How to choose your secure messaging app

Since WhatsApp announced its acquisition, a lot of people started to switch to alternatives, trying to escape from Facebook. Some of them then discovered my article about Telegram, and a common answer was “hey, at least, it is better than WhatsApp, because it is open source, faster and it has encryption”.

This is a very bad way to decide what application you should use. If you choose a secure messaging app, it must be because you need it, not just because you want to avoid Facebook.

Those are not good enough requirements:

  • independent from Facebook
  • fast
  • multi platforms
  • open source

Yes, even open source, because it does not magically make software safe.

So, what are goods requirements? Well, I already have a list of what a secure messaging app should meet to be considered. If an app does not follow those requirements, it may not be a good idea to use it.

But it still does not mean the app will fit your use case. So you must define your use case:

  • Why do you need it?
  • With whom will you communicate?
  • Who is the adversary?
  • What will happen if some of your information is revealed to the adversary?
  • Does it need to be always available?
  • For how long will it be used?

This is part of what I mean when I insist on having a threat model: you cannot choose correctly if you do not know the risks.

Here are a few examples that you could consider.

The activist in a protest

The activist must be able to communicate quickly in the crowd. Identifying info might not be the most important part, because she can use burner phones (phones that will be abandoned after the protest). The most important feature is that it should be always available. Phone networks were often used to disrupt activist communication, so a way to send message through WiFi our bluetooth might be useful. The messages can be sent to a lot of different people, so being able to identify them might be important. If it is large enough to be infiltrated easily, then having no way to identify people is crucial.

Being able to send photos is important, because they might be the only proof of what happened in the protest. Here, I have in mind the excellent ObscuraCam app, which is able to quickly hide the faces of people in photos before sending them.

The application should not keep logs, or provide a way to quickly delete them, or encrypt them by default, because once someone is caught, the police will look through the phone.

The crypto algorithms and protocols should be safe and proven for that use case, because the adversaries will have the resources to exploit any flaw.

No need for a good update system if the devices will be destroyed after use.

The employee of a company with confidential projects

The adversaries here are other companies, or even other countries. The most important practice here is the “need to know”: reduce the number of persons knowing the confidential information. that means the persons communicating between themselves is reduced, and you can expect that they have a mean of exchanging information securely (example: to verify a public key).

Identifying who talks with whom is not really dangerous, because it is easy to track the different groups in a company. You may be confident enough that the reduced group will not be infiltrated by the adversary. The messages should be stored, and ideally be searchable. File exchange should be present.

There could be some kind of escrow system, to reveal information if you have a certain access level. Authentication is a crucial point.

The crypto may be funnier for that case, because the flexibility needed can be provided by some systems, like identity based encryption.Enterprise policies might be able to force regular uodates of the system, so that everybody has the same protocol version at the ame time, and any eventual flaw will be patched quickly.

The common user

It is you, me, anyone wanting to exchange private messages with friends or family. Here, trying to protect against the NSA is futile, because most of the contacts might not have the training needed. Trying to hide the contacts list from Facebook is futile too: even if someone protects the information, one of the contacts may not. The adversary you should consider here: crooks, pirates, anyone that could exploit the private messages for criminal ways (stealing bank info, blakcmailing, sending malware, etc).

An application fitting this use case should encrypt messages, preferably end to end, to limit problems when the exchange server is compromised. The service might not provide any expectation of anonymity. Messages should be stored, but encrypting them is a good option, in case the device is lost or stolen.

The crypto does not need to be very advanced, but it should use common, well known designs.

There should be a good update system, a way to negotiate protocol versions (and forbid some unsafe versions), because you will never be sure that everybody has performed all the needed updates.

Your use case here

Those were some common situations, for which some solutions exist, but there are a lot more possible use cases. If you are not sure about yours and need help defining your threat model, do not hesitate to ask for help, and do not jump on a solution because the marketing material says it is safe.

A good security solution will not only tell you what is protected, and how, but also what is not protected, and the security margins you have. It will also teach you the discipline you need to apply to get the most out of it.


The problem with meritocracy

Everytime people discuss the hacker community and its diversity, I see someone waving the “meritocracy” argument. “It is not our fault those minorities are not well represented, if they knew more stuff or did more stuff, they would have a better status”.

It is easy to see how that argument would be flawed, as meritocracy is a power structure, and whenever a power structure is created, after some time it tends to reinforce its own community. But that is not my point right now.

I realized that the idea of meritocracy is so deeply ingrained in the hacker mindset that we lost sight of what was important. I can see how that idea is appealing. Once you prove you know stuff, people will recognize you, and that will be enough to motivate you to learn. Except it is not. The meritocracy is just another way to exclude people. Once you consider someone’s status by how much you perceive they know, things go downhill.

Some are good at faking knowledge. Some know their craft, but do not talk that well. Some are not experts, but have good ideas. Some would like to learn without being judged. Everytime you dismiss someone’s opinion because of their apparent (lack of) knowledge, everytime you favor someone’s opinion because of their apparent knowledge, you are being unscientific and unwelcoming. You are not a hacker, you are just a jerk.

