Applied Cryptography Engineering

If you’re reading this, you’re probably a red-blooded American programmer with a simmering interest in cryptography. And my guess is your interest came from Bruce Schneier’s Applied Cryptography.

Applied Cryptography is a deservedly famous book that lies somewhere between survey, pop-sci advocacy, and almanac. It taught two generations of software developers everything they know about crypto. It’s literate, readable, and ambitious. What’s not to love?

Just this: as an instruction manual, Applied Cryptography is dreadful. Even Schneier seems to concede the point. This article was written with several goals: to hurry along the process of getting Applied Cryptography off the go-to stack of developer references, to point out the right book to replace it with, and to spell out what you else you need to know even after reading that replacement. Finally, I wrote this as a sort of open letter to Schneier and his co-authors.


Here’s an example of the problem with Applied Cryptography:

If simplicity and speed are your main concerns, ECB is the easiest and fastest mode to use a block cipher. It’s also the weakest. Besides being vulnerable to replay attacks, an algorithm in ECB mode is the easiest to cryptanalyze. I don’t recommend ECB for message encryption.

For encrypting random data, such as other keys, ECB is a good mode to use. Since the data is short and random, none of the shortcomings of ECB matter for this application.

To understand how dangerous this advice is, you need to understand block cipher modes. Most real-world encryption is based on block ciphers AES is a block cipher; so are DES and Blowfish. , which transform fixed-sized inputs into fixed-sized outputs. Since real-world inputs aren’t exactly 8 or 16 bytes wide, ciphers are adapted to them with a block mode.

Of the available block modes, ECB is the simplest to understand. It’s the mode you’d design yourself, the first time you confronted a block cipher: divide the input into blocks, and apply the cipher to each independently. ECB mode is so widespread that we call it “the default mode”.

What Applied Cryptography has to say about ECB technically correct Technically correct: not the best kind of correct in cryptography. at best, and outright wrong at worst. ECB is virtually never safe to use. It probably won’t make your ciphertext “easier to cryptanalyze”. Rather, it’s going to make it decryptable, by an attacker without the key, using a Perl script.


You should own Ferguson and Schneier’s follow-up, Cryptography Engineering (C.E.). Cryptography Engineering, used to be called Practical Cryptography. The two books are practically identical. Written partly in penance, the new book deftly handles material the older book stumbles over. C.E. wants to teach you the right way to work with cryptography without wasting time on GOST and El Gamal.

C.E. takes pains to teach which mode to use, raising the specter of ECB only to exorcise it before weighing the pros and cons of CBC and CTR. The book takes most of a chapter guiding readers to safe conclusions.

By contrast, along with a chart on the page that follows it, the excerpt above constitutes much of Applied Cryptography’s instruction on block modes. The book offers detailed coverage of DES, Lucifer, Madryga, NEWDES, FEAL, REDOC, LOKI, Khufu, RC2, IDEA, MMB, CA-1.1, Skipjack, GOST, CAST, Blowfish, SAFER, 3WAY, CRAB, SXAL8, and RC5. You will never need to know any of these. In fact, you’ll almost never “choose” ciphers at all: you’re going to choose AES, or the finalists of crypto competitions. But you’ll often need to choose cipher modes.

The biggest problem with Applied Cryptography isn’t the technical content, but the tone. It can’t decide whether to be a tour guide or a handbook. It’s fantastic pop science, but a dangerously broken textbook. Ever found an implementation of Needham-Schroeder using IDEA in ECB mode with digital signatures built on SNEFRU? The designer read Applied Cryptography. You can smell cryptosystems written by the book’s enthusiasts.

The tone of C.E. is sharply different. After reading it, you’re: (To their credit, Ferguson and Schneier seem equally intent on convincing people not to build bespoke crypto in the first place.)

  • going to use AES,
  • in CBC or CTR mode,
  • probably with random IVs,
  • with randomness from a real CSPRNG,
  • using HMAC-SHA2 to authenticate.

