On the Mac App Store

I’ve just come off iDeveloper.TV Live with Scotty and John, where we were talking about the Mac app store. I had some material prepared about the security side of the app store that we didn’t get on to – here’s a quick write up.

There’s a lot of discussion on twitter and the macsb mailing list, and doubtless elsewhere, about the encryption paperwork that Apple are making us fill in. It’s not Apple’s fault, it’s the U.S. Department of Commerce. You see, back in the cold war (and, frankly, ever since) the government have been of the opinion that encryption is a weapon (because it hides data from their agents) and so are powerful computers (because they can do encryption that’s expensive to crack). So the Bureau of Industry and Security developed the Export Administration Regulations to control the flow of such heinous weapons through the commercial sector.

Section 5, part 2 covers computer equipment and software. Specific provision is made for encryption, in the documentation we find that Items may be controlled as encryption items even if the encryption is actually performed by the operating system, an external library, a third-party product or a cryptographic processor. If an item uses encryption functionality, whether or not the code that performs the encryption is included with the item, then BIS evaluates the item based on the encryption functionality it uses.

So there you go. If you’re exporting software from the U.S. (and you are, if you’re selling via Apple’s app store) then you need to fill in the export notification.

Other Mac App Store security things, in “oh God is it that late already” format:

  • Receipt validation. No different really from existing licensing frameworks. All you can do is make it hard to find the tests from the binary. I had an idea about a specific way to do that, but want to test it before I release it. As you’ve no doubt found, anti-cracking measures aren’t easy.
  • Users. The user base for the MAS will be wider, and less tech-savvy, than the users existing micro-ISVs are selling to. Make sure your intent with regard to user data, particularly the consequences of your app’s workflow, are clear.
  • Similarly, be clear about the content of updates. Clearer than Apple are: “contains various fixes and improvements” WTF?
  • As we’ve found with the iOS store, it’s harder to push an update out than when you host the download yourself. Getting security right (or, pragmatically, not too wrong) the first time avoids emergency update submissions.
  • Permissions. Your app needs to run entirely as the current user, who may not be an admin. If you’re a developer, you’re probably running as an admin. Test with a non-admin account. Better, do all of your development in a non-admin account. Add yourself to the _developer group so you can still use gdb/Instruments properly.

Did the UK create a new kind of “Crypto Mule”?

It’s almost always the case that a new or changed law means that there is a new kind of criminal, because there is by definition a way to contravene the new law. However, when the law allows the real criminals to hide behind others who will take the fall, that’s probably a failure in the legislation.

The Regulation of Investigatory Powers Act 2000 may be doing just that. In Section 51, we find that a RIPA order to disclose information can be satisfied by disclosing the encryption key, if the investigating power already has the ciphertext.

Now consider this workflow. Alice Qaeda needs to send information confidentially to Bob Laden (wait: Alice and Bob aren’t always the good guys? Who knew?). She doesn’t want it intercepted by Eve Sergeant, who works for SOCA (wait: Eve isn’t always the bad guy etc.). So she prepares the information, and encrypts it using Molly Mule’s public key. She then gives the ciphertext to Michael Mule.

Michael’s job is to get from Alice’s location to Bob’s. Molly is also at Bob’s location, and can use her private key to show the plaintext to Bob. She doesn’t necessarily see the plaintext herself; she just prepares it for Bob to view.

Now Alice and Bob are notoriously difficult for Eve to track down, so she stops Michael and gets her superintendent to write a RIPA demand for the encryption key. But Michael doesn’t have they key. He’ll still probably get sent down for two years on a charge of failing to comply with the RIPA request. Even if Eve manages to locate and serve Molly with the same request, Molly just needs to lie about knowing the key and go down for two years herself.

The likelihood is that Molly and Michael will be coerced into performing their roles, just as mules are in other areas of organised crime. So has the legislation, in trying to set out government snooping permissions, created a new slave trade in crypto mules?