Somewhere along the way, people got too hung up on meritocracy, and forgot that you hack for knowledge and for fun, not for status. It is all about testing stuff, learning, sharing what you learned, discussing ideas and helping others do the same, whatever their skills or their experience. Status and power structures should have nothing to do with that.

Guess what? I pointed out that bad behaviour, but I am guilty of it too. I have to constantly keep myself in check, to avoid judging people instead of judging ideas. That’s alright. Doing the right thing always requires some effort.

Telegram, AKA “Stand back, we have Math PhDs!”

Disclaimer: this post is now very old and may not reflect the current state of Telegram’s protocol. There has been other research in the meantime, and this post should not be used for your choice of secure messaging app. That said, on a personal note, I still think Telegram’s cryptosystem is weird, and its justifications are fallacious. If you want a recommendation on secure messaging apps: use a system based on the Axolotl/Signal protocol. It is well designed and has been audited. Signal and WhatsApp are both using that protocol, and there are others.

Here is the second entry in our serie about weird encryption apps, about Telegram, which got some press recently.

According to their website, Telegram is “cloud based and heavily encrypted”. How secure is it?

Very secure. We are based on a new protocol, MTProto, built by our own specialists, employing time-tested security algorithms. At this moment, the biggest security threat to your Telegram messages is your mother reading over your shoulder. We took care of the rest.

(from their FAQ)

Yup. Very secure, they said it.

So, let’s take a look around.

Available technical information

Their website details the protocol. They could have added some diagrams, instead of text-only, but that’s still readable. There is also an open source Java implementation of their protocol. That’s a good point.

About the team (yes, I know, I said I would not do ad hominem attacks, but they insist on that point):

The team behind Telegram, led by Nikolai Durov, consists of six ACM champions, half of them Ph.Ds in math. It took them about two years to roll out the current version of MTProto. Names and degrees may indeed not mean as much in some fields as they do in others, but this protocol is the result of thougtful and prolonged work of professionals

(Seen on Hacker News)

They are not cryptographers, but they have some background in maths. Great!

So, what is the system’s architecture? Basically, a few servers everywhere in the world, routing messages between clients. Authentication is only done between the client and the server, not between clients communicating with each other. Encryption happens between the client and the server, but not using TLS (some home made protocol instead). Encryption can happen end to end between clients, but there is no authentication, so the server can perform a MITM attack.

Basically, their threat model is a simple “trust the server”. What goes around the network may be safely encrypted, although we don’t know anything about their server to server communication, nor about their data storage system. But whatever goes through the server is available in clear. By today’s standards, that’s boring, unsafe and careless. For equivalent systems, see Lavabit or iMessage. They will not protect your messages against law enforcement eavesdropping or server compromise. Worse: you cannot detect MITM between you and your peers.

I could stop there, but that would not be fun. The juicy bits are in the crypto design. The ideas are not wrong per se, but the algorithm choices are weird and unsafe, and they take the most complicated route for everything.

Network protocol

The protocol has two phases: the key exchange and the communication.

The key exchange registers a device to the server. They wrote a custom protocol for that, because TLS was too slow and complicated. That’s true, TLS needs two roundtrips between the client and the server to exchange a key. It also needs x509 certificates, and a combination of a public key algorithm like RSA or DSA, and eventually a key exchange algorithm like Diffie-Hellman.

Telegram greatly simplified the exchange by requiring three roundtrips, using RSA, AES-IGE (some weird mode that nobody uses), and Diffie-Hellman, along with a proof of work (the client has to factor a number, probably a DoS protection). Also, they employ some home made function to generate the AES key and IV from nonces generated by the server and the client (server_nonce appears in plaintext during the communication):

  • key = SHA1(new_nonce + server_nonce) + substr (SHA1(server_nonce + new_nonce), 0, 12);
  • IV = substr (SHA1(server_nonce + new_nonce), 12, 8) + SHA1(new_nonce + new_nonce) + substr (new_nonce, 0, 4);

Note that AES-IGE is not an authenticated encryption mode. So they verify the integrity. By using plain SHA1 (nope, not a real MAC) on the plaintext. And encrypting the hash along with the plaintext (yup, pseudoMAC-Then-Encrypt).

The final DH exchange creates the authorization key that will be stored (probably in plaintext) on the client and the server.

I really don’t understand why they needed such a complicated protocol. They could have made something like: the client generates a key pair, encrypts the public key with the server’s public key, sends it to the server with a nonce, and the server sends back the nonce encrypted with the client’s public key. Simple and easy. And this would have provided public keys for the clients, for end-to-end authentication.

About the communication phase: they use some combination of server salt, message id and message sequence number to prevent replay attacks. Interestingly, they have a message key, made of the 128 lower order bits of the SHA1 of the message. That message key transits in plaintext, so if you know the message headers, there is probably some nice info leak there.