The best security books are the ones you can “read backwards” to learn how to attack systems instead of defending them. Cheswick and Bellovin’s Firewalls & Internet Security is like that; so is The Art Of Software Security Assessment. The first time I read C.E., I had the same feeling.

So I like Cryptography Engineering.


But of course, the important question about a book on crypto isn’t whether I like it.

Instead, you want to ask: could a competent developer read it, and, (…to the limit of what you could do with a book, of course) retaining everything, stand a chance at building a survivable cryptosystem?

I’m not sure. There are gaps in C.E.’s coverage. I’d like to lay those out now, in the hopes that a new edition (presumably to be called “Modern Cryptographic Design” so as to confuse us further) might spill some well-deserved ink on them.

2001-2003 was the tail end of the cryptographic dark ages, so let’s be clear that the book I’m criticizing was an achievement for its time. And its still the best guidebook to building crypto! That’s why I think it’s worth the time to dissect. “It’s all love”, as Stringer Bell might say.

Look at the highlight reel since the book was written: There were other advances, but C.E. did a good job presaging many of them.

  • Vaudenay’s CBC padding oracle attack, published just as the book was being written, racked up kills across pretty much every major web framework, including ASP.NET and Java.

  • Gregory Bard’s chosen-plaintext attack on TLS with predictable IVs was published and became the basis for Duong and Rizzo’s BEAST.

  • Osvik, Tromer, Percival, Bernstein, and a cast of thousands published the microarchitectural side channels, including cache timings that work over networks and local cache and branch buffer timings that threaten cloud hosted crypto.

  • Bleichenbacher’s e=3 signature bug in RSA validation broke Firefox.

  • Duong and Rizzo published the CRIME attack on TLS compression.

These attacks helped contribute new knowledge to the field. But many more attacks were published which, though known to the literature when C.E. was written, re-weighted the literature. A good example is the Playstation 3, which fell to repeated k-values in DSA signing.

Number Theoretic Crypto

C.E.’s coverage of RSA is weak enough that I think someone needs to write an article clarifying it. Nobody gets RSA right.

The thing to know about RSA is that it behaves differently from algorithms like AES. RSA ciphertexts are “just numbers” in a way that isn’t true with AES, and that makes RSA attacks subtler.

Lamentably, and despite the obvious effort Ferguson and Schneier sink into the math, they don’t nail the usage basics the way they do for AES. Encryption with RSA is counterintuitive: you need to go out of your way to feed it data that is as meaningless as possible. That’s the opposite of how a developer would think to use RSA. The authors don’t seem to expect readers to actually deploy RSA. If wishes were fishes!

A corrective article on C.E.’s RSA/DH coverage (or a new edition of C.E.) should teach developers:

  • About OAEP (for encryption) and PSS (for signing), the two safe ways to use RSA, and about the flaws of the default, PKCS #1 v1.5.

  • How numeric parameters are exploited in actual attacks (not just how to generate them safely).

  • How to safely validate RSA parameters and, in particular, how to safely generate and validate primes — a source of real-world RSA attacks.

  • A more conservative selection of parameters; for instance, it’s probably time to bury e=3 RSA.

Lastly: designers can trade flexibility for reduced complexity, and that’s usually a win. For instance, a crypto protocol can (and often should) hardcode parameters rather than negotiating them. Little mention is made of that opportunity in C.E. Too bad. The conservative approach is again counterintuitive to developers, to whom hardcoding anything is like simony.

Missing Basic Algorithms

The authors take the general tack of not describing constructions they don’t like. The problem is, patented or not, some of the excluded schemes see widespread use.

SRP is a great example. SRP establishes keys between a client and a server using only a password, and authenticates that password without revealing it. That’s simply too useful a capability for developers not to use. Being morally similar to DH, SRP inherits many of its pitfalls: we routinely defeat several SRP implementations by coercing servers to zero out key computations.