On how to get crypto wrong

I’ve said time and time again: don’t write your own encryption algorithm. Once you’ve chosen an existing algorithm, don’t write your own implementation.

Today I had to look at an encryption library that had been developed to store some files in an app. The library used a custom implementation of SHA256-HMAC, and a custom implementation of CBC mode. The implementations certainly looked OK, and seemed to match the descriptions in the textbooks. They also seem to work – you can encrypt a file to get gibberish, and decrypt the gibberish to get the file back.

So the first thing I did was to crack open Xcode and replace these custom functions with CommonCrypto. CommonCrypto’s internals also look a lot like the textbook descriptions of the methods, too. So it would be surprising if these two approaches yielded different results.

These two approaches yielded different results. This was surprising. Specifically, I found that the CBC implementation would sometimes use junk memory, which the CommonCrypto version never does. Of course, the way in which this junk was used was predictable enough that the encryption routine was still reversible – but could it be that the custom implementation was leaking information about the plaintext in the cipher-text by inappropriate re-use of the buffer? Possibly, and that’s good enough for me to throw the custom implementation out. Proving whether or not this implementation is “safe” is something that a specialist cryptographer could probably do in half a day. However, as I was able to use half a day to produce something I had more confidence in, just by using a tested implementation, I decided there was no need to do that work.

A site for discussing app security

There’s a new IT security site over at Stack Exchange. Questions and answers on designing and implementing IT security policy, and on app security are all welcome.

I’m currently a moderator at the site, but that’s just an interim thing while the site is being bootstrapped. Obviously, if people subsequently vote for me as a permanent moderator I’ll stay in, but the converse is also true. Anyway, check out the site, ask and answer questions, let’s make it as good a venue for app security discussion as stackoverflow.com is for general programming.

On Fuzzy Aliens

I have just launched a new company, Fuzzy Aliens[*], offering application security consultancy services for smartphone app developers. This is not the FAQ list, this is the “questions I want to answer so that they don’t become frequently asked” list.

What do you offer?

The company’s services are all focussed on helping smartphone and tablet app developers discover and implement their applications’ security and privacy requirements. When planning an app, I can help with threat modelling, with training developers, securing the development lifecycle, requirements elicitation, secure user experience design, and with developing a testing strategy.

When it comes to implementation, you can hire me to do the security work on your iOS or Android app. That may be some background “plumbing” like storing a password or encrypting sensitive content, or it might be an end-to-end security feature. I can also do security code reviews and vulnerability analysis on existing applications.

Why would I want that?

If you’re developing an application destined for the enterprise market, you probably need it. Company I.T. departments will demand applications that conform to local policy regarding data protection, perhaps based on published standards such as the ISO 27000 family or PCI-DSS.

In the consumer market, users are getting wise to the privacy problems associated with mobile apps. Whether it’s accidentally posting the wrong thing to facebook, or being spied on by their apps, the public don’t want to—and shouldn’t need to—deal with security issues when they’re trying to get their work done and play their games.

Can I afford that?

Having been a Micro-ISV and contracted for others, I know that many apps are delivered under tight budgets by one-person companies. If all you need is a half day together to work on a niggling problem, that’s all you need to pay for. On the other hand I’m perfectly happy to work on longer projects, too :).

Why’s it called Fuzzy Aliens?

Well, the word “fuzz” obviously has a specific meaning in the world of secure software development, but basically the answer is that I knew I could turn that into a cute logo (still pending), and that it hadn’t been registered by a UK Ltd yet.

So how do I contact you about this?

You already have – you’re here. But you could see the company’s contact page for more specific information.


[*] More accurately, I have indicated the intent to do so. The articles of association have not yet been returned by Companies House, so for the next couple of days the blue touch paper is quietly smouldering.

On secrets

Secrets are hard. Especially in the digital domain, but we can see examples in other environments too. Let’s take a look at a couple of historical examples.