The AES key (still in IGE mode) used for message encryption is generated like this:

The algorithm for computing aes_key and aes_iv from auth_key and msg_key is as follows:

  • sha1_a = SHA1 (msg_key + substr (auth_key, x, 32));
  • sha1_b = SHA1 (substr (auth_key, 32+x, 16) + msg_key + substr (auth_key, 48+x, 16));
  • sha1_с = SHA1 (substr (auth_key, 64+x, 32) + msg_key);
  • sha1_d = SHA1 (msg_key + substr (auth_key, 96+x, 32));
  • aes_key = substr (sha1_a, 0, 8) + substr (sha1_b, 8, 12) + substr (sha1_c, 4, 12);
  • aes_iv = substr (sha1_a, 8, 12) + substr (sha1_b, 0, 8) + substr (sha1_c, 16, 4) + substr (sha1_d, 0, 8);

where x = 0 for messages from client to server and x = 8 for those from server to client.

Since the auth_key is permanent, and the message key only depends on the server salt (living 24h), the session (probably permanent, can be forgotten by the server) and the beginning of the message, the message key may be the same for a potentially large number of messages. Yes, a lot of messages will probably share the same AES key and IV.

Edit: Following Telegram’s comment, the AES key and IV will be different for every message. Still, they depend on the content of the message, and that is a very bad design. Keys and initialization vectors should always be generated from a CSPRNG, independent from the encrypted content.

Edit 2: the new protocol diagram makes it clear that the key is generated by a weak KDF from the auth key and some data transmitted as plaintext. There should be some nice statistical analysis to do there.

Edit 3: Well, if you send the same message twice (in a day, since the server salt lives 24h), the key and IV will be the same, and the ciphertext will be the same too. This is a real flaw, that is usually fixed by changing IVs regularly (even broken protocols like WEP do it) and changing keys regularly (cf Forward Secrecy in TLS or OTR). The unencrypted message contains a (time-dependent) message ID and sequence number that are incremented, and the client won’t accept replayed messages, or too old message IDs.

Edit 4: Someone found a flaw in the end to end secret chat. The key generated from the Diffie-Hellman exchange was combined with a server-provided nonce: key = (pow(g_a, b) mod dh_prime) xor nonce. With that, the server can perform a MITM on the connection and generate the same key for both peers by manipulating the nonce, thus defeating the key verification. Telegram has updated their protocol description and will fix the flaw. (That nonce was introduced to fix RNG issues on mobile devices).

Seriously, I have never seen anyone use the MAC to generate the encryption key. Even if I wanted to put a backdoor in a protocol, I would not make it so evident…

To sum it up: avoid at all costs. There are no new ideas, and they add their flawed homegrown mix of RSA, AES-IGE, plain SHA1 integrity verification, MAC-Then-Encrypt, and a custom KDF. Instead of Telegram, you should use well known and audited protocols, like OTR (usable in IRC, Jabber) or the Axolotl key ratcheting of TextSecure.

SafeChat, P2P encrypted messages?

For the first article in the new post serie about “let’s pick apart the new kickstarted secure decentralized software of the week”, I chose SafeChat, which started just two days ago. Yes, I like to hunt young preys :p

A note, before we begin: this analysis is based on publicly available information at the time of writing. If the authors of the project give more information, I can update the article to match it. The goal is to assert, with what little we know about the project, if it is a good idea to give money to this project. I will only concentrate on the technical parts, not on the team itself (even if, for some of those projects, I think they’re idiots running with scissors in hand).

What is SafeChat?

Open source encryption based instant messaging software

SafeChat is a brilliantly simple deeply secure instant messaging system for mobile phones and computers

SafeChat is an instant messaging software designed by Commercial Free. There is no real indication about who really works there, and where the company is based, except for David Crawford, who created the Kickstarter project and is based in Montreal in Canada.

Note that SafeChat is only a small part of the services they want to provide. Commercial Free will also have plans including an email encryption service (no info about that one) and cloud storage.

Available technical information

There is not much to see. They say they are almost done with the core code, but the only thing they present is some videos of what the interaction with the app could be.

Apparently, it is an instant messaging application with Android and iOS applications and some server components.  Session keys are generated for the communication between users. They will manage the server component, and the service will be available with a yearly subscription.

It seems they don’t want to release much information about the cryptographic components they use. They talk about “peer to peer encryption” (lol) which is open source and standard. If anyone understands what algorithm or protocol they refer to, please enlighten me. They also say they will mix in some proprietary code (so much for open source).

I especially like the part about NIST. They mock NIST, telling that they have thrown “all standard encryption commonly used today out the window”. I am still wondering what “open source and standard peer to peer encryption” means.

Network protocol

The iOS and Android applications will apparently provide direct communication between users. I guess that from their emphasis on P2P, but also from the price they claim: $10 per user per year would be a bit small to pay for server costs if they had to route all the messages.

