Category: Apple

Can Apple read your iMessages?

About a year ago I wrote a short post urging Apple to publish the technical details of iMessage encryption. I’d love tell you that Apple saw my influential crypto blogging and fell all over themselves to produce a spec, but, no. iMessage is the same black box it’s always been.

What’s changed is that suddenly people seem to care. Some of this interest is due to Apple’s (alleged) friendly relationship with the NSA. Some comes from their not-so-friendly relationship with the DEA. Whatever the reason, people want to know which of our data Apple has and who they’re sharing it with.

And that brings us back to iMessage encryption. Apple runs one of the most popular encrypted communications services on Earth, moving over two billion iMessage every day. Each one is loaded with personal information the NSA/DEA would just love to get their hands on. And yet Apple claims they can’t. In fact, even Apple can’t read them:

There are certain categories of information which we do not provide to law enforcement or any other group because we choose not to retain it.

For example, conversations which take place over iMessage and FaceTime are protected by end-to-end encryption so no one but the sender and receiver can see or read them. Apple cannot decrypt that data.

This seems almost too good to be true, which in my experience means it probably is. My view is inspired by something I like to call “Green’s law of applied cryptography”, which holds that applied cryptography mostly sucks. Crypto never offers the unconditional guarantees you want it to, and when it does your users suffer terribly.

And that’s the problem with iMessage: users don’t suffer enough. The service is almost magically easy to use, which means Apple has made tradeoffs — or more accurately, they’ve chosen a particular balance between usability and security. And while there’s nothing wrong with tradeoffs, the particulars of their choices make a big difference when it comes to your privacy. By witholding these details, Apple is preventing its users from taking steps to protect themselves.

The details of this tradeoff are what I’m going to talk about in this post. A post which I swear will be the last post I ever write on iMessage. From here on out it’ll be ciphers and zero knowledge proofs all the way.

Apple backs up iMessages to iCloud

That’s the super-secret
NSA spying chip.
The biggest problem with Apple’s position is that it just plain isn’t true. If you use the iCloud backup service to back up your iDevice, there’s a very good chance that Apple can access the last few days of your iMessage history.
For those who aren’t in the Apple ecosystem: iCloud is an optional backup service that Apple provides for free. Backups are great, but if iMessages are backed up we need to ask how they’re protected. Taking Apple at their word — that they really can’t get your iMessages — leaves us with two possibilities:
  1. iMessage backups are encrypted under a key that ‘never leaves the device‘.
  2. iMessage backups are encrypted using your password as a key.

Unfortunately neither of these choices really works — and it’s easy to prove it. All you need to do is run the following simple experiment: First, lose your iPhone. Now change your password using Apple’s iForgot service (this requires you to answer some simple security questions or provide a recovery email). Now go to an Apple store and shell out a fortune buying a new phone.

If you can recover your recent iMessages onto a new iPhone — as I was able to do in an Apple store this afternoon — then Apple isn’t protecting your iMessages with your password or with a device key. Too bad. (Update 6/27: Ashkan Soltani also has some much nicer screenshots from a similar test.)

The sad thing is there’s really no crypto to understand here. The simple and obvious point is this: if I could do this experiment, then someone at Apple could have done it too. Possibly at the request of law enforcement. All they need are your iForgot security questions, something that Apple almost certainly does keep.* 

Apple distributes iMessage encryption keys

But maybe you don’t use backups. In this case the above won’t apply to you, and Apple clearly says that their messages are end-to-end encrypted. The question you should be asking now is: encrypted to whom?

The problem here is that encryption only works if I have your encryption key. And that means before I can talk to you I need to get hold of it. Apple has a simple solution to this: they operate a directory lookup service that iMessage can use to look up the public key associated with any email address or phone number. This is great, but represents yet another tradeoff: you’re now fundamentally dependent on Apple giving you the right key.

HTTPS request/response containing a
“message identity key” associated with an
iPhone phone number (modified). These keys are
sent over SSL.

