Identifying and avoiding weak cryptography products.
Snake Oil Warning Signs:
Encryption Software to Avoid
Copyright ╘ 1996-1998
Matt Curtin <email@example.com>
April 10, 1998
* Basic Concepts
o Symmetric vs. Asymmetric Cryptography
o Secrecy vs. Integrity: What are you trying to protect?
o Key Sizes
o Keys vs. Passphrases
o Implementation Environment
* Snake Oil Warning Signs
o ``Trust Us, We Know What We're Doing''
o Secret Algorithms
o Revolutionary Breakthroughs
o Experienced Security Experts, Rave Reviews, and Other Useless
o Algorithm or product X is insecure
o Recoverable Keys
o Exportable from the USA
o ``Military Grade''
* Other Considerations
Distribution of this document is unlimited. We're specifically trying to
reach people who are not experts in cryptography or security but find
themselves making decisions about what sorts of crypto (if any) to use, both
for their organizations and for themselves.
The Snake Oil FAQ is posted monthly to sci.crypt, alt.security,
comp.security, comp.answers, and comp.infosystems. It is available in
PostScript and PDF form (ideal for printing) via the web at
and HTML at
All contributors' employers will no doubt disown any statements herein.
We're not speaking for anyone but ourselves.
This is a compilation of common habits of snake oil vendors. It cannot be
the sole method of rating a security product, since there can be exceptions
to most of these rules. From time to time, a reputable vendor will produce
something that is actually quite good, but will promote it with braindead
marketing techniques. But if you're looking at something that exhibits
several warning signs, you're probably dealing with snake oil.
Every effort has been made to produce an accurate and useful document, but
the information herein is completely without warranty. This is a
work-in-progress; feedback is greatly appreciated. If you find any errors or
otherwise wish to contribute, please contact the document keeper, Matt
With the rise in the number of crypto products came a rise in the number of
ineffective or outright bogus products. After some discussion about this on
the cypherpunks list, Robert Rothenburg <firstname.lastname@example.org> wrote the
first iteration of the Snake Oil FAQ. Matt Curtin took the early text and
munged it into its current state with the help of the listed contributors
(and probably some others whose names have inadvertently missed. Sorry in
advance, if this is the case.)
The following folks have contributed to this FAQ.
Jeremey Barrett <email@example.com>
Steven M. Bellovin <firstname.lastname@example.org>
Matt Blaze <email@example.com>
Bo Dvmstedt <firstname.lastname@example.org>
Gary Ellison <email@example.com>
Larry Kilgallen <KILGALLEN@Eisner.DECUS.Org>
Dutra Lacerda <firstname.lastname@example.org>
Felix Lee <email@example.com>
Colin Plumb <firstname.lastname@example.org>
Jim Ray <email@example.com>
Terry Ritter <firstname.lastname@example.org>
Robert Rothenburg <email@example.com>
Adam Shostack <firstname.lastname@example.org>
Rick Smith <email@example.com>
Randall Williams <firstname.lastname@example.org>
Good cryptography is an excellent and necessary tool for almost anyone. Many
good cryptographic products are available commercially, as shareware, or
free. However, there are also extremely bad cryptographic products which not
only fail to provide security, but also contribute to the many
misconceptions and misunderstandings surrounding cryptography and security.
Why ``snake oil''? The term is used in many fields to denote something sold
without consideration of its quality or its ability to fulfill its vendor's
claims. This term originally applied to elixirs sold in traveling medicine
shows. The salesmen would claim their elixir would cure just about any
ailment that a potential customer could have. Listening to the claims made
by some crypto vendors, ``snake oil'' is a surprisingly apt name.
Superficially, it is difficult to distinguish snake oil from the Real Thing:
all encryption utilities produce garbled output. The purpose of this
document is to present some simple ``red flags'' that can help you detect
For a variety of reasons, this document does not mention specific products
or algorithms as being ``good'' or ``snake oil.''