P2P communication between phones is technically feasible. They would probably need to implement some TCP hole punching in their solution, but it is doable.

Looking athe the video, it seems there is a key agreement before communication. I do not really like the interaction they chose to represent key agreement (with the colors and the smileys). There are too many different states, while  people only need to know “are we safe now?”

I am not sure if there is a presence protocol. The video does not really show it. If there is no presence system, are messages stored until the person is online? Stored on the server or on the client? Does the server notify the client when the person becomes available?


By bringing together existing theories of cryptography and some proprietary code to bind them together, we are making a deeply encrypted private chatting system that continues to evolve as the field of cryptography does.

Yup, I really feel safe now.

Joke aside, here is what we can guess:

  • session keys for the communication between users. I don’t know if it is a Diffie-Hellman based protocol
  • no rekeying, ie no perfect forward secrecy
  • no info on message authentication or integrity verification
  • I am not sure if the app generates some asymmetric keys for authentication, if there is trust on first use, or whatever else
  • the server might not be very safe, because they really, really want to rely on German laws to protect it. If the crypto was fully managed client side, they would not care about servers taken down, they could just pop another somewhere.

There could be a PKI managed by Commercial Free. That would be consistent with the subscription model (short lived certificates is an easy way of limiting the usage of a service).

Threat model

Now, we can draw the rough threat model they are using:

What we want to do is make it impractical for an organization to snoop your communications as it would become very hard to find them and then harder still to decrypt them.

Pro tip: a system with a central server does not make it hard to find communications.

Attacker types:

  • phone thief: I don’t think they use client side encryption for credentials and logs. Phone thiefs and forensics engineers won’t have a real problem there
  • network operator: they can disrupt the communication, but will probably not be able to decrypt or do MITM (I really think the server is managing the authentication part, along with setting up the communication)
  • law enforcement: they want to rely on German laws to protect their system. At the same time, they do not say they will move out to Germany to operate the system. If they stay in Canada, that changes the legal part. If they use a certificate authority, protecting the server will be useless, because they can just ask the key at the company.
  • server attacker: the server will probably be Windows based (see the core developer’s skills). Since that design is really server centric, taking down the server might take down the whole service. And attacking it will reveal lots of interesting metadata, and probably offer MITM capabilities
  • nation state: please, stop joking…


Really, nothing interesting here. I do not see any reason to give money to this project: there is nothing new, it does not solve big problems like anonymous messaging, or staying reliable if one server is down. Worse, it is probably possible to perform a MITM attack if you manage the server. Nowadays, if you create a cryptographic protocol with client side encryption, you must make sure that your security is based on the client, not the server.

Alternatives to this service:

  • Apple iMessage: closed source, only for iOS, encrypted message, MITM is permitted for Apple by the protocol, but “we have not architected the server for this”. Already available.
  • Text Secure by OpenWhisperSystems: open source, available for iOS and Android, uses SMS as a transport protocol, uses OTR (Off the Record protocol) to protect the communication, no server component. Choose Text Secure! It is really easy to use, and OTR is well integrated in the interface.

My ideal job posting

This post is a translation of something I wrote in French for Human Coders. They asked me what would be the ideal job post from a developer’s standpoint:

How whould you write a job announcement attracting good developers? Most recruiters complain that finding the right candidates is an ordeal.

If you ask me, it is due to very old recruitment practices: writing job posts for paper ads (where you pay by the letter), spamming them to as many people as possible, mandating fishy head hunters… This has worked in the past, but things changed. A lot more companies are competing to recruit developers, and many more developers are available, so separating the wheat from the chaff is harder.

We can do better! Let’s start from scratch. For most candidates, a job posting is the first contact they’ll have with your company. It must be attrctive, exciting! When I read “the company X is the leader on the market of Y”, I don’t think that they’re awesome, I just wonder what they really do.

A job posting is a marketing document. Its purpose is not to filter candidates, but to attract them! And how do you write a marketing document?

YOU. TALK. ABOUT. THE. CLIENT. You talk about his problems, his aspirations, and only then, will you tell him how you will make things better for him. For a job posting, you must do the same. You talk to THE candidate. Not to multiple candidates, not to the head hunter or the HR department, but to the candidate. Talk about the candidate, and only the candidate. When a developer looks for a job, she doesn’t want to “work on your backend application” or “maintain the web server”. That is what she will do for you. This is what she wants:

  • getting paid to write code
  • work on interesting technologies
  • a nice workplace atmosphere
  • learn
  • etc.

A good job posting should answer the candidate’s aspirations, and talk about the carrer path. Dos this job lead to project management? Do you propose in-house training? Is there a career path for expertise in your caompany?

Do you share values with your candidate? I do not mean the values written by your sales team and displayed on the “our values” page of your website. I am talking about the values of the team where the candidate will end up. Do they work in pair programming? Do they apply test driven development? There is no best way to work, the job can be done in many ways, so you must make sure that the candidate will fit right in.

