicitly to new technologies. The technical issue is far
harder to solve—precisely how can the desired wiretap be achieved?

Legal Authorization—In
Katz v. United States,[6] the Supreme Court held that the Fourth Amendment applied to electronic
communications, and that a warrant was required for law enforcement-related
electronic surveillance conducted in the United States. Katz was codified in the Omnibus Crime Control and Safe Streets Act
of 1968, with particular requirements for such interceptions laid down in Title
III.[7] In
general, Title III prohibits the interception of “wire, oral, or electronic
communications” by government agencies without a warrant and regulates the disclosure
and use of authorized intercepted communications by investigative and law
enforcement officers.

Reflecting its pre-Internet origins, Title III
originally covered only “wire” and “oral” communication. It has since been
modified to take account of technological changes and now covers all forms of
electronic communication (including, for example, e-mails). [8] The law also regulates the use of “pen register” and “trap and trace”
devices (that is, devices designed to capture the “addressing information” of a
call, such as the dialing information of incoming and outgoing phone calls). In
general, this “non-content” information may be collected without a warrant or
showing of probable cause, unlike the “content” portions of a message.

As a core part
of its structure, Title III also incorporates certain privacy and civil
liberties protections. It permits issuance of an interception warrant
only upon a judicial finding of probable cause to believe that the interception
will reveal evidence that “an individual is committing, has committed, or is
about to commit” certain particular criminal offenses.[9] Title
III also has minimization requirements—that is, it requires the adoption of
procedures to minimize the acquisition and retention of non-publicly available
information concerning non-consenting U.S. persons who are not the targets of
surveillance, unless such person’s identity is necessary to understand the law
enforcement information or assess its importance. In other words, if while
investigating a terrorist case, the wiretap intercepts a conversation with a
doctor, or a lover, or a pizza salesman that is not relevant to the
investigation, that conversation must be “minimized,” and information not
meeting that standard may not be disseminated.

Beyond this, the use of Title III warrants is subject to
periodic congressional review and oversight. Most significantly, electronic
evidence collected in violation of Title III may not be used as evidence in a
criminal case.

As Title III applies in the law enforcement context, the
Foreign Intelligence Surveillance Act (FISA) authorizes the collection of
communications for certain intelligence purposes. Passed in 1978, the Act
creates the mechanism by which such orders permitting the conduct of electronic
surveillance could be obtained from a specialized court—the Foreign
Intelligence Surveillance Court (FISC). This court was, initially, authorized
to issue orders for targeting electronic communications in the U.S. of both
U.S. and non-U.S. persons based on a showing of probable cause of clandestine
intelligence activities, sabotage, or terrorist activities, on behalf of a
foreign power. The law was subsequently expanded to authorize the court to
issue warrants for physical searches (1994), the use of pen registers/trap and
traces (1999), and the collection of business records (1999).

To obtain a FISC order authorizing surveillance, the
government must meet the same “probable cause” standard as in a criminal case:
it must make a showing of probable cause to believe that the target of the
electronic surveillance is a foreign power or an agent of a foreign power. And,
as with Title III, the law imposes minimization obligations on the agency
intercepting the communications.[10]

—While amending the laws authorizing wiretaps to accommodate
changes in technology has been, for the most part, a ministerial exercise of
amending legislation, the same cannot be said of maintaining the technical
capacity to tap into the ever-changing stream of communications.

Congress first attempted to address this problem through
the Communications Assistance for Law Enforcement Act, known as CALEA.[11] CALEA’s
purpose was to insure that law enforcement and the intelligence agencies would
not be left behind the technology curve, by requiring telecommunications
providers to build the ability to intercept communications into their evolving
communications systems.

CALEA dealt with a technically feasible requirement. Initially,
many digital telephone systems did not have interception capabilities built in.[12] CALEA
required providers to change how they built their telecommunications systems so
that they had that capacity—an effort that could be achieved, generally,
without interfering with subscriber services. (As an aside, CALEA also provided
for a federal monetary subsidy to the telecommunications providers to pay for
the changeover.)