A more troublesome omission is DSA. DSA is a cryptographic signing algorithm; it’s used to authenticate binaries, or to sign Diffie Hellman exchanges for secure channels with forward secrecy. It’s both popular and very tricky, as the authors of the Playstation 3 signing code might tell you. DSA seems like a case where even if you decide not to cover it, you’d probably want to add strongly-worded language about how dangerous it is to play with. No such warning is to be found in this book.

Elliptic Curve

Elliptic curve cryptography (ECC) is similar in spirit to basic number-theoretic cryptography, but in a different, harder mathematical group. ECC keys are smaller, offering better security per key bit spent.

C.E. entire coverage of ECC is the single clause “such as those used in elliptic curve” (and note that clause isn’t even specific to ECC; zero points awarded).

ECC is going to replace RSA within the next 10 years. New systems probably shouldn’t use RSA at all. The basic finite field groups used by RSA and Diffie Hellman are looking less and less safe (see Joux, or Eran Tromer’s hypothesized 1024-bit RSA cracker with its measly $1MM price tag).

Conventional wisdom has ECC being notoriously tricky. And, for extra fun, ECC constructions inherit the implementation traps of DH and DSA. Developers need lots of help with it. It’s downright weird for the best modern crypto book to exclude ECC.

Encrypt-then-MAC

Imagine being lectured You always need to do both, encrypt and MAC, and a grateful nation thanks Ferguson and Schneier for making that clear. by Wallace Shawn’s character from The Princess Bride on the phlogiston theory of combustion. That’s a little bit like what it’s like to learn the proper order of encryption and authentication from C.E. We know today that you want to encrypt, then authenticate; to do otherwise is to invoke Moxie Marlinspike’s Cryptographic Doom Principle. But even though encrypt-then-MAC had been proven secure when C.E. was first written, the authors aren’t so sure, and attempt to “teach the controversy”.

For the flavor of how improvident that coverage turns out to be, see HTTPS/TLS. Every modern TLS stack offers AES encryption. But many of the largest, savviest sites in the world prefer instead RC4, a comically broken stream cipher obsoleted half a decade before Ferguson and Schneier’s book was printed. Why? Because HTTPS/TLS is from the phlogiston era of cryptography and uses AES in a MAC-then-encrypt construction, resulting in an intractable timing vulnerability.

Stream Encryption

A very careful reader can probably deploy stream encryption from C.E. recommendations and survive. But the coverage is imperfect; for instance:

As with OFB mode, you must make absolutely sure never to reuse a single key/nonce combination. This is a disadvantage that is often mentioned for CTR, but CBC has exactly the same problem. If you use the same IV twice, you start leaking data about the plaintexts. CBC is a bit more robust, as it is more likely to limit the amount of information leaked.

The equivalence drawn between CTR nonces and CBC IVs is crazymaking. CBC does not have exactly the same problem as CTR; it has a very different problem. CTR nonces must never repeat. CBC IVs must not be predictable. Screw up a CTR nonce and your system is breakable offline with a pencil and paper; do the same with CBC and you’ve enabled online attacks with attacker-controlled plaintext.

C.E. lacks any coverage on native stream ciphers, such as the ones judged by the eSTREAM competition. There’s a rich literature on native stream ciphers, and C.E. doesn’t help developers make use of it.

The book also misses an opportunity to teach combined authenticated encryption (AEAD) modes. The AEAD modes combine stream cipher modes with MAC constructions that developers don’t have to think about. They’re a little magical, in the same sense that ABS brakes were magical in the 1970s.

While C.E. discusses some of the AEAD modes, the emphasis is on their downsides. The authors would clearly rather have developers bolt on HMAC-SHA2 manually, which is a shame; the track record on that construction isn’t great.