What problem are you trying to solve with your company? Do you create websites that can be managed by anyone? Do you provide secure hosting? Whatever your goal is, talk about it instead of taliking about the product. I do not want to read, “our company develops a mobile server monitoring tool”, because that is uninteresting. If I read “we spent a lot of time on call for diverse companies, so we understood that mobility is crucial for some system administrators, so we created a tool tailored for moving system administrators”, I see a real problem, a motivation to work, a culture that I could identify to.

By talking that way to the candidate, you will filter candidates on motivation and culture instead of filtering on skills. That can be done later, once you see the candidate You did not really think that a resume was a good way to select skilled people, do you?

Here is a good example of fictive job posting, from a company aggregating news for developers, looking for a Rails developer:

“You are a passionnate Ruby on Rails developers, you are proiud of you unit tests, and you enjoy the availability of Heroku’s services? That’s the same for us!

At Company X, we love developers: all of our services are meant for their fulfillment. We propose a news website about various technologies, higly interesting trainings and a job board for startups.

Our employees benefit fully from these services, and make talks in conferences all around France. By directly talking with other developers, they quickly get an extensive knowledge of current technologies.

Our news website is growing fast, so we need help to scale it. The web app uses Heroku and MongoDB, with a CoffeeScript front end. Are you well versed in Rails optimization? If yes, we would love to talk with you!”

Note that I did not talk about years of experience, or a city. I want to hire a Rails developer, not necessarily a french developer. I want someone with experience in optimization, not someone over 27.

With such a job posting, you will receive a lot more interesting employment applications. Now, are you afraid that it will incur a lot more work? The solution in a future post: how to target candidates efficiently? Get away from job boards!

HN Discuss on Hacker News

5 easy tips to accelerate SSL

Photo credit: TheKenChan -

Update: following popular demand, the article now includes nginx commands 🙂

Update 2: thanks to jackalope from Hacker News, I added a missing Apache directive for the cipher suites.

Update 3: recent attacks on RC4 have definitely made it a bad choice, and ECDHE cipher suites got improvements.

SSL is slow. These cryptographic algorithms eat the CPU, there is too much traffic, it is too hard to deploy correctly. SSL is slow. Isn’t it?


SSL looks slow, because you did not even try to optimize it! For that matter, I could say that HTTP is too verbose, XML web services are verbose too, and all this traffic makes the website slow. But, SSL can be optimized, as well as everything!

Slow cryptographic algorithms

The cryptographic algorithms used in SSL are not all created equal: some provide better security, some are faster. So, you should choose carefully which algorithm suite you will use.

The default one for Apache 2’s SSLCipherSuite directive is: ALL: !ADH:RC4+RSA:+HIGH:+MEDIUM:+LOW:+SSLv2:+EXP

You can translate that to a readable list of algorithms with this command: openssl ciphers -v ‘ALL:!ADH:RC4+RSA:+HIGH:+MEDIUM:+LOW:+SSLv2:+EXP’

Here is the result:

DHE-RSA-AES256-SHA      SSLv3 Kx=DH       Au=RSA  Enc=AES(256)  Mac=SHA1
DHE-DSS-AES256-SHA      SSLv3 Kx=DH       Au=DSS  Enc=AES(256)  Mac=SHA1
AES256-SHA              SSLv3 Kx=RSA      Au=RSA  Enc=AES(256)  Mac=SHA1
DHE-RSA-AES128-SHA      SSLv3 Kx=DH       Au=RSA  Enc=AES(128)  Mac=SHA1
DHE-DSS-AES128-SHA      SSLv3 Kx=DH       Au=DSS  Enc=AES(128)  Mac=SHA1
AES128-SHA              SSLv3 Kx=RSA      Au=RSA  Enc=AES(128)  Mac=SHA1
EDH-RSA-DES-CBC3-SHA    SSLv3 Kx=DH       Au=RSA  Enc=3DES(168) Mac=SHA1
EDH-DSS-DES-CBC3-SHA    SSLv3 Kx=DH       Au=DSS  Enc=3DES(168) Mac=SHA1
DES-CBC3-SHA            SSLv3 Kx=RSA      Au=RSA  Enc=3DES(168) Mac=SHA1
DHE-RSA-SEED-SHA        SSLv3 Kx=DH       Au=RSA  Enc=SEED(128) Mac=SHA1
DHE-DSS-SEED-SHA        SSLv3 Kx=DH       Au=DSS  Enc=SEED(128) Mac=SHA1
SEED-SHA                SSLv3 Kx=RSA      Au=RSA  Enc=SEED(128) Mac=SHA1
RC4-SHA                 SSLv3 Kx=RSA      Au=RSA  Enc=RC4(128)  Mac=SHA1
RC4-MD5                 SSLv3 Kx=RSA      Au=RSA  Enc=RC4(128)  Mac=MD5 
EDH-RSA-DES-CBC-SHA     SSLv3 Kx=DH       Au=RSA  Enc=DES(56)   Mac=SHA1
EDH-DSS-DES-CBC-SHA     SSLv3 Kx=DH       Au=DSS  Enc=DES(56)   Mac=SHA1
DES-CBC-SHA             SSLv3 Kx=RSA      Au=RSA  Enc=DES(56)   Mac=SHA1
DES-CBC3-MD5            SSLv2 Kx=RSA      Au=RSA  Enc=3DES(168) Mac=MD5 
RC2-CBC-MD5             SSLv2 Kx=RSA      Au=RSA  Enc=RC2(128)  Mac=MD5 
RC4-MD5                 SSLv2 Kx=RSA      Au=RSA  Enc=RC4(128)  Mac=MD5 
DES-CBC-MD5             SSLv2 Kx=RSA      Au=RSA  Enc=DES(56)   Mac=MD5 
EXP-EDH-RSA-DES-CBC-SHA SSLv3 Kx=DH(512)  Au=RSA  Enc=DES(40)   Mac=SHA1 export
EXP-EDH-DSS-DES-CBC-SHA SSLv3 Kx=DH(512)  Au=DSS  Enc=DES(40)   Mac=SHA1 export
EXP-DES-CBC-SHA         SSLv3 Kx=RSA(512) Au=RSA  Enc=DES(40)   Mac=SHA1 export
EXP-RC2-CBC-MD5         SSLv3 Kx=RSA(512) Au=RSA  Enc=RC2(40)   Mac=MD5  export
EXP-RC4-MD5             SSLv3 Kx=RSA(512) Au=RSA  Enc=RC4(40)   Mac=MD5  export
EXP-RC2-CBC-MD5         SSLv2 Kx=RSA(512) Au=RSA  Enc=RC2(40)   Mac=MD5  export
EXP-RC4-MD5             SSLv2 Kx=RSA(512) Au=RSA  Enc=RC4(40)   Mac=MD5  export