In an effort to make this FAQ more complete, some basic information is
covered here. The Cryptography FAQ  is a more general tutorial of
cryptography and should also be consulted.
When evaluating any product, be sure to understand your needs. For data
security products, what are you trying to protect? Do you want a data
archiver, an e-mail plug-in, or something that encrypts on-line
communications? Do you need to encrypt an entire disk or just a few files?
And how secure is secure enough? Does the data need to be unreadable by
``spies'' for five minutes, one year, or 100 years? Is the spy someone's kid
sister, a corporation, or a government?
Symmetric vs. Asymmetric Cryptography
There are two basic types of cryptosystems: symmetric (also known as
``conventional'' or ``secret key'') and asymmetric (``public key.'')
Symmetric ciphers require both the sender and the recipient to have the same
key. This key is used by the sender to encrypt the data, and again by the
recipient to decrypt the data. The problem here is getting the sender and
recipient to share the key.
Asymmetric ciphers are much more flexible from a key management perspective.
Each user has a pair of keys: a public key and a private key. Messages
encrypted with one key can only be decrypted by the other key. The public
key can be published widely while the private key is kept secret.
So if Alice wishes to send Bob some secrets, she simply finds and verifies
Bob's public key, encrypts her message with it, and mails it off to Bob.
When Bob gets the message, he uses his private key to decrypt it.
Verification of public keys is an important step. Failure to verify that the
public key really does belong to Bob leaves open the possibility that Alice
is using a key whose associated private key is in the hands of an enemy.
Asymmetric ciphers are much slower than their symmetric counterparts. Also,
key sizes generally must be much larger. See the Cryptography FAQ  for a
more detailed discussion of these topics.
Secrecy vs. Integrity: What are you trying to protect?
For many users of computer-based crypto, preserving the contents of a
message is as important as protecting its secrecy. Damage caused by
tampering can often be worse than damage caused by disclosure. For example,
it may be disquieting to discover that a hacker has read the contents of
your funds-transfer authorization, but it's a disaster for him to change the
transfer destination to his own account.
Encryption by itself does not protect a message from tampering. In fact,
there are several techniques for changing the contents of an encrypted
message without ever figuring out the encryption key. If the integrity of
your messages is important, don't rely on just secrecy to protect them.
Check how the vendor protects messages from undetected modification.
Even if a cipher is secure against analytical attacks, it will be vulnerable
to brute-force attacks if the key is too small. In a brute-force attack, the
attacker simply tries every possible key until the right one is found. How
long this takes depends on the size of the key and the amount of processing
power available. So when trying to secure data, you need to consider how
long it must remain secure and how much computing power an attacker can use.
 and  offer some guidelines for choosing an appropriate key length.
For instance, Table 1 shows the cost of breaking symmetric keys by brute
force, as noted by . This same report strongly recommends using symmetric
keys of 90 bits or more.
With the tremendous increases in computing power over the last several
decades, cryptosystems which were once considered secure are now vulnerable
to brute-force attacks. RSA Laboratories sponsored a series of contests,
collectively known as the 1997 Secret Key Challenge . So far, we have
seen RC5 up to 56 bits fall victim to brute force attacks, as well as the
financial industry's workhorse, DES. At 56 bits, the keys used for DES are
just too small to stand up to a dedicated attacker. It's noteworthy that
both of the groups to break a DES-encrypted message did so with essentially
Table 1: Time and Cost of Key Recovery
Type of Time and Cost per Length Needed for
Attacker Budget Tool 40-bit Key Protection in Late
Pedestrian Tiny Computer Time 1 Week 45
$400 FPGA 5 Hours ($0.08) 50
Small business $10,000 FPGA 12 Minutes 55
FPGA 24 seconds
Department $300K ------------------------------
.005 seconds 60
FPGA .7 seconds
Big Company $10M .0005 seconds
Intelligence .0002 seconds
Agency $300M ASIC ($0.001) 75
As mentioned earlier, asymmetric ciphers typically require significantly
longer keys to provide the same level of security as symmetric ciphers.