It used to be the case that all of Britain’s diplomatic traffic was safe from snooping. Why? The information was all conveyed over the telegraph system, and Britain controlled the telegraph system. Customer states could buy access to send and receive their own signals over the network. This of course meant that Britain could snoop on their signals. Where the cables went through neutral (or supposedly neutral) countries, said countries and their allies (who were not necessarily Britain’s allies) could also snoop on the traffic. Wait, didn’t I say this was a safe channel?

Even were the telegraph system snoop-proof, the telegraph operators might not be. The recipients of any message might not be. Come to that, neither might the senders. Because the British foreign office knew the communications to be secret, everyone else knew that this was where to look for their secrets.

Conversely, it has never been assumed that knowing how to make a nuclear weapon is an unknown secret. It’s trivial for anyone to get the plans to a nuke, and if you need parts, just look at the United States export restrictions documents and order those parts from Germany. So how come no-one has been nuked in 65 years? How come Al Qaeda aren’t busy nuking the western world, if they know how to do it? Because while nuking is easy to know, it’s hard to do. Acquiring the fuel is hard enough for most states, never mind small terrorist cells. And then getting the fuel into a bomb and the bomb into a target without incident is so hard that it’s not worth doing.

Conclusion? Often, making things secret isn’t sufficient. Secrecy is fleeting. Making it hard to use a preferably-secret fact can be more effective than ramping up the secrecy.

On utilities

When I worked on an antivirus application, we used to have a joke in our team that we’d choose which one of us would accept the Apple Design Award for our product. Not that we weren’t striving for ADA-quality work; we just knew that Apple would never suffer an anti-virus app to gain that sort of recognition. It’s not what they want customers to associate with the platform.

This doesn’t just apply to AV: any utility app falls into the same situation. The reason is that utilities exist to make up for shortcomings in the computing experience.

No-one wants to use a utility. You don’t wake up full of joy at the prospect of defragmenting your hard drive; you wake up hoping to write a great novel. Or put together that movie from your holiday. Or write a killer iPhone app. You defragmenting your hard drive because it needs doing; because the computer didn’t take care of it for you automatically. Writing your novel needs to wait while you twiddle with the internal workings of something called a filesystem.

Similarly, no-one wants to use anti-virus. It’s just that no-one wants to use a virus either. The computer lets you down by making it possible to run viruses, just like it lets you down by having a fragmented filesystem. And you have to suffer this let-down by running a utility app.

Any utility app – even a very well-written one – is symptomatic of a let-down in the computing experience. That’s why you don’t find utilities on the iPhone app store – and the conditions of the Mac app store will limit the availability of utilities there, too. Apple have no interest in making it easy for users to find the let-downs in the computing experience. (Readers with long memories will remember that even some of the built-in utilities on OS X were, for a long time, part of an optional package.)

Hitherto, most security features have been utilities – because the platform security has been a let-down. Anti-virus: let-down. Mail filters: let-down. Encryption: let-down. The way to get your application noticed is not to make a utility to address the let-down: it’s to design the let-down out of your application. Create something that lets users do what they want; without the compromises that lead to needing utilities. In other words, design the security into the application experience.

On phone support scams and fake AV

A couple of weeks ago, I posted on Twitter about a new scam:

Heard about someone who was phoned by a man “from Windows” who engineered his way into remote access to the mark’s computer.

Fast forward to now, the same story has finally been picked up by the security vendors and the mainstream media. This means it’s probably time to go into more depth.

I heard a first-hand account of the scam. The victim is the kind of person who shouldn’t be expected to understand IT security – a long distance lorry driver who uses his computer for browsing, e-mail, and that sort of thing. As he tells it, the person called, saying they were from Windows and that they had discovered his computer was infected. He was given instructions to give the caller remote access to help clean up the computer.

With remote access, the caller was able to describe some of the problems the victim was having with his computer, while taking control to “fix them”. The caller eventually discovered that the victim’s anti-virus was out of date, and that if he gave the caller his payment information he could get new software for £109. This is when the victim hung up; however his computer has not booted properly since then.