28 cipher suites, that’s a lot! Let’s see if we can remove the unsafe ones first! You can see at the end of the of the list 7 ones marked as “export”. That means that they comply with the US cryptographic algorithm exportation policy. Those algorithms are utterly unsafe, and the US abandoned this restriction years ago, so let’s remove them:

Now, let’s remove the algorithms using plain DES (not 3DES) and RC2: ‘ALL:!ADH:!EXP:!LOW:!RC2:RC4+RSA:+HIGH:+MEDIUM’. That leaves us with 16 algorithms.

It is time to remove the slow algorithms! To decide, let’s use the openssl speed command. Use it on your server, ecause depending on your hardware, you might get different results. Here is the benchmark on my computer:

OpenSSL 0.9.8r 8 Feb 2011
built on: Jun 22 2012
options:bn(64,64) md2(int) rc4(ptr,char) des(idx,cisc,16,int) aes(partial) blowfish(ptr2) 
compiler: -arch x86_64 -fmessage-length=0 -pipe -Wno-trigraphs -fpascal-strings -fasm-blocks
  -DOPENSSL_PIC -DOPENSSL_THREADS -DZLIB -mmacosx-version-min=10.6
available timing options: TIMEB USE_TOD HZ=100 [sysconf value]
timing function used: getrusage
The 'numbers' are in 1000s of bytes per second processed.
type             16 bytes     64 bytes    256 bytes   1024 bytes   8192 bytes
md2               2385.73k     4960.60k     6784.54k     7479.39k     7709.04k
mdc2              8978.56k    10020.07k    10327.11k    10363.30k    10382.92k
md4              32786.07k   106466.60k   284815.49k   485957.41k   614100.76k
md5              26936.00k    84091.54k   210543.56k   337615.92k   411102.49k
hmac(md5)        30481.77k    90920.53k   220409.04k   343875.41k   412797.88k
sha1             26321.00k    78241.24k   183521.48k   274885.43k   322359.86k
rmd160           23556.35k    66067.36k   143513.89k   203517.79k   231921.09k
rc4             253076.74k   278841.16k   286491.29k   287414.31k   288675.67k
des cbc          48198.17k    49862.61k    50248.52k    50521.69k    50241.28k
des ede3         18895.61k    19383.95k    19472.94k    19470.03k    19414.27k
idea cbc             0.00         0.00         0.00         0.00         0.00 
seed cbc         45698.00k    46178.57k    46041.10k    47332.45k    50548.99k
rc2 cbc          22812.67k    24010.85k    24559.82k    21768.43k    23347.22k
rc5-32/12 cbc   116089.40k   138989.89k   134793.49k   136996.33k   133077.51k
blowfish cbc     65057.64k    68305.24k    72978.75k    70045.37k    71121.64k
cast cbc         48152.49k    51153.19k    51271.61k    51292.70k    47460.88k
aes-128 cbc      99379.58k   103025.53k   103889.18k   104316.39k    97687.94k
aes-192 cbc      82578.60k    85445.04k    85346.23k    84017.31k    87399.06k
aes-256 cbc      70284.17k    72738.06k    73792.20k    74727.31k    75279.22k
camellia-128 cbc        0.00         0.00         0.00         0.00         0.00 
camellia-192 cbc        0.00         0.00         0.00         0.00         0.00 
camellia-256 cbc        0.00         0.00         0.00         0.00         0.00 
sha256           17666.16k    42231.88k    76349.86k    96032.53k   103676.18k
sha512           13047.28k    51985.74k    91311.50k   135024.42k   158613.53k
aes-128 ige      93058.08k    98123.91k    96833.55k    99210.74k   100863.22k
aes-192 ige      76895.61k    84041.67k    78274.36k    79460.06k    77789.76k
aes-256 ige      68410.22k    71244.81k    69274.51k    67296.59k    68206.06k
                  sign    verify    sign/s verify/s
rsa  512 bits 0.000480s 0.000040s   2081.2  24877.7
rsa 1024 bits 0.002322s 0.000111s    430.6   9013.4
rsa 2048 bits 0.014092s 0.000372s     71.0   2686.6
rsa 4096 bits 0.089189s 0.001297s     11.2    771.2
                  sign    verify    sign/s verify/s
dsa  512 bits 0.000432s 0.000458s   2314.5   2181.2
dsa 1024 bits 0.001153s 0.001390s    867.6    719.4
dsa 2048 bits 0.003700s 0.004568s    270.3    218.9