Comparing key lengths between algorithms is awkward because different
algorithms have different characteristics. Knowing the key size is useless
if you don't know what type of algorithm is being used.
But to give you some idea of what's reasonable, Table 2, from , compares
symmetric keys against one type of asymmetric key: those based on the
``factoring problem'' or the ``discrete log problem.'' (Algorithms based on
the ``elliptical curve discrete log problem'' are more resistant to
brute-force attacks and can use much smaller keys. In fact, they don't have
to be much larger than symmetric keys, as far as we know right now.)
Table 2: Key Lengths With Similar
Resistance to Brute-Force Attacks
Symmetric Key Length Public Key Length
56 bits 384 bits
64 bits 512 bits
80 bits 768 bits
112 bits 1792 bits
128 bits 2304 bits
Keys vs. Passphrases
A ``key'' is not the same thing as a ``passphrase'' or ``password.'' In
order to resist attack, all possible keys must be equally probable. If some
keys are more likely to be used than others, then an attacker can use this
information to reduce the work needed to break the cipher.
Essentially, the key must be random. However, a passphrase generally needs
to be easy to remember, so it has significantly less randomness than its
length suggests. For example, a 20-letter English phrase, rather than having
20 x 8 = 160 bits of randomness, only has about 20 x 2 = 40 bits of randomness.
So, most cryptographic software will convert a passphrase into a key through
a process called ``hashing'' or ``key initialization.'' Avoid cryptosystems
that skip this phase by using a password directly as a key.
Avoid anything that doesn't let you generate your own keys (e.g., the vendor
sends you keys in the mail, or keys are embedded in the copy of the software
Other factors that can influence the relative security of a product are
related to its environment. For example, in software-based encryption
packages, is there any plaintext that's written to disk (perhaps in
temporary files)? What about operating systems that have the ability to swap
processes out of memory on to disk? When something to be encrypted has its
plaintext counterpart deleted, is the extent of its deletion a standard
removal of its name from the directory contents, or has it been written
over? If it's been written over, how well has it been written over? Is that
level of security an issue for you? Are you storing cryptographic keys on a
multi-user machine? The likelihood of having your keys illicitly accessed is
much higher, if so. It's important to consider such things when trying to
decide how secure something you implement is (or isn't) going to be.
Snake Oil Warning Signs
``Trust Us, We Know What We're Doing''
Perhaps the biggest warning sign of all is the ``trust us, we know what
we're doing'' message that's either stated directly or implied by the
vendor. If the vendor is concerned about the security of their system after
describing exactly how it works, it is certainly worthless. Regardless of
whether or not they tell, smart people will be able to figure it out. The
bad guys after your secrets (especially if you are an especially attractive
target, such as a large company, bank, etc.) are not stupid. They will
figure out the flaws. If the vendor won't tell you exactly and clearly
what's going on inside, you can be sure that they're hiding something, and
that the only one to suffer as a result will be you, the customer.
If the vendor's description appears to be confusing nonsense, it may very
well be so, even to an expert in the field. One sign of technobabble is a
description which uses newly invented terms or trademarked terms without
actually explaining how the system works. Technobabble is a good way to
confuse a potential user and to mask the vendor's own lack of expertise.
And consider this: if the marketing material isn't clear, why expect the
instruction manual to be any better? Even the best product can be useless if
it isn't applied properly. If you can't understand what a vendor is saying,
you're probably better off finding something that makes more sense.
Avoid software which uses secret algorithms. This is not considered a safe
means of protecting data. If the vendor isn't confident that its encryption
method can withstand scrutiny, then you should be wary of trusting it.
A common excuse for not disclosing an algorithm is that ``hackers might try
to crack the program's security.'' While this may be a valid concern, it
should be noted that such ``hackers'' can reverse-engineer the program to
see how it works anyway. This is not a problem if the algorithm is strong
and the program is implemented properly.