The concern here is that Apple – or a hacker who compromises Apple’s directory server – might instead deliver their own key. Since you won’t know the difference, you’ll be encrypting to that person rather than to your friend.**

Moreover, iMessage lets you associate multiple public keys with the same account — for example, you can you add a device (such as a Mac) to receive copies of messages sent to your phone. From what I can tell, the iMessage app gives the sender no indication of how many keys have been associated with a given iMessage recipient, nor does it warn them if the recipient suddenly develops new keys.

The practical upshot is that the integrity of iMessage depends on Apple honestly handing out keys. If they cease to be honest (or if somebody compromises the iMessage servers) it may be possible to run a man-in-the-middle attack and silently intercept iMessage data.

Now to some people this is obvious, and to other’s it’s no big deal. All of which is fine. But people should at least understand the strengths and weaknesses of the particular design that Apple has chosen. Armed with that knowledge they can make up their minds how much they want to trust Apple.

Apple can retain metadata

While Apple may encrypt the contents of your communication, their statement doesn’t exactly rule out the possibility they store who you’re talking to. This is the famous meta-data the NSA already sweeps up and (as I’ve said before) it’s almost impossible not to at least collect this information, especially since Apple actually delivers your messages through their servers.

This metadata can be as valuable as the data itself. And while Apple doesn’t retain the content of your messages, their statement says nothing about all that metadata.

Apple doesn’t use Certificate Pinning

As a last – and fairly minor point – iMessage client applications (for iPhone and Mac) communicate with Apple’s directory service using the HTTPS protocol. (Note that this applies to directory lookup messages: the actual iMessages are encrypted separately and travel over XMPP Apple’s push network protocol.)

Using HTTPS is a good thing, and in general it provides strong protections against interception. But it doesn’t protect against all attacks. There’s still a very real possibility that a capable attacker could obtain a forged certificate (possibly by compromising a Certificate Authority) and thus intercept or modify communications with Apple.

This kind of thing isn’t as crazy as it sounds. It happened to hundreds of thousands of Iranian Gmail users, and it’s likely to happen again in the future. The standard solution to this problem is called ‘certificate pinning‘ — this essentially tells the application not to trust unknown certificates. Many apps such as Twitter do this. However based on the testing I did while writing this post, Apple doesn’t.

Conclusion

I don’t write any of this stuff because I dislike Apple. In fact I love their products and would bathe with them if it didn’t (unfortunately) violate the warranty.

But the flipside of my admiration is simple: I rely on these devices and want to know how secure they are. I see absolutely no downside to Apple presenting at least a high-level explanation to experts, even if they keep the low-level details to themselves. This would include the type and nature of the encryption algorithms used, the details of the directory service and the key agreement protocol.

Apple may Think Different, but security rules apply to them too. Sooner or later someone will compromise or just plain reverse-engineer the iMessage system. And then it’ll all come out anyway.

Notes:

* Of course it’s possible that Apple is using your security questions to derive an encryption key. However this seems unlikely. First because it’s likely that Apple has your question/answers on file. But even if they don’t, it’s unlikely that many security answers contain enough entropy to use for encryption. There are only so many makes/models of cars and so many birthdays. Apple’s 2-step authentication may improve things if you use it — but if so Apple isn’t saying.

** In practice it’s not clear if Apple devices encrypt to this key directly or if they engage in an OTR-like key exchange protocol. What is clear is that iMessage does not include a ‘key fingerprint’ or any means for users to verify key authenticity, which means fundamentally you have to trust Apple to guarantee the authenticity of your keys. Moreover iMessage allows you to send messages to offline users. It’s not clear how this would work with OTR.

Dear Apple: Please set iMessage free

Normally I avoid complaining about Apple because (a) there are plenty of other people carrying that flag, and (b) I honestly like Apple and own numerous lovely iProducts. I’m even using one to write this post.

Moroever, from a security point of view, there isn’t that much to complain about. Sure, Apple has a few irritating habits — shipping old, broken versions of libraries in its software, for example. But on the continuum of security crimes this stuff is at best a misdemeanor, maybe a half-step above ‘improper baby naming‘. Everyone’s software sucks, news at 11.