As drafted in 1994, CALEA’s requirements were applicable
only to facilities-based telecommunications providers—that is, companies who
actually owned the lines and equipment used for the PSTN and Internet. “Information
services providers” (in other words, those who provide e-mail, instant
messaging, chat, and other communications platforms that are not dependent on traditional
telecommunications) were excluded, at least in part because those forms of
communication were still in their infancy and of relatively little importance.[13]

Finally, and perhaps most importantly, CALEA did not say
that telecommunications providers had to give government a way of decrypting
encrypted messages that were put on its network for transmission. A telecommunications
provider only had to decrypt messages if it provided the encryption services
itself. So if an individual independently used encryption at the origin of the
message, all that CALEA required is that the telecommunications provider should
have a means of intercepting the encrypted message available when authorized to
do so.

III. The
Wiretapping Problem Today

And hence the problem, which is two-fold: Cyber
criminals, cyber spies, and cyber warriors are increasingly migrating to
alternative communications systems—ones like Skype and virtual worlds that are
completed disconnected from the traditional PTSN networks covered by CALEA. And,
along the way, they are increasingly using encryption technology that prevents law
enforcement, counter-espionage, and counter-terrorism experts from having the
ability to listen in on communications.[14] On
the wiretapping front the problems are, again, both technical and legal.

Technologically, the distributed nature makes true
interception capabilities extremely difficult. In a peer-to-peer network there
is no centralized switching point. And in a packet switching system where the
message is broken in many parts, there is no place on the network where the
whole message is compiled, save at the two end points. While peer-to peer
systems can be used for illegal activity (e.g. illegal file sharing),[15] they
are also an integral part of legitimate file-sharing activities.[16]

Instead, the government must use sampling techniques to
intercept portions of a message and then, when a problematic message is
encountered, use sophisticated techniques to reassemble the entire message
(often by arranging for the whole message to be redirected to a government
endpoint). The FBI developed such a system in the late 1990s, called Carnivore.[17] It
was designed to “sniff” packets of information for targeted messages. When the
program became public, the uproar over this sort of interception technique
forced the FBI to end the program.

It is said that the National Security Agency (NSA) uses
a packet sniffing system, called Echelon, for intercepting foreign
communications traffic that is significantly more effective than Carnivore ever
was when deployed domestically.[18] Indeed,
according to the New York Times, the Echelon
system was at the core of the NSA’s post-9/11 domestic surveillance system. [19] While
little is publicly known about the capacity of the Echelon system, one observer
(an EU Parliamentary investigation) has estimated that the system could
intercept three million faxes, telephone calls, or e-mails per minute.[20]

In order for a system like Carnivore or Echelon to work,
however, the routing system must insure either that traffic is routed to the
sniffer along the way or that the sniffer is physically located between the two
endpoints of the communication. But, therein lies the problem—many of the
peer-to-peer systems are not configured to route traffic to law enforcement

IV. Changing
Law—Addressing New Challenges

To address these problems, the U.S. government has
spoken publicly of its intent to seek an amendment to CALEA. According to public reports, the government would seek to extend CALEA’s
wiretapping requirements for traditional telecommunications providers to digital
communications technologies. Doing so would, according to the government, close
a growing gap in existing surveillance capabilities that increasingly places
criminal or espionage activity behind a veil that the government cannot pierce.

The proposed changes would have three components: 1) expansion
of CALEA’s decryption requirement to all communications service providers who
give their users an ability to encrypt their messages;[21] 2) a requirement that foreign-based service providers doing business in the
United States have a domestic office to which the government may go where
interceptions can take place; and 3) apparently, a requirement that providers
of peer-to-peer communications systems (like Skype) alter their software to allow
interception of distributed communications. The government, speaking through Valerie
Caproni, the General Counsel for the FBI, has argued that these proposed
changes (which are expected to be the subject of legislative consideration in
the coming year) would not give additional wiretapping authority to law
enforcement officials, but simply extend existing authority “in order to
protect the public safety and national security.”[22]

The government’s proposal poses any number of
challenging legal and policy issues that will need to be addressed when (or if)
Congress gets around to considering the question (some of these are issues
unique to American consideration, others will be repeated globally).

The principal legal issues will, as before, involve
authorization rules and standards for operation. Presumably, if the government
is to be taken at its word, they will be seeking no greater interception
authority than exists today for wire communications—routinized access to
non-content “header information” joined with a probable cause standard for
access to “content.”

In some conceptions, the CALEA expansion might also
implicate the Fifth Amendment protection against self-incrimination. Imagine an
individual who encrypts messages he sends across the Internet. The courts have
yet to determine whether or not an effort to compel that individual to disclose
the decryption key constitutes a violation of his Fifth Amendment privilege. In
general, the answer to the question will turn on whether disclosing the
decryption key is thought of more like the production of a physical object
(such as the physical key to a lock box), which may be compelled, or like the
production of a person’s mental conceptions (such as the memorized combination
to a safe), which may not be.[23]

These Fifth Amendment considerations are likely to be of
limited applicability. Even in many peer-to-peer applications (like Skype), the
encryption keys are held by a centralized provider who uses the user-generated
keys to enable encrypted communications from a variety of different platforms
where the user might log in. In effect, to make the system more convenient, the
user allows a third-party coordinator (here, Skype) to have access to the key. In
doing so, Fifth Amendment protections are likely waived.

At bottom, however, the issues raised by the nascent
proposal are more policy questions than legal questions. Consider a short list
of these sorts of questions:

Is implementation of an expanded CALEA even technically
feasible in all cases? How will software developers who are providing
peer-to-peer services provide access to communications when there is no
centralized point in the network through which the data will have to pass? Presumably
this will require developers to reconfigure their software products in ways
that permit the interception and decryption.

Think, for example, of an open-platform encryption
program like TrueCrypt, where users retain sole possession of their own
generated encryption keys. Here, the users might retain Fifth Amendment rights
against self-incrimination that would protect them against the compelled
disclosure of their keys—but could CALEA be amended to require that software
commercial vendors who manufacture such programs include decryption back-doors?
The answer is unclear.

And if they
could, what then? Depending on how broad the modified CALEA requirements are,
the economic costs of modifying existing platforms could run into the hundreds
of millions, if not billions, of dollars. When CALEA was first implemented, the
federal government made funds available to offset the costs of the upgrades.[24] Would it do so again, and to what degree?

More significantly, what would be the security
implications of requiring interception capabilities in new technologies? Building
in these capabilities would necessarily introduce potential vulnerabilities
that could be exploited, not by those who would have authorized access, but
rather by hackers who found a way to crack the capabilities of the protection

And, finally, there are issues to be considered in
connection with international perceptions of American conduct. In recent months,
there has been a spate of efforts by various foreign governments to secure
access to Internet communications.[26] It
is difficult, if not impossible, for the United States to oppose such efforts
in international fora when its own policy favors expansions of interception
capabilities domestically. Indeed, our stated public policy favors Internet
freedom, in large part as a way of energizing democracy movements around the
policy that is difficult to square with a domestic move toward greater
governmental interception capabilities.


Changing technology has run ahead far faster than the
law has. Existing wiretapping laws will, at a minimum, need to be updated to reflect
the changing architecture of distributed communications. More fundamentally, we
will need to consider whether (or not) to mandate the development of technology
in a particular direction for the purposes of enabling governmental activities.
Doing so will surely have positive investigative benefits for the government,
but there will undoubtedly be collateral legal, economic, and political
ramifications of such a requirement.


[1] Vikas Bajaj, India May Be Near Resolution of BlackBerry
, N.Y.
, Aug. 17, 2010, available at

[2] Charlie Savage, U.S. Wants to Make It Easier to Wiretap the
, N.Y.
, Sept. 27, 2010, available

[3] Jeffrey Yeates, CALEA and the
RIPA: the U.S. and the U.K. Responses to Wiretapping in an Increasingly
Wireless World
, 12 Alb. L.J. Sci.
& Tech.
125, 135-36 (2001).

[4] In the film He’s Just Not That Into You (New Line Cinema 2009), one of the characters, Mary (played by Drew Barrymore),
bemoans the proliferation of communications methods: “I had this guy leave me a
voicemail at work, so I called him at home, and then he e-mailed me to my
BlackBerry, and so I texted to his cell, and now you just have to go around
checking all these different portals just to get rejected by seven different

[5] IETF Policy on
Wiretapping, May 2000,

[6] 389 U.S. 347 (1967).

[7] Title III is now codified in the United States Code at 18 U.S.C. §§ 2510-22.

[8] Electronic Communications Privacy Act of 1986, Pub. L.
No. 99-508, 100 Stat. 1848 (1986) (codified at 18 U.S.C. § 2510).