Using a well-known trusted algorithm, providing technical notes explaining
the implementation, and making the source code available are signs that a
vendor is confident about its product's security. You can take the
implementation apart and test it yourself. Even if the algorithm is good, a
poor implementation will render a cryptography product completely useless.
However, a lock that attackers can't break even when they can see its
internal mechanisms is a strong lock indeed. Good cryptography is exactly
this kind of lock.
Note that a vendor who specializes in cryptography may have a proprietary
algorithm which they will reveal only under a non-disclosure agreement. The
crypto product may be perfectly adequate if the vendor is reputable. (But
how does a non-expert know if a vendor is reputable in cryptography?) In
general, you're best off avoiding secret algorithms.
Beware of any vendor who claims to have invented a ``new type of
cryptography'' or a ``revolutionary breakthrough.'' True breakthroughs are
likely to show up in research literature, and professionals in the field
typically won't trust them until after years of analysis, when they're not
so new anymore.
The strength of any encryption scheme is only proven by the test of time.
New crypto is like new pharmaceuticals, not new cars. And in some ways it's
worse: if a pharmaceutical company produces bogus drugs, people will start
getting sick, but if you're using bogus crypto, you probably won't have any
indication that your secrets aren't as secret as you think.
Avoid software which claims to use `new paradigms' of computing such as
cellular automata, neural nets, genetic algorithms, chaos theory, etc. Just
because software uses a different method of computation doesn't make it more
secure. (In fact, these techniques are the subject of ongoing cryptographic
research, and nobody has published successful results based on their use
Also be careful of specially modified versions of well-known algorithms.
This may intentionally or unintentionally weaken the cipher.
It's important to understand the difference between a new cipher and a new
product. Engaging in the practice of developing ciphers and cryptographic
products is a fine thing to do. However, to do both at the same time is
foolish. Many snake oil vendors brag about how they do this, despite the
lack of wisdom in such activity.
Experienced Security Experts, Rave Reviews, and Other Useless Certificates
Beware of any product that claims it was analyzed by ``experienced security
experts'' without providing references. Always look for the bibliography.
Any cipher that they're using should appear in a number of scholarly
references. If not, it's obviously not been tested well enough to prove or
disprove its security.
Don't rely on reviews in newspapers, magazines, or television shows, since
they generally don't have cryptographers to analyze software for them.
(Celebrity ``hackers'' who know telephone systems are not necessarily crypto
Just because a vendor is a well known company or the algorithm is patented
doesn't make it secure either.
Some vendors will claim their software is ``unbreakable.'' This is marketing
hype, and a common sign of snake oil. No algorithm is unbreakable. Even the
best algorithms are susceptible to brute-force attacks, though this can be
impractical if the key is large enough.
Some companies that claim unbreakability actually have serious reasons for
saying so. Unfortunately, these reasons generally depend on some narrow
definition of what it means to ``break'' security. For example, one-time
pads (see the next section) are technically unbreakable as far as secrecy
goes, but only if several difficult and important conditions are true. Even
then, they are trivially vulnerable to known plaintext attacks on the
message's integrity. Other systems may be unbreakable only if one of the
communicating devices (such as a laptop) isn't stolen. So be sure to find
out exactly what the ``unbreakable'' properties of the system are, and see
if the more breakable parts of the system also provide adequate security.
Often, less-experienced vendor representatives will roll their eyes and say,
``Of course it's not unbreakable if you do such-and-such.'' The point is
that the exact nature of ``such and such'' will vary from one product to
another. Pick the one that best matches your operational needs without
sacraficing your security requirements.
A vendor might claim the system uses a one-time-pad (OTP), which is provably
unbreakable. Technically, the encrypted output of an OTP system is equally
likely to decrypt to any same-size plaintext. For example,
598v *$_+~ xCtMB0
has an equal chance of decrypting to any of these:
the answer is yes
the answer is no!
you are a weenie!
Snake oil vendors will try to capitalize on the known strength of an OTP.
But it is important to understand that any variation in the implementation
means that it is not an OTP and has nowhere near the security of an OTP.
An OTP system works by having a ``pad'' of random bits in the possession of
both the sender and recipient, but absolutely no one else. Originally, paper
pads were used before general-purpose computers came into being. The pad
must be sent from one party to the other securely, such as in a locked
briefcase handcuffed to the carrier.
To encrypt an n -bit message, the next n bits in the pad are used as a key.
After the bits are used from the pad, they're destroyed, and can never be
The bits in the pad cannot be generated by an algorithm or cipher. They must
be truly random, using a real random source such as specialized hardware,
radioactive decay timings, etc. Some snake oil vendors will try to dance
around this issue, and talk about functions they perform on the bit stream,
things they do with the bit stream vs. the plaintext, or something similar.
But this still doesn't change the fact that anything that doesn't use real
random bits is not an OTP. The important part of an OTP is the source of the
bits, not what one does with them.
OTPs are seriously vulnerable if you ever reuse a pad. For instance, the
NSA's VENONA project , without the benefit of computer assistance,
managed to decrypt a series of KGB messages encrypted with faulty pads. It
doesn't take much work to crack a reused pad.
The real limitation to practical use of OTPs is the generation and
distribution of truly random keys. You have to distribute at least one bit
of key for every bit of data transmitted. So OTPs are awkward for general
purpose cryptography. They're only practical for extremely-low-bandwidth
communication channels where two parties can exchange pads with a method
different than they exchange messages. (It is rumored that a link from
Washington, D.C., to Moscow was encrypted with an OTP.)
Further, if pads are provided by a vendor, you cannot verify the quality of
the pads. How do you know the vendor isn't sending the same bits to
everyone? Keeping a copy for themselves? Or selling a copy to your rivals?
Also, some vendors may try to confuse random session keys or initialization
vectors with OTPs.
Algorithm or product X is insecure
Be wary of anything that claims that competing algorithms or products are
insecure without providing evidence for these claims. Sometimes attacks are
theoretical or impractical, requiring special circumstances or massive
computing power over many years, and it's easy to confuse a layman by
If there is a key-backup or key-escrow system, are you in control of the
backup or does someone else hold a copy of the key? Can a third party
recover your key without much trouble? Remember, you have no security
against someone who has your key.
If the vendor claims it can recover lost keys without using some type of
key-escrow service, avoid it. The security is obviously flawed.
Exportable from the USA
If the software is made in the USA, can it be exported? Strong cryptography
is considered dangerous munitions by the United States and requires approval
from the US Bureau of Export Administration, under the US Department of
Commerce, before it can leave the country. Various interested government
agencies serve as consultants to the Bureau of Export Administration when
evaluating such requests. (The U.S. isn't alone in this; some other nations
have similar export restrictions on strong cryptography.) Chances are, if
the software has been approved for export, the algorithm is weak or
If the vendor is unaware of export restrictions, avoid their software. For
example, if they claim that the IDEA cipher can be exported when most
vendors (and the US Government!) do not make such a claim, then the vendor
is probably lacking sufficient clue to provide you with good cryptography.
Because of export restrictions, some decent crypto products come in two
flavors: US-only and exportable. The exportable version will be crippled,
probably by using smaller keys, making it easy to crack.
There are no restrictions on importing crypto products into the US, so a
non-US vendor can legally offer a single, secure version of a product for
the entire world.
Note that a cryptosystem may not be exportable from the US even if it is
available outside the US: sometimes a utility is illegally exported and
posted on an overseas site.
Many crypto vendors claim their system is ``military grade.'' This is a
meaningless term, since there isn't a standard that defines ``military
grade,'' other than actually being used by various armed forces. Since these
organizations don't reveal what crypto they use, it isn't possible to prove
or disprove that something is ``military grade.''