There is, however, one thing that drives me absolutely nuts about Apple’s security posture. You see, starting about a year ago Apple began operating one of the most widely deployed encrypted text message services in the history of mankind. So far so good. The problem is that they still won’t properly explain how it works.

And nobody seems to care.

I am, of course, referring to iMessage, which was deployed last year in iOS Version 5. It allows — nay, encourages — users to avoid normal carrier SMS text messages and to route their texts through Apple instead.

Now, this is not a particularly new idea. But iMessage is special for two reasons. First it’s built into the normal iPhone texting application and turned on by default. When my Mom texts another Apple user, iMessage will automatically route her message over the Internet. She doesn’t have to approve this, and honestly, probably won’t even know the difference.

Secondly, iMessage claims to bring ‘secure end-to-end encryption‘ (and authentication) to text messaging. In principle this is huge! True end-to-end encryption should protect you from eavesdropping even by Apple, who carries your message. Authentication should protect you from spoofing attacks. This stands in contrast to normal SMS which is often not encrypted at all.

So why am I looking a gift horse in the mouth? iMessage will clearly save you a ton in texting charges and it will secure your messages for free. Some encryption is better than none, right?

Well maybe.

To me, the disconcerting thing about iMessage is how rapidly it’s gone from no deployment to securing billions of text messages for millions of users. And this despite the fact that the full protocol has never been published by Apple or (to my knowledge) vetted by security experts. (Note: if I’m wrong about this, let me know and I’ll eat my words.)

What’s worse is that Apple has been hyping iMessage as a secure protocol; they even propose it as a solution to some serious SMS spoofing bugs. For example:

Apple takes security very seriously. When using iMessage instead of SMS, addresses are verified which protects against these kinds of spoofing attacks. One of the limitations of SMS is that it allows messages to be sent with spoofed addresses to any phone, so we urge customers to be extremely careful if they’re directed to an unknown website or address over SMS.

And this makes me nervous. While iMessage may very well be as secure as Apple makes it out to be, there are plenty of reasons to give the protocol a second look.

For one thing, it’s surprisingly complicated.

iMessage is not just two phones talking to each other with TLS. If this partial reverse-engineering of the protocol (based on the MacOS Mountain Lion Messages client) is for real, then there are lots of moving parts. TLS. Client certificates. Certificate signing requests. New certificates delivered via XML. Oh my.

As a general rule, lots of moving parts means lots of places for things to go wrong. Things that could seriously reduce the security of the protocol. And as far as I know, nobody’s given this much of  a look. It’s surprising.

Moreover, there are some very real questions about what powers Apple has when it comes to iMessage. In principle ‘end-to-end’ encryption should mean that only the end devices can read the connection. In practice this is almost certainly not the case with iMessage. A quick glance at the protocol linked above is enough to tell me that Apple operates as a Certificate Authority for iMessage devices. And as a Certificate Authority, it may be able to substantially undercut the security of the protocol. When would Apple do this? How would it do this? Are we allowed to know?

Finally, there have been several reports of iMessages going astray and even being delivered to the wrong (or stolen) devices. This stuff may all have a reasonable explanation, but it’s yet another set of reasons why we it would be nice to understand iMessage better than we do now if we’re going to go around relying on it.

So what’s my point with all of this?

This is obviously not a technical post. I’m not here to present answers, which is disappointing. If I knew the protocol maybe I’d have some. Maybe I’d even be saying good things about it.

Rather, consider this post as a plea for help. iMessage is important. People use it. We ought to know how secure it is and what risks those people are taking by using it. The best solution would be for Apple to simply release a detailed specification for the protocol — even if they need to hold back a few key details. But if that’s not possible, maybe we in the community should be doing more to find out.

Remember, it’s not just our security at stake. People we know are using these products. It would be awfully nice to know what that means.

iCloud: Who holds the key?

Ars Technica brings us today’s shocking privacy news: ‘Apple holds the master decryption key when it comes to iCloud security, privacy‘. Oh my.

The story is definitely worth a read, though it may leave you shaking your head a bit. Ars’s quoted security experts make some good points, but they do it in a strange way — and they propose some awfully questionable fixes.

But maybe I’m too picky. To be honest, I didn’t realize that there was even a question about who controlled the encryption key to iCloud storage. Of course Apple does — for obvious technical reasons that I’ll explain below. You don’t need to parse Apple’s Terms of Service to figure this out, which is the odd path that Ars’s experts have chosen:

In particular, Zdziarski cited particular clauses of iCloud Terms and Conditions that state that Apple can “pre-screen, move, refuse, modify and/or remove Content at any time” if the content is deemed “objectionable” or otherwise in violation of the terms of service. Furthermore, Apple can “access, use, preserve and/or disclose your Account information and Content to law enforcement authorities” whenever required or permitted by law.

Well, fine, but so what — Apple’s lawyers would put stuff like this into their ToS even if they couldn’t access your encrypted content. This is what lawyers do. These phrases don’t prove that Apple can access your encrypted files (although, I remind you, they absolutely can), any more than Apple’s patent application for a 3D LIDAR camera ‘proves’ that you’re going to get one in your iPhone 5.

Without quite realizing what I was doing, I managed to get myself into a long Twitter-argument about all this with the Founder & Editor-in-Chief of Ars, a gentleman named Ken Fisher. I really didn’t mean to criticize the article that much, since it basically arrives at the right conclusions — albeit with a lot of nonsense along the way.

Since there seems to be some interest in this, I suppose it’s worth a few words. This may very well be the least ‘technical’ post I’ve ever written on this blog, so apologies if I’m saying stuff that seems a little obvious. Let’s do it anyway.

The mud puddle test

You don’t have to dig through Apple’s ToS to determine how they store their encryption keys. There’s a much simpler approach that I call the ‘mud puddle test’:

  1. First, drop your device(s) in a mud puddle.
  2. Next, slip in said puddle and crack yourself on the head. When you regain consciousness you’ll be perfectly fine, but won’t for the life of you be able to recall your device passwords or keys.
  3. Now try to get your cloud data back.

Did you succeed? If so, you’re screwed. Or to be a bit less dramatic, I should say: your cloud provider has access to your ‘encrypted’ data, as does the government if they want it, as does any rogue employee who knows their way around your provider’s internal policy checks.

And it goes without saying: so does every random attacker who can guess your recovery information or compromise your provider’s servers.

Now I realize that the mud puddle test doesn’t sound simple, and of course I don’t recommend that anyone literally do this — head injuries are no fun at all. It’s just a thought experiment, or in the extreme case, something you can ‘simulate’ if you’re willing to tell your provider few white lies.

But you don’t need to simulate it in Apple’s case, because it turns out that iCloud is explicitly designed to survive the mud puddle test. We know this thanks to two iCloud features. These are (1) the ability to ‘restore’ your iCloud backups to a brand new device, using only your iCloud password, and (2) the ‘iForgot’ service, which lets you recover your iCloud password by answering a few personal questions.

Since you can lose your device, the key isn’t hiding there. And since you can forget your password, it isn’t based on that. Ergo, your iCloud data is not encrypted end-to-end, not even using your password as a key (or if it is, then Apple has your password on file, and can recover it from your security questions.) (Update: see Jonathan Zdziarski’s comments at the end of this post.)

You wanna make something of it?

No! It’s perfectly reasonable for a consumer cloud storage provider to design a system that emphasizes recoverability over security. Apple’s customers are far more likely to lose their password/iPhone than they are to be the subject of a National Security Letter or data breach (hopefully, anyway).

Moreover, I doubt your median iPhone user even realizes what they have in the cloud. The iOS ‘Backup’ service doesn’t advertise what it ships to Apple (though there’s every reason to believe that backed up data includes stuff like email, passwords, personal notes, and those naked photos you took.) But if people don’t think about what they have to lose, they don’t ask to secure it. And if they don’t ask, they’re not going to receive.

My only issue is that we have to have this discussion in the first place. That is, I wish that companies like Apple could just come right out and warn their users: ‘We have access to all your data, we do bulk-encrypt it, but it’s still available to us and to law enforcement whenever necessary’. Instead we have to reverse-engineer it by inference, or by parsing through Apple’s ToS. That shouldn’t be necessary.

But can’t we fix this with Public-Key Encryption/Quantum Cryptography/ESP/Magical Unicorns?

No, you really can’t. And this is where the Ars Technica experts go a little off the rails. Their proposed solution is to use public-key encryption to make things better. Now this is actually a great solution, and I have no objections to it. It just won’t make things better.

To be fair, let’s hear it in their own words:

First, cloud services should use asymmetric public key encryption. “With asymmetric encryption, the privacy and identity of each individual user” is better protected, Gulri said, because it uses one “public” key to encrypt data before being sent to the server, and uses another, “private” key to decrypt data pulled from the server. Assuming no one but the end user has access to that private key, then no one but the user—not Apple, not Google, not the government, and not hackers—could decrypt and see the data.

I’ve added the boldface because it’s kind of an important assumption.

To make a long story short, there are two types of encryption scheme. Symmetric encryption algorithms have a single secret key that is used for both encryption and decryption. The key can be generated randomly, or it can be derived from a password. What matters is that if you’re sending data to someone else, then both you and the receiver need to share the same key.

Asymmetric, or public-key encryption has two keys, one ‘public key’ for encryption, and one secret key for decryption. This makes it much easier to send encrypted data to another person, since you only need their public key, and that isn’t sensitive at all.

But here’s the thing: the difference between these approaches is only related to how you encrypt the data. If you plan to decrypt the data — that is, if you ever plan to use it — you still need a secret key. And that secret key is secret, even if you’re using a public-key encryption scheme.

Which brings us to the real problem with all encrypted storage schemes: someone needs to hold the secret decryption key. Apple has made the decision that consumers are not in the best position to do this. If they were willing to allow consumers to hold their decryption keys, it wouldn’t really matter whether they were using symmetric or public-key encryption.

So what is the alternative?

Well, for a consumer-focused system, maybe there really isn’t one. Ultimately people back up their data because they’re afraid of losing their devices, which cuts against the idea of storing encryption keys inside of devices.

You could take the PGP approach and back up your decryption keys to some other location (your PC, for example, or a USB stick). But this hasn’t proven extremely popular with the general public, because it’s awkward — and sometimes insecure.

Alternatively, you could use a password to derive the encryption/decryption keys. This approach works fine if your users pick decent passwords (although they mostly won’t), and if they promise not to forget them. But of course, the convenience of Apple’s “iForgot” service indicates that Apple isn’t banking on users remembering their passwords. So that’s probably out too.

In the long run, the answer for non-technical users is probably just to hope that Apple takes good care of your data, and to hope you’re never implicated in a crime. Otherwise you’re mostly out of luck. For tech-savvy users, don’t use iCloud and do try to find a better service that’s willing to take its chances on you as the manager of your own keys.

In summary

I haven’t said anything in this post that you couldn’t find in Chapter 1 of an ‘Intro to Computer Security’ textbook, or a high-level article on Wikipedia. But these are important issues, and there seems to be confusion about them.

The problem is that the general tech-using public seems to think that cryptography is a magical elixir that can fix all problems. Companies — sometimes quite innocently — market ‘encryption’ to convince people that they’re secure, when in fact they’re really not. Sooner or later people will figure this out and things will change, or they won’t and things won’t. Either way it’ll be an interesting ride.

Update 4/4: Jonathan Zdziarski ‏tweets to say my ‘mud puddle’ theory is busted: since the iForgot service requires you to provide your birthdate and answer a ‘security question’, he points out that this data could be used as an alternative password, which could encrypt your iCloud password/keys — protecting them even from Apple itself.

The problem with his theory is that security answers don’t really make very good keys, since (for most users) they’re not that unpredictable. Apple could brute-force their way through every likely “hometown” or “favorite sport” in a few seconds. Zdziarski suggests that Apple might employ a deliberately slow key derivation function to make these attacks less feasible, and I suppose I agree with him in theory. But only in theory. Neither Zdziarski or I actually believe that Apple does any of this.