I think my audience here is probably tech-savvy enough not to need warning about scams like this, and to understand that the real damage was done even before any discussion of payments was made (hint: browser form-auto-fill data). It’s not the scam itself I want to focus on, but our reaction.

Some people I have told this story to in real life (it does happen) have rolled their eyes, and said something along the lines of “well of course the users are the weakest link” in a knowing way. If that’s true, why rely on the users to make all the security decisions? Why leave it to them to decide what’s legitimate and what’s scammy, as was the case here? Why is the solution to any problem to shovel another bucketload of computer knowledge on them and hope that it sticks, as Sophos and the BBC have tried in the articles above?

No. This is not a solution to anything. No matter how loudly you shout about how that isn’t how Microsoft does business, someone who says he is from Microsoft will phone your users up and tell them that it is.

This is the same problem facing anti-virus vendors trying to convince us not to get fooled by FakeAV scams. Vendor A tells us to buy their product instead of Vendor B’s, because it’s better. So, is Vendor A the FakeAV pedlar, or B? Or is it both? Or neither? You can’t tell.

It may seem that this is a problem that cannot be solved in technology, that it relies on hard-wired behaviour of us bald apes. I don’t think that’s so. I think that it would be possible to change the way we, legitimate software vendors, interact with our users, and the way they interact with our software, such that an offline scam like this would never come to pass. A full discussion would fill a whole whitepaper that I haven’t written yet. However, to take the most extreme point from it, the one I know you’re going to loathe, what if our home computers were managed remotely by the vendors? Do most users really need complete BIOS and kernel level access to their kit? Really?

Look for the whitepaper sometime in the new year.

On free Mac Anti-Virus

On Tuesday, my pals at my old stomping ground Sophos launched their Free home edition Mac product. I’ve been asked by several people what makes it tick, so here’s Mac Anti-Virus In A Nutshell.

Sophos Anti-Virus for Mac

What is the AV doing?

So anti-virus is basically a categorisation technology: you look at a file and decide whether it’s bad. The traditional view people have of an AV engine is that there’s a huge table of file checksums, and the AV product just compares every file it encounters to every checksum and warns you if it finds a match. That’s certainly how it used to work around a decade ago, but even low-end products like ClamAV don’t genuinely work this way any more.

Modern Anti-Virus starts its work by classifying the file it’s looking at. This basically means deciding what type of file it is: a Mac executable, a Word document, a ZIP etc. Some of these are actually containers for other file types: a ZIP obviously contains other files, but a Word document contains sections with macros in which might be interesting. A Mac fat file contains one or more executable files, which each contains various data and program segments. Even a text file might actually contain a shell script (which could contain a perl script as a here doc), and so on. But eventually the engine will have classified zero or more parts of the file that it wants to inspect.

Because the engine now knows the type of the data it’s looking at, it can be clever about what tests it applies. So the engine contains a whole barrage of different tests, but still runs very quickly because it knows when any test is necessary. For example, most AV products now including Sophos’ can actually run x86 code in an emulator or sandbox, to see whether it would try to do something naughty. But it doesn’t bother trying to do that to a JPEG.

That sounds slow.

And the figures seem to bear that out: running a scan via the GUI can take hours, or even a day. A large part of this is due to limitations on the hard drive’s throughput, exacerbated by the fact that there’s no way to ask a disk to come up with a file access strategy that minimises seek time (time that’s effectively wasted while the disk moves its heads and platters to the place where the file is stored). Such a thing would mean reading the whole drive catalogue (its table of contents), and thinking for a while about the best order to read all of the files. Besides, such strategies fall apart when one of the other applications needs to open a file, because the hard drive has to jump away and get that one. So as this approach can’t work, the OS doesn’t support it.