We can remove the SEED and 3DES suite because they are slower than the other. DES was meant to be fast in hardware implementations, but slow in software, so 3DES (which runs DES three times) is slower. On the contrary, AES can be very fast in software implementations, and even more if your CPU provides specific instructions for AES. You can see that with a bigger key (and so, better theoretical security), AES gets slower. Depending on the level of security, you may choose different key sizes. According to the key length comparison, 128 might be enough for now. RC4 is a lot faster than other algorithms. AES is considered safer, but the implementation in SSL takes into account the attacks on RC4. So, we will propose this one in priority. Following recent researches, it appears that RC4 is not safe enough anymore. And ECDHE got a performance boost with recent versions of OpenSSL. So, let’s forbid RC4 right now!

So, here is the new cipher suite: ‘ALL:!ADH:!EXP:!LOW:!RC2:!3DES:!SEED:!RC4:+HIGH:+MEDIUM’

And the list of ciphers we will use:

DHE-RSA-AES256-SHA      SSLv3 Kx=DH       Au=RSA  Enc=AES(256)  Mac=SHA1
DHE-DSS-AES256-SHA      SSLv3 Kx=DH       Au=DSS  Enc=AES(256)  Mac=SHA1
AES256-SHA              SSLv3 Kx=RSA      Au=RSA  Enc=AES(256)  Mac=SHA1
DHE-RSA-AES128-SHA      SSLv3 Kx=DH       Au=RSA  Enc=AES(128)  Mac=SHA1
DHE-DSS-AES128-SHA      SSLv3 Kx=DH       Au=DSS  Enc=AES(128)  Mac=SHA1
AES128-SHA              SSLv3 Kx=RSA      Au=RSA  Enc=AES(128)  Mac=SHA1
RC4-SHA                 SSLv3 Kx=RSA      Au=RSA  Enc=RC4(128)  Mac=SHA1
RC4-MD5                 SSLv3 Kx=RSA      Au=RSA  Enc=RC4(128)  Mac=MD5 
RC4-MD5                 SSLv2 Kx=RSA      Au=RSA  Enc=RC4(128)  Mac=MD5

9 ciphers, that’s much more manageable. We could reduce the list further, but it is already in a good shape for security and speed. Configure it in Apache with this directive:

SSLHonorCipherOrder On

Configure it in Nginx with this directive:

ssl_ciphers ALL:!ADH:!EXP:!LOW:!RC2:!3DES:!SEED:!RC4:+HIGH:+MEDIUM

You can also see that the performance of RSA gets worse with key size. With the current security requirements (as of now, January 2013, if you are reading this from the future). You should choose a RSA key of 2048 bits for your certificate, because 1024 is not enough anymore, but 4096 is a bit overkill.

Remember, the benchmark depends on the version of OpenSSL, the compilation options and your CPU, so don’t forget to test on your server before implementing my recommandations.

Take care of the handshake

The SSL protocol is in fact two protocols (well, three, but the first is not interesting for us): the handshake protocol, where the client and the server will verify each other’s identity, and the record protocol where data is exchanged.

Here is a representation of the handshake protocol, taken from the TLS 1.0 RFC:

      Client                                               Server

      ClientHello                  -------->
                                   <--------      ServerHelloDone
      Finished                     -------->
                                   <--------             Finished
      Application Data             <------->     Application Data

You can see that there are 4 messages exchanged before any real data is sent. If a TCP packet takes 100ms to travel between the browser and your server, the handshake is eating 400ms before the server has sent any data!

And what happens if you make multiple connections to the same server? You do the handshake every time. So, you should activate Keep-Alive. The benefits are even bigger than for plain unencrypted HTTP.

Use this Apache directive to activate Keep-Alive:

KeepAlive On

Use this nginx directive to activate keep-alive:

keepalive_timeout 100

Present all the intermediate certification authorities in the handshake

During the handshake, the client will verify that the web server’s certificate is signed by a trusted certification authority. Most of the time, there is one or more intermediate certification authority between the web server and the trusted CA. If the browser doesn’t know the intermediate CA, it must look for it and download it. The download URL for the intermediate CA is usually stored in the “Authority information” extension of the certificate, so the browser will find it even if the web server doesn’t present the intermediate CA.

This means that if the server doesn’t present the intermediate CA certificates, the browser will block the handshake until it has downloaded them and verified that they are valid.

So, if you have intermediate CAs for your server’s certificate, configure your webserver to present the full certification chain. With Apache, you just need to concatenate the CA certificates, and indicate them in the configuration with this directive:

SSLCertificateChainFile /path/to/certification/chain.pem

For nginx, concatenate the CA certificate to the web server certificate and use this directive:

ssl_certificate /path/to/certification/chain.pem

Activate caching for static assets

By default, the browsers will not cache content served over SSL, for security. That means that your static assets (Javascript, CSS, pictures) will be reloaded on every call. Here is a big performance failure!

The fix for that: set the HTTP header “Cache-Control: public” for the static assets. That way, the browser will cache them. But don’t activate it for the sensitive content, beacuase it should not be cached on the disk by your browser.

You can use this directive to enable Cache-Control:

<filesMatch ".(js|css|png|jpeg|jpg|gif|ico|swf|flv|pdf|zip)$">
Header set Cache-Control "max-age=31536000, public"

The files will be cached for a year with the max-age option.

For nginx, use this:

location ~ \.(js|css|png|jpeg|jpg|gif|ico|swf|flv|pdf|zip)$ {
    expires 24h;
    add_header Cache-Control public;

Update: it looks like Firefox ignores the Cache-Control and caches everything from SSL connections, unless you use the “no-store” option.

Beware of CDN with multiple domains

If you followed a bit the usual performance tips, you already offloaded your static assets (Javascript, CSS, pictures) to a content delivery network. That is a good idea for a SSL deployment too, BUT, there are caveats:

  • your CDN must have servers accessible over SSL, otherwise you will see the “mixed content” warning
  • it must have “Keep-Alive” and “Cache-control: public” activated
  • it should serve all your assets from only one domain!

Why the last one? Well, even if multiple domains point to the same IP, the browser will do a new handshake for every domain. So, here, we must go against the common wisdom of separating your assets on multiple domains to profit from the parallelized request in the browser. If all the assets are served from the same domain, there will only be one handshake. It could be fixed to allow multiple domains, but this is beyond the scope of this article.


I could talk for hours about how you could tweak your web server performance with SSL. There is alot more to it than these easy tips, but I hope those will be of useful for you!

If you want to know more, I am currently writing an ebook about SSL tuning, and I would love to hear your comments about it!

If you need help with your SSL configuration, I am available for consulting, and always happy to work on interesting architectures.

By the way, if you want to have a good laugh with SSL, read “How to get a certificate signed by multiple certification authorities” 🙂

PilotSSH: manage your server in a few touches

I just released Pilot SSH, a server administration application for iPhone. So, why another SSH application? Aren’t there dozens of these already?

I tried a lot of those shell applications, and they felt clunky on a phone. They are fine with a tablet (even more if you use a bluetooth keyboard), but writing commands on a phone’s keyboard is not really intuitive. Moreover, the small screen of a phone is not really usable to display the command results.

But I reaaaaally wanted to manage my servers from my phone. Because I am not always in front of my computer. Because I am too lazy to get the laptop from the bag, open it, plug the 3G key or find WiFi, connect over SSH and type a command to restart a crashed web server. Because it would be awesome to be in a bar and say “hold on, I have update my server”, open my phone and do it in 3 touches.

So, here it is, Pilot SSH, in all its glory, can out of the box:

  • display running processes, the memory they use, and kill them
  • show which websites are enabled or disabled in Apache
  • display the uptime, halt or reboot the server
  • show Apache logs
Pilot SSH process list

Pilot SSH process list

But there is more! The application is completely extensible, because it uses scripts stored on the server side, in your home, in ~/.pilotssh. You can totally replace the current scripts, download more from the Github repository, and make your own! The scripts can be written in any language, as long as they return a JSON string conforming to the API.

I already got a contribution soon after the launch, with a script to flush the caches. And I have a lot of ideas for new scripts:

  • upgrade a WordPress website
  • display the status of processes managed by Monit
  • create/remove users
  • Support nginx too
  • Display more logs

This is just the beginning, and I expect a lot of impressive ideas from the users of Pilot SSH. I can’t wait to see them!

Do you want to try Pilot SSH? Everything you need is on its website!