Key Derivation

The sad fact is that developers think cryptographic keys are a kind of password. Crypto code in the field is littered with hardcoded ASCII strings used as keys. If you’re going to know just one thing about cryptography, make it this: crypto keys are cryptographically random.

But users must be able to interact with cryptosystems. As a rule, they can’t remember 128 bit random numbers. And so real cryptosystems will occasionally need to accept passphrases.

Meanwhile, the single most widespread application of cryptography in modern software development is password storage. Virtually every online application in the world deals with this problem, and most of them apply crypto (badly).

When C.E. was written In the past several years, the literature on KDFs has taken on much greater importance as GPU programming has begun demonstrating how bad weak KDFs are. The best illustration of that are the GPU password crackers, which largely defeat the “salted hash” constructions most applications use to protect passwords. , there were two mainstream key derivation functions (KDFs) available for transmuting passphrases into crypto keys: bcrypt, based on the authors’ own Blowfish algorithm, and PBKDF2, the hash-based PKCS #5 v2.0 standard. Both constructions have the advantage of incurring a very small time penalty from legitimate users while extracting an enormous penalty from attackers. In the years since the book was written, we’ve also learned about “memory-hard” KDFs, of which scrypt is the seminal example, which are designed to be difficult to scale attacks against even with custom silicon.

Defense of user passwords is important enough to merit coverage in the book. Every developer needs to know how. But the topic is even more important in the more complicated cryptosystems C.E. contemplates. A real-world cryptosystem can get every other detail right and still manage to be merely as strong as a 1990s Unix password file if its keys come from a poor KDF.

Side Channels

In computer security, a covert channel is a hidden signaling mechanism. Attackers exploit covert channels to leak messages across security boundaries (for instance in a pattern of specially-encoded DNS queries.) . Side channels are the flip side of covert channels; they’re actual signaling performed unexpectedly.

One of the first things every software developer learns how to do is comparing strings. Developers don’t think before writing code to do string compares; many of them have known how since they were 11 years old. But the way you learned to compare strings when you were 11 doesn’t work with crypto secrets. Because the algorithm stops at the first mismatched character, it leaks timing information.

Timing attacks Here’s the exploit: Build a string you want to forge. Giving it an all-zeroes HMAC. Then send thousands of variants of the string and HMAC with the first byte randomized, and measuring each variant for the time it takes to get a response. The variant that takes the longest on average is probably the correct first byte. Lather, rinse, repeat. are pernicious, but they aren’t the most commonly exploited side channels. That honor belongs to protocol errors.

The best example of a protocol error side channel is the padding oracle. Ciphertexts are typically padded to block boundaries. Receivers check the padding after decryption and strip it off. If the padding is invalid, the system coughs up an error, and with it the ability to decrypt messages without keys. The validity of the padding tips the attacker off about the plaintext value of a selected byte.

There are other error oracles besides the block padding oracle. Several affect RSA. Variants of the attack affect some stream cipher modes. An error oracle coupled with known plaintext broke SIM card encryption. A book on safe crypto should give special coverage to error and exception handling.

The most counterintuitive example of a side channel attack I know of is Duong and Rizzo’s CRIME attack on TLS. Ask Applied Cryptography about compression and it’ll tell you:

Using a data compression algorithm together with an encryption algorithm makes sense for two reasons: Cryptanalysis relies on exploiting redundancies in the plaintext; compressing a file before encryption reduces these redundancies. Encryption is time-consuming; compressing a file before encryption speeds up the entire process.

It turns out, no. The length of the messages in a cryptosystem is also a potential side channel. If attackers control plaintext, they can submit inputs that can be correlated with message lengths to probe for the existence of string prefixes; longer messages tell the attacker their guess was wrong, while shorter messages indicate a redundancy that compression could exploit, betraying the presence of the prefix. Attackers can decrypt whole messages this way.

Want more examples? Consider cloud hosting, probably the de facto standard deployment environment for most new crypto. Cloud applications share metal with strangers, and thus attackers, who will gladly spend $40 to co-host themselves with a target.