On a Mac with a solid state drive, you actually can get to the point where CPU availability, rather than storage throughput, is the limiting factor. But surely even solid state drives are far too slow compared with CPUs, and the Anti-Virus app must be quite inefficient to be CPU-limited? Not so. Of course, there is some work that Sophos Anti-Virus must be doing in order to get worthwhile results, so I can’t say that it uses no CPU at all. But having dealt with the problem of hard drive seeking, we now meet the UBC.

The Unified Buffer Cache is a place in memory where the kernel holds the content of recently accessed files. As new files are read, the kernel throws away the contents of old files and stores the new one in the cache. Poor kernel. It couldn’t possibly know that this scanner is just going to do some tests on the file then never look at it again, so it goes to a lot of effort swapping contents around in its cache that will never get used. This is where a lot of the time ends up.

On not wasting all that time

This is where the on-access scanner comes in. If you look at the Sopohs installation, you’ll see an application at /Library/Sophos Anti-Virus/InterCheck.app – this is a small UNIX tool that includes a kernel extension to intercept file requests and test the target files. If it finds an infected file, it stops the operating system from opening it.

Sophos reporting a threat.

To find out how to this interception, you can do worse than look at Professional Cocoa Application Security, where I talk about the KAUTH (Kernel AUTHorisation) mechanism in Chapter 11. But the main point is that this approach – checking files when you ask for them – is actually more efficient than doing the whole scan. For a start, you’re only looking at files that are going to be needed anyway, so you’re not asking the hard drive to go out of its way and prepare loads of content that isn’t otherwise being used. InterCheck can also be clever about what it does, for example there’s no need to scan the same file twice if it hasn’t changed in the meantime.

OK, so it’s not a resource hog. But I still don’t need anti-virus.

Not true. This can best be described as anecdotal, but all of the people who reported to me that they had run a scan since the free Sophos product had become available, around 75% reported that it had detected threats. These were mainly Windows executables attached to mail, but it’s still good to detect and destroy those so they don’t get onto your Boot Camp partition or somebody else’s PC.

There definitely is a small, but growing, pile of malware that really does target Macs. I was the tech reviewer for Enterprise Mac Security, for the chapter on malware my research turned up tens of different strains: mainly Trojan horses (as on Windows), some OpenOffice macros, and some web-based threats. And that was printed well before Koobface was ported to the Mac.

Alright, it’s free, I’ll give it a go. Wait, why is it free?

Well here I have to turn to speculation. If your reaction to my first paragraph was “hang on, who is Sophos?”, then you’re not alone. Sophos is still a company that only sells to other businesses, and that means that the inhabitants of the Clapham Omnibus typically haven’t heard of them. Windows users have usually heard of Symantec via their Norton brand, McAfee and even smaller outfits like Kaspersky, so those are names that come up in the board room.

That explains why they might release a free product, but not this one. Well, now you have to think about what makes AV vendors different from one another, and really the answer is “not much”. They all sell pretty much the same thing, occasionally one of them comes up with a new feature but that gap usually closes quite quickly.

Cross-platform support is one area that’s still open, surprisingly. Despite the fact that loads of the vendors (and I do mean loads: Symantec, McAfee, Trend Micro, Sophos, Kaspersky, F-Secure, Panda and Eset all spring to mind readily) support the Mac and some other UNIX platforms, most of these are just checkbox products that exist to prop up their feature matrix. My suspicion is that by raising the profile of their Mac offering Sophos hopes to become the cross-platform security vendor. And that makes giving their Mac product away for free more valuable than selling it.

Rumors of your runtime’s death are greatly exaggerated

This is supposed to be the week in which Apple killed Java and Flash on the Mac, but it isn’t. In fact, looking at recent history, Flash could be about to enter its healthiest period on the platform, but the story regarding Java is more complicated.

Since releasing Mac OS X back in 2001, Apple has maintained the ports of both the Flash and Java runtimes on the platform. This contrasts with the situation on Windows, where Adobe and Sun/Oracle respectively distribute and maintain the runtimes. (Those with long memory will remember the problems regarding Microsoft’s JRE, which was eventually killed by court injunction.) In both cases, