Anonymity Loves Company:
Usability and the Network Eﬀect
Roger Dingledine and Nick Mathewson
The Free Haven Project
Abstract. A growing ﬁeld of literature is studying how usability im-
pacts security . One class of security software is anonymizing networks—
overlay networks on the Internet that provide privacy by letting users
transact (for example, fetch a web page or send an email) without re-
vealing their communication partners.
In this position paper we focus on the network eﬀects of usability on
privacy and security: usability is a factor as before, but the size of the
user base also becomes a factor. We show that in anonymizing networks,
even if you were smart enough and had enough time to use every system
perfectly, you would nevertheless be right to choose your system based
in part on its usability for other users.
1 Usability for others impacts your security
While security software is the product of developers, the security it provides is
a collab oration between developers and users. It’s not enough to make software
that can be used securely—software that is hard to use often suﬀers in its security
as a result.
For example, suppose there are two popular mail e ncryption programs: Heavy-
Crypto, which is more secure (when used correctly), and LightCrypto, which is
easier to use. Suppose you can use either one, or both. Which should you choose?
You might dec ide to use HeavyCrypto, since it protects your secrets better.
But if you do, it’s likelier that when your friends send you conﬁdential email,
they’ll make a mistake and encrypt it badly or not at all. With LightCrypto,
you can at least be more certain that all your friends’ correspondence with you
will get some protection.
What if you used both programs? If your tech-savvy friends use HeavyCrypto,
and your less sophisticated friends use LightCrypto, then everybody will get as
much protection as they can. But can all your friends really judge how able they
are? If not, then by supporting a less usable option, you’ve made it likelier that
your non-savvy friends will shoot themselves in the foot.
The crucial insight here is that for email encryption, security is a collabora-
tion between multiple p eople: both the sender and the receiver of a secret email
must work together to protect its conﬁdentiality. Thus, in order to protect your
own security, you need to make sure that the system you use is not only usable
by yourself, but by the other participants as well.
This observation doesn’t mean that it’s always better to choose usability over
security, of course: if a system doesn’t address your threat model, no amount
of usability can make it secure. But conversely, if the people who need to use a
system can’t or won’t use it correctly, its ideal security properties are irrelevant.
Hard-to-use programs and proto c ols c an hurt security in many ways:
• Programs with insecure modes of operation are bound to b e used unknow-
ingly in those modes.
• Optional security, once disabled, is often never re-enabled. For example,
many users who ordinarily disable browser cookies for privacy reasons wind
up re-enabling them so they can access sites that require cookies, and later
leaving cookies enabled for all sites.
• Badly labeled oﬀ switches for security are even worse: not only are they more
prone to accidental selection, but they’re more vulnerable to social attackers
who trick users into disabling their security. As an example, consider the
page-long warning your browser provides when you go to a website with an
expired or otherwise suspicious SSL certiﬁcate.
• Inconvenient security is often abandoned in the name of day-to-day eﬃ-
ciency: pe ople often write down diﬃcult passwords to keep from forgetting
them, and share passwords in order to work together.
• Systems that provide a false sense of security prevent users from taking real
measures to protect themselves: breakable encryption on ZIP archives, for
example, can fool users into thinking that they don’t need to encrypt email
containing ZIP archives.
• Systems that provide bad mental models for their security can trick users
into believing they are more safe than they really are: for example, many
users interpret the “lock” icon in their web browsers to mean “You can safely
enter personal information,” when its meaning is closer to “Nobody can read
your information on its way to the named website.”
2 Usability is even more important for privacy
We described above that usability aﬀects security in systems that aim to pro-
tect data conﬁdentiality. But when the goal is privacy, it can become e ven more
important. Anonymizing networks such as Tor , JAP , Mixminion , and
Mixmaster  aim to hide not only what is being said, but also who is com-
municating with whom, which users are using which websites, and so on. These
systems have a broad range of users, including ordinary citizens who want to
avoid being proﬁled for targeted advertisements, corporations who don’t want
to reveal information to their competitors, and law enforcement and government
intelligence agencies who need to do operations on the Internet without being
Or more accurately, “Nobody can read your information on its way to s omeone who
was able to convince one of the dozens to hundreds of CAs conﬁgured in your browser
that they are the named website, or who was able to compromise the named website
later on. Unless your computer has been compromised already.”
Anonymity networks work by hiding users among users. An eavesdropper
might be able to tell that Alice, Bob, and Carol are all using the network, but
should not be able to tell which of them is talking to Dave. This property is
summarized in the notion of an anonymity set—the total set of people who,
so far as the attacker can tell, might be the one engaging in some activity of
interest. The larger the set, the more anonymous the participants.
users join the network, existing users become more secure, even if the new users
never talk to the existing ones! [1, 2] Thus, “anonymity loves company.”
In a data conﬁdentiality system like PGP, Alice and Bob can decide by
themselves that they want to get security. As long as they both use the software
prop e rly, no third party can intercept the traﬃc and break their encryption.
However, Alice and Bob can’t get anonymity by themselves: they need to par-
ticipate in an infrastructure that coordinates users to provide cover for each
No organization can build this infrastructure for its own sole use. If a single
corporation or government agency were to build a private network to protect its
operations, any connections entering or leaving that network would be obviously
linkable to the controlling organization. The members and operations of that
agency would be easier, not harder, to distinguish.
Thus, to provide anonymity to any of its users, the network must accept
traﬃc from external users, so the various user groups can blend together.
In practice, existing commercial anonymity s olutions (like Anonymizer.com)
are based on a se t of single-hop proxies. In these systems, each user connects
to a single proxy, which then relays the use r’s traﬃc. Single proxies provide
comparatively weak security, since a compromised proxy can trivially observe
all of its users’ actions, and an eavesdropper only needs to watch a single proxy
to perform timing correlation attacks against all its users’ traﬃc. Worse, all users
need to trust the proxy company to have good security itself as well as to not
reveal user activities.
The solution is distributed trust: an infrastructure made up of many inde-
pendently controlled proxies that work together to make sure no transaction’s
privacy relies on any single proxy. With distributed-trust anonymity networks,
users build tunnels or circuits through a series of servers. They encrypt their
traﬃc in multiple layers of encryption, and each se rver removes a single layer of
encryption. No single server knows the entire path from the user to the user’s
chosen destination. Therefore an attacker can’t break the user’s anonymity by
compromising or eavesdropping on any one server.
Assuming that all participants are equally plausible, of course. If the attacker sus-
pects Alice, Bob, and Carol equally, Alice is more anonymous than if the attacker
is 98% suspicious of Alice and 1% suspicious of Bob and Carol, even though the
anonymity sets are the same size. Because of this imprecision, research is moving
beyond simple anonymity sets to more sophisticated measures based on the attacker’s
conﬁdence [7, 14].
This catch-phrase was ﬁrst made popular in our context by the authors of the
Crowds  anonymity network.
Despite their increased security, distributed-trust anonymity networks have
their disadvantages. Because traﬃc needs to be relayed through multiple servers,
performance is often (but not always) worse. Also, the software to implement a
distributed-trust anonymity network is signiﬁcantly more diﬃcult to design and
Beyond these issues of the architecture and ownership of the network, how-
ever, there is another catch. For users to keep the same anonymity set, they need
to act like each other. If Alice’s client acts completely unlike Bob’s client, or if
Alice’s messages leave the system ac ting completely unlike Bob’s, the attacker
can use this information. In the worst case, Alice’s messages stand out entering
and leaving the network, and the attacker can treat Alice and those like her as
if they were on a s eparate network of their own. But even if Alice’s messages
are only recognizable as they leave the network, an attacker can use this infor-
mation to break exiting messages into “messages from User1,” “messages from
User2,” and so on, and can now get away with linking messages to their senders
as groups, rather than trying to guess from individual messages [6, 11]. Some of
this partitioning is inevitable: if Alice speaks Arabic and Bob speaks Bulgarian,
we can’t force them both to learn English in order to mask each other.
What does this imply for usability? More so than with encryption systems,
users of anonymizing networks may nee d to choose their systems based on how
usable others will ﬁnd them, in order to get the protection of a larger anonymity
3 Case study: usability means users, users mean security
We’ll consider an example. Practical anonymizing networks fall into two broad
classes. High-latency networks like Mixminion or Mixmaster can resist strong
attackers who can watch the whole network and control a large part of the
network infrastructure. To prevent this “global attacker” from linking senders to
recipients by correlating when messages enter and leave the system, high-latency
networks introduce large delays into message delivery times , and are thus only
suitable for applications like email and bulk data delivery—most users aren’t
willing to wait half an hour for their web pages to load. Low-latency networks
like Tor, on the other hand, are fast enough for web browsing, secure shell, and
other interactive applications, but have a weaker threat model: an attacker who
watches or controls both ends of a communication can trivially correlate message
timing and link the communicating parties [5, 10].
Clearly, users who need to resist strong attackers must choose high-latency
networks or nothing at all, and users who need to anonymize interactive appli-
cations must choose low-latency networks or nothing at all. But what should
ﬂexible users choose? Against an unknown threat model, with a non-interactive
application (such as email), is it more secure to choose security or usability?
Security, we might decide. If the attacker turns out to be strong, then we’ll
prefer the high-latency network, and if the attacker is weak, then the extra
protection doesn’t hurt.
But since many users might ﬁnd the high-latency network inconvenient, sup-
pose that it gets few actual users—so few, in fact, that its maximum anonymity
set is too small for our needs. In this case, we need to pick the low-latency sys-
tem, since the high-latency system, though it always protects us, never protects
us enough; whereas the low-latency system can give us enough protection against
at least some attackers.
This decision is especially messy because even the developers who implement
these anonymizing networks can’t recommend which approach is safer, since they
can’t predict how many users each network will get and they can’t predict the
capabilities of the attackers we might see in the wild. Worse, the anonymity
research ﬁeld is still young, and doesn’t have many convincing techniques for
measuring and comparing the protection we get from various situations. So even
if the developers or users could somehow divine what level of anonymity they
require and what their expected attacker can do, the researchers still don’t know
what parameter values to recommend.
4 Case study: against options
Too often, designers faced with a security decision bow out, and instead leave
the choice as an option: protocol designers leave implem entors to decide, and
implementors leave the choice for their users. This approach can be bad for
security systems, and is nearly always bad for privacy systems.
• Extra options often delegate security decisions to those least able to under-
stand what they imply. If the protocol designer can’t decide whether the
AES encryption algorithm is better than the Twoﬁsh encryption algorithm,
how is the end user supposed to pick?
• Options make code harder to audit by increasing the volume of code, by
increasing the number of possible conﬁgurations exponentially, and by guar-
anteeing that non-default conﬁgurations will receive little testing in the ﬁeld.
If AES is always the default, even with several independent implementations
of your protocol, how long will it take to notice if the Twoﬁsh implementation
Most users stay with default conﬁgurations as long as they work, and only
reconﬁgure their software as necess ary to make it usable. For e xample, suppose
the developers of a web browser can’t decide whether to support a given exten-
sion with unknown security implications, so they le ave it as a user-adjustable
option, thinking that users can enable or disable the extension based on their
security needs. In reality, however, if the extension is enabled by default, nearly
all users will leave it on whether it’s secure or not; and if the extension is dis-
abled by default, users will tend to enable it based on their perceived demand
for the extension rather than their security nee ds. Thus, only the most savvy
and security-conscious users—the ones who know more about web security than
the developers themselves—will actually wind up understanding the security
implications of their decision.
The real issue here is that designers often end up with a situation where they
need to choose betwe en ‘insecure’ and ‘inconvenient’ as the default conﬁguration—
meaning they’ve already made a mistake in designing their application.
Of c ourse, when end users do know more about their individual security
requirements than application designers, then adding options is beneﬁcial, espe-
cially when users describe their own s ituation (home or enterprise; shared versus
single-user host) rather than trying to specify what the program should do about
In privacy applications, sup erﬂuous options are even worse. When there are
many diﬀerent p oss ible conﬁgurations, eavesdroppers and insiders can often tell
users apart by which settings they choose. For example, the Type I or “Cypher-
punk” anonymous email network uses the OpenPGP encrypted message format,
which supports many symmetric and asymmetric ciphers. Because diﬀerent users
prefer diﬀerent ciphers, and be cause diﬀerent versions of encryption programs
implementing OpenPGP (such as PGP and GnuPG) use diﬀerent cipher suites,
users with uncommon preferences and versions stand out from the rest, and get
little privacy at all. Similarly, Type I allows users to pad their messages to a
ﬁxed size so that an eavesdropper can’t correlate the sizes of messages passing
through the network—but it forces the user to decide what size of padding to
use! Unless a user can guess which padding size will happen to be most popular,
the option provides attackers with another way to tell users apart.
Even when users’ needs genuinely vary, adding options does not necessarily
serve their privacy. In practice, the default option usually prevails for casual
users, and therefore needs to prevail for security-conscious users even when it
would not otherwise be their best choice. For example, when an anonymizing
network allows user-selected message latency (like the Type I network does),
most users tend to use whichever setting is the default, so long as it works.
Of the fraction of users who change the default at all, most will not, in fact,
understand the security implications; and those few who do will need to decide
whether the increased traﬃc-analysis resistance that comes with more variable
latency is worth the decreased anonymity that comes from splitting away from
the bulk of the user base.
5 Case study: Mixminion and MIME
We’ve argued that providing too many observable options can hurt privacy, but
we’ve also argued that focusing too hard on privacy over usability can hurt
privacy itself. What happens when these principles conﬂict?
We encountered such a situation when designing how the Mixminion anony-
mous email network  should handle MIME-encoded data. MIME (Multipur-
pose Internet Mail Extensions) is the way a mail client tells the receiving mail
client about attachments, which character set was used, and so on. As a stan-
dard, MIME is so permissive and ﬂexible that diﬀerent email programs are al-
most always distinguishable by which s ubsets of the format, and which types of
encodings, they choose to generate. Trying to “normalize” MIME by convert-
ing all mail to a standard only works up to a point: it’s trivial to convert all
encodings to quoted-printable, for example, or to impose a standard order for
multipart/alternative parts; but demanding a uniform list of formats for multi-
part/alternative messages, normalizing HTML, stripping identifying information
from Microsoft Oﬃce documents, or imposing a single character encoding on each
language would likely be an impossible task.
Other possible solutions to this problem could include limiting users to a
single email client, or simply banning email formats other than plain 7-bit ASCII.
But these procrustean approaches would limit usability, and turn users away
from the Mixminion network. Since fewer users mean less anonymity, we must
ask whether users would be better oﬀ in a larger network where their messages
are likelier to be distinguishable based on email client, or in a smaller network
where everyone’s email formats look the same.
Some distinguishability is inevitable anyway, since users diﬀer in their inter-
ests, languages, and writing styles: if Alice writes about astronomy in Amharic,
her messages are unlikely to be mistaken for Bob’s, who writes about botany in
Basque. Also, any attempt to restrict formats is likely to backﬁre. If we limited
Mixminion to 7-bit ASCII, users wouldn’t stop sending each other images, PDF
ﬁles, and messages in Chinese: they would instead follow the same evolutionary
path that led to MIME in the ﬁrst place, and encode their messages in a variety
of distinguishable formats, with each client software implementation having its
own ad hoc favorites. So imposing uniformity in this place would not only drive
away users, but would probably fail in the long run, and lead to fragmentation
at least as dangerous as we were trying to avoid.
We also had to consider threat models. To take advantage of format dis-
tinguishability, an attacker needs to observe messages leaving the network, and
either exploit prior knowledge of suspected senders (“Alice is the only user who
owns a 1995 copy of Eudora”), or feed message format information into traﬃc
analysis approaches (“Since half of the messages to Alice are written in English,
I’ll assume they mostly come from diﬀerent senders than the ones in Amharic.”).
Neither attack is certain or easy for all attackers; even if we can’t defeat them
in the worst possible case (where the attacker knows, for example, that only
one copy of LeetMailPro was ever sold), we can provide vulnerable users with
protection against weaker attackers.