It turns out that the microarchitecture of a typical CPU (that is, the design details of that CPU that aren’t immediately evident in the instruction set) is riddled with side channels. An attacker on the same machine as their victim can write a program that constantly monitors the CPU caches, producing a trace that can be correlated with crypto operations the attacker requests of that victim. It’s hard even to know where all these caches are; for instance, modern CPU performance relies on branch prediction, which uses its own obscure caches to hold branch targets.

Cryptography Engineering provides some background information on side channels, then throws up its hands and declares side channels to be an “arms race” without providing in-depth coverage. This would be a nit if the specifics of side channels didn’t have so many specific and durable consequences:

  • Developers should choose mature crypto libraries that have been audited for side channel defects.

  • Developers should be extraordinarily cautious both with error messages and, more importantly, with handling exceptional cases in message decryption.

  • Developers shouldn’t compress plaintext before encrypting.

  • Developers should be wary of hosting crypto code on shared hardware, or of offering sensitive crypto tools on platforms which might also host attacker code even at lower privilege levels.

Simply put, side channels want their own chapter in C.E.

Browsers, TLS, and The Rest

Finally, some points that are less about criticizing C.E. and more about establishing how useful a new edition could be:

  • HTTPS/TLS Frankly, Schneier doesn’t have much of an excuse for not covering TLS; he’s the co-author, with Dave Wagner, of one of the better-known security analyses of SSL 3.0 (the basis for TLS). Word of advice: get Wagner to co-author the next version! is the cryptosystem developers are most likely to come into contact with. It’s not foolproof; you have to make choices to deploy it. What ciphersuites should you use? What is perfect forward secrecy and what’s the impact of using it? How does session resumption work and what impact does it have on your systems security?

  • I am beating my own dead hobbyhorse by saying this, but I also think a discussion of the perils of browser Javascript cryptography would be worthwhile. It’s a bad idea that is unlikely to get less popular on its own.

  • Even if the authors are unwilling to delve into Javascript, the interactions between HTTPS and the HTTP Same Origin Policy (the most important security policy on the Internet) should be worth at least a couple of paragraphs.


I obviously couldn’t have written a better book than Cryptography Engineering. I doubt many other people could either. While we could use more books about attacking crypto, we need one good one, kept up to date, on building crypto. Cryptography Engineering should be that book.

If this stuff is interesting to you, here’s some additional reading:

  • It should be unlawful to use RSA without reading 20 Years Of Attacks On RSA; Boneh’s paper won’t get you up to date, but it’ll give you a good idea what you’re up against.

  • A good starting point on encrypt-then-MAC is Read everything else on Marlinspike’s and Langley’s blogs, too. (again) Moxie Marlinspike’s Cryptographic Doom Principle. To see the interplay between cryptographic doom and side channels, read Adam Langley’s Lucky 13 Attacks on TLS-CBC; pay attention towards the end at what a cast-iron bitch it is to try to lock down badly-designed constructions against side channels.

  • Watch Nate Lawson’s talk on exploiting timing attacks. Too many developers think of side channels as an abstract threat. And too many of the ones that don’t see timing attacks everywhere, even where they aren’t.

  • Ross Anderson and Serge Vaudanay’s Minding Your P’s And Q’s is the best introduction to parameter flaws in number-theoretic crypto like RSA and DSA.

  • For a scary story to tell young developers before they go to sleep at night, read Tromer and Osvik’s AES cache timing paper, and then reconsider cloud crypto.

  • Finally, if you’re interested in ECC crypto, the best place to start is Bernstein, Lange, and Schwabe’s NaCl library. NaCl was carefully designed so that developers can pick it up and use it today without creating low-level crypto vulnerabilities.

Thanks to Marsh Ray, Nate Lawson, Matthew Green, Sean Devlin, Tony Arcieri, and Hans Nielsen for reading drafts of this.