Unfortunately, some good crypto products also use this term. Watch for this
in combination with other snake oil indicators, e.g., ``our military-grade
encryption system is exportable from the US!''
Avoid vendors who don't seem to understand anything described in the ``Basic
Concepts'' section above.
Avoid anything that allows someone with your copy of the software to access
files, data, etc. without needing some sort of key or passphrase.
Beware of products that are designed for a specific task, such as data
archiving, and have encryption as an additional feature. Typically, it's
better to use an encryption utility for encryption, rather than some tool
designed for another purpose that adds encryption as an afterthought.
No product is secure if used improperly. You can be the weakest link in the
chain if you use a product carelessly. Do not trust any product to be
foolproof, and be wary of any product that claims it is.
Interface isn't everything: user-friendliness is important, but be wary of
anything that puts too much emphasis on ease of use without due
consideration to cryptographic strength.
A procedure or mathematical formula. Cryptographic algorithms convert
plaintext to and from ciphertext.
Synonym for ``cryptographic algorithm''
To solve or ``break'' a cryptosystem.
Export Administration Regulations. The rules under which the export of
cryptographic software from the US are governed now.
A third party able to decrypt messages sent from one person to another.
Although this term is often used in connection with the US Government's
``Clipper'' proposals, it isn't limited to government-mandated ability
to access encrypted information at will. Some corporations might wish
to have their employees use cryptosystems with escrow features when
conducting the company's business, so the information can be retrieved
should the employee be unable to unlock it himself later, (if he were
to forget his passphrase, suddenly quit, get run over by a bus, etc.)
Or, someone might wish his spouse or lawyer to be able to recover
encrypted data, etc., in which case he could use a cryptosystem with an
One of the problems with encrypting such things as files in specific
formats (i.e., that of a word processor, email, etc.) is that there is
a high degree of predictability about the first bytes of the message.
This could be used to break the encrypted message easier than by brute
force. In ciphers where one block of data is used to influence the
ciphertext of the next (such as CBC), a random block of data is
encrypted and used as the first block of the encrypted message,
resulting in a less predictable ciphertext message. This random block
is known as the initialization vector. The decryption process also
performs the function of removing the first block, resulting in the
International Traffic in Arms Regulations. These are the rules by which
munitions, as defined by the US State Department, may (or may not) be
exported from the US. Until recently, this also included the export of
cryptography. The exportability of cryptography is now in the hands of
the Bureau of Export Administration, under the US Department of
A piece of data that, when fed to an algorithm along with ciphertext,
will yield plaintext. (Or, when fed to an algorithm along with
plaintext, will yield ciphertext.
random session key
This is a temporary key that is generated specifically for one message.
Typically, in public key cryptosystems, the message to be sent is
encrypted with a symmetric key that was specifically generated for that
message. The encrypted version of that message, as well as the
associated session key can then be encrypted with the recipient's
public key. When the recipient decrypts the message, then, the system
will actually decrypt the message it gets (which is the ciphertext
message and the symmetric key to decrypt it), and then use the
symmetric key to decrypt the ciphertext. The result is the plaintext
message. This is often done because of the tremendous difference in the
speed of symmetric vs. asymmetric ciphers.
1 B. Schneier. Applied Cryptography , 2e. John Wiley & Sons. 1996.
2 M. Blaze, W. Diffie, R. L. Rivest, B. Schneier, T. Shimomura, E.
Thompson, M. Wiener. ``Minimal Key Lengths for Symmetric Ciphers to
Provide Adequate Commercial Security''. Available at
3 The Crypt Cabal. Cryptography FAQ . Available at
4 The National Security Agency. The VENONA Project . Available at
5 RSA Data Security, Inc. 1997 Secret Key Challenge. Available at
Matt Curtin email@example.com http://www.interhack.net/people/cmcurtin/