In the end, we compromised: we perform as much normalization as we can,
and warn the user about document types such as MS Word that are likely to re-
veal identifying information, but we do not forbid any particular format or client
software. This way, users are informed about how to blend with the largest pos-
sible anonymity set, but users who prefer to use distinguishable formats rather
than nothing at all still receive and contribute protection against certain attack-
6 Case study: Tor Installation
Usability and marketing have also proved important in the development of Tor,
a low-latency anonymizing network for TCP traﬃc. The technical challenges Tor
has solved, and the ones it still needs to address, are described in its design pap er
, but at this point many of the most crucial challenges are in adoption and
While Tor was in it earliest s tages , its user base was a small number of fairly
sophisticated privacy enthusiasts with experience running Unix services, who
wanted to experiment with the network (or so they say; by design, we don’t track
our users). As the project gained more attention from venues including security
conferences, articles on Slashdot.org and Wired News, and more mainstream
media like the New York Times, Forbes, and the Wall Street Journal, we added
more users with less technical expertise. These users can now provide a broader
base of anonymity for high-needs users, but only when they receive good support
For example, it has proven diﬃcult to educate less sophisticated users about
DNS issues. Anonymizing TCP streams (as Tor does) does no good if appli-
cations reveal where they are about to connect by ﬁrst p erforming a non-
anonymized hostname lookup. To stay anonymous, users need either to conﬁgure
their applications to pass hostnames to Tor directly by using SOCKS4a or the
hostname-based variant of SOCKS5; to manually resolve hostnames with Tor
and pass the resulting IPs to their applications; or to direct their applications to
application-sp e ciﬁc proxies which handle each protocol’s needs independently.
None of these is easy for an unsophisticated user, and when they misconﬁgure
their systems, they not only compromise their own privacy, but also provide no
cover for the users who are conﬁgured correctly: if Bob leaks a DNS request
whenever he is about to connect to a website, an observer can tell that anybody
connecting to Alice’s website anonymously must not be Bob. Thus, experienced
users have an interest in making sure inexperienced users can use the system
correctly. Tor being hard to conﬁgure is a weakness for everybo dy.
We’ve tried a few solutions that didn’t work as well as we hoped. Improving
documentation only helped the users who read it. We changed Tor to warn users
who provided an IP address rather than a hostname, but this warning usually
resulted in several e mail exchanges to explain DNS to the casual user, who had
typically no idea how to solve his problem.
At the time of this writing, the most important solutions for these users have
been to improve Tor’s documentation for how to conﬁgure various applications
to use Tor; to change the warning messages to refer users to a description of the
solution (“You are insecure. See this webpage.”) instead of a description of the
problem (“Your application is sending IPs instead of hostnames, which may leak
information. Consider using SOCKS4a instead.”); and to bundle Tor with the
support tools that it needs, rather than relying on users to ﬁnd and conﬁgure
them on their own.
7 Case study: JAP and its anonym-o-meter
The Java Anon Proxy (JAP) is a low-latency anonymizing network for web
browsing developed and deployed by the Technical University of Dresden in
Germany . Unlike Tor, which uses a free-route topology where each user can
choose where to enter the network and where to exit, JAP has ﬁxed-route cas-
cades that aggregate user traﬃc into a single entry point and a single exit point.
The JAP client includes a GUI:
Notice the ‘anonymity meter’ giving the user an impression of the level of
protection for his current traﬃc.
How do we decide the value that the anonym-o-meter should report? In JAP’s
case, it’s based on the number of other users traveling through the cascade at
the same time. But alas, since JAP aims for quick transmission of bytes from
one end of the cascade to the other, it falls prey to the same end-to-end timing
correlation attacks as we described above. That is, an attacker who can watch
both ends of the cascade won’t ac tually be distracted by the other users [5,
10]. The JAP team has plans to implement full-scale padding from every user
(sending and receiving packets all the time even when they have nothing to
send), but—for usability reasons—they haven’t gone forward with these plans.
As the system is now, anonymity sets don’t provide a real measure of security
for JAP, since any attacker who can watch both ends of the cascade wins, and
the numbe r of users on the network is no real obstacle to this attack. However,
we think the anonym-o-meter is a great way to present security information to
the user, and we hope to see a variant of it deployed one day for a high-latency
system like Mixminion, where the amount of current traﬃc in the system is more
directly related to the protection it oﬀers.
8 Bootstrapping, conﬁdence, and reputability
Another area where human factors are critical in privacy is in bootstrapping
new systems. Since new systems start out with few users, they initially provide
only small anonymity sets. This starting state creates a dilemma: a new system
with improved privacy properties will only attract users once they believe it is
popular and therefore has high anonymity sets; but a system cannot be popular
without attracting users. New systems need users for privacy, but need privacy
Low-needs users can break the deadlock . The earliest stages of an anonymiz-
ing network’s lifetime tend to involve users who need only to resist weak attack-
ers who can’t know which users are using the network and thus can’t learn the
contents of the small anonymity set. This solution reverses the early adopter
trends of many security systems : rather than attracting ﬁrst the most security-
conscious users, privacy applications must begin by attracting low-needs users
But this analysis relies on users’ accurate perceptions of present and future
anonymity set size. As in market economics, expectations themselves can bring
about trends: a privacy system which people believe to be secure and popular
will gain users, thus becoming (all things equal) more secure and popular. Thus,
security depends not only on usability, but also on perceived usability by others,
and hence on the quality of the provider’s marketing and public relations. Per-
versely, over-hyped systems (if they are not too broken) may be a better choice
than modestly promoted ones, if the hype attracts more users.
Yet another factor in the safety of a given network is its reputability: the
perception of its social value based on its current users. If I’m the only user of a
system, it might be socially accepted, but I’m not getting any anonymity. Add a
thousand Communists, and I’m anonymous, but everyone thinks I’m a Commie.
Add a thousand random citizens (cancer survivors, privacy enthusiasts, and so
on) and now I’m hard to proﬁle.
The more cancer survivors on Tor, the be tter for the human rights activists.
The more script kiddies, the worse for the normal users. Thus, reputability is
an anonymity issue for two reasons. First, it impacts the sustainability of the
network: a network that’s always about to be shut down has diﬃculty attracting
and keeping users, so its anonymity set suﬀers. Second, a disreputable network
attracts the attention of p owerful attackers who may not m ind revealing the
identities of all the users to uncover the few bad ones.
While people therefore have an incentive for the network to be used for “more
reputable” activities than their own, there are still tradeoﬀs involved when it
comes to anonymity. To follow the ab ove example, a network used entirely by
cancer survivors might welcome some Communists onto the network, though of
course they’d prefer a wider variety of users.
The impact of public perception on security is esp e cially important during
the bootstrapping phase of the network, where the ﬁrst few widely publicized
uses of the network can dictate the types of users it attracts next.
9 Technical challenges to guessing the number of users in
In addition to the social problems we describe above that make it diﬃcult for a
typical user to guess which anonymizing network will be most popular, there are
some technical challenges as well. These stem from the fact that anonymizing
networks are good at hiding what’s going on—even from their users. For example,
one of the toughest attacks to solve is that an attacker might sign up many users
to artiﬁcially inﬂate the apparent size of the network. Not only does this Sybil
attack increase the o dds that the attacker will be able to successfully compromise
a given user transaction , but it might also trick users into thinking a given
network is safer than it actually is.
And ﬁnally, as we saw when discussing JAP above, the feasibility of end-to-
end attacks makes it hard to guess how much a given other user is contributing
to your anonymity. Even if he’s not actively trying to trick you, he can still
fail to provide cover for you, either because his behavior is suﬃciently diﬀerent
from yours (he’s active during the day, and you’re active at night), because
his transactions are diﬀerent (he talks about physics, you talk about AIDS), or
because network design parameters (such as low delay for messages) mean the
attacker is able to track transactions more easily.
10 Bringing it all together
Users’ safety relies on them behaving like other users. But how can they predict
other users’ behavior? If they need to behave in a way that’s diﬀerent from the
rest of the users, how do they compute the tradeoﬀ and risks?
There are several lessons we might take away from researching anonymity
and usability. On the one hand, we might remark that anonymity is already
tricky from a technical standpoint, and if we’re required to get usability right as
well before anybody can be safe, it will be hard indeed to come up with a good
design: if lack of anonymity means lack of users, then we’re stuck in a depressing
loop. On the other hand, the loop has an optimistic side too. Good anonymity
can mean more users: if we can make good headway on usability, then as long
as the technical designs are adequate, we’ll end up with enough users to make
everything work out.
In any case, declining to design a good solution means leaving most users to
a less secure network or no anonymizing network at all. Cancer survivors and
abuse victims would continue communications and research over the Internet,
risking social or employment problems; and human rights workers in oppressive
countries would continue publishing their stories.
The temptation to focus on designing a perfectly usable system before build-
ing it can b e self-defeating, since obstacles to usability are often unforeseen. We
believe that the security community needs to focus on continuing experimental
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