[9] The list of offenses can be found at 18 U.S.C. § 2516.

[10] The law makes clear that
U.S. persons cannot be targeted solely on the basis of their lawful business or
political relationships with foreign governments or organizations, or on the
basis of other activities protected by the First Amendment.

[11] Communications Assistance for Law Enforcement Act, Pub. L. No.
102-414, 108 Stat. 4279 (1994) (now codified at 47 U.S.C. § 1001-1021).

[12] Dan Eggen & Jonathan Krim, Easier
Internet Wiretaps Sought; Justice Dept., FBI Want Consumers to Pay the Cost
Wash. Post, Mar. 13, 2004, at A01;
Marcia Coyle, Wiretaps Coming to
Internet; Critics Considering Legal Challenges
, Nat’l L.J., Aug. 15, 2005, at P1.

[13] Initially, Voice over IP (VoIP)
services (that is, telephone-type connections using the web instead of phone
lines for the connection) were excluded from CALEA. In 2006 interconnected VoIP
services (i.e. any service where a portion of the call was connected to a PTSN,
like the service provided by Vonage) were included under CALEA.
See In re Commc’ns Assistance for Law Enforcement Act & Broadband Access
& Servs., 20 F.C.C.R. 14989, ¶¶ 9-37 (2005).

[14] Charlie Savage, U.S. Tries to Make It Easier to Wiretap the Internet, N.Y. Times, Sept. 27, 2010, available at

[15] Napster, for example was the first peer-to-peer network
used for large-scale music sharing. Since then, there have been dozens of
similar file sharing programs, many used for seemingly illicit purposes.

[16] For example, Ubuntu Linux and World of Warcraft patches
are distributed using the BitTorrent protocol.

[17] John C. K. Daly, Echelon—the Ultimate
Spy Network?
, United P. Int’l,
Mar. 1, 2004,

[18] Duncan Campbell, Inside
Echelon: The History, Structure and Function of the Global Surveillance System
Known as Echelon
, Echelon On Line,
July 25, 2000,

[19] James Risen & Eric Lichtblau, Bush
Lets US Spy on Callers Without Courts
, N.Y.
, Dec. 16, 2005, at A1.

[20] Daly, supra note 17.

[21] Google, for example, now encrypts all e-mail in its system, while in transit,
unless a user opts out of the encryption policy and chooses to send his e-mail
unencrypted. Presumably, under the government’s proposal Google would need to
re-engineer its system to allow decryption upon receipt of an authorized
government request.

[22] Savage, supra note 14.

[23] The contrasting formulations were posited as useful analogies in Doe v. United States, 487 U.S. 201
(1988). In Doe, the signing of a
blank bank consent form was considered more like the production of a physical
object. By contrast in Hubbell v. United
, 530 U.S. 27 (2000), the documents produced by the defendant in
response to a subpoena were organized and selected through his own mental
analysis and thus protected from disclosure. Few court cases have addressed the encryption
question directly: Two, United States v. Rogozin, 2010 WL 4628520
(W.D.N.Y. Nov. 16. 2010) and United States v. Kirschner, 2010 WL 1257355
(E.D. Mich. March 30, 2010) thought that the password could not be compelled,
while another, In re Boucher, 2009 WL 424718, *1 (D. Vt. 2009), available
was decided on the technicality that Boucher had already given the government
access to his computer once, so he could not object to doing so a second time
and disclosing his encryption key.

[24] See FBI
& Dept. of Justice, Communications Assistance for Law Enforcement Act
(CALEA) Implementation Plan
, Part V, Mar. 3, 1997, available at

[25] When the Clipper chip (a chip to allow decryption of encrypted phone traffic)
was first introduced, flaws in it were quickly found. See Matt Blaze, Protocol
Failure in the Escrowed Encryption Standard
(Aug. 20, 1994), available at
More recently, Greek official communications were intercepted illegally through
a security flaw created by the inclusion of built-in interception feature. See Vodafone
Greece Rogue Phone Taps: Details at Last
, H
, available at

[26] In addition to the Indian example mentioned at the outset, see UAE Crackdown on BlackBerry Services to Extend
to Foreign Visitors
, Wash. Post,
Aug. 3, 2010, available at

[27] Hillary Clinton, Remarks on
Internet Freedom, Jan. 21, 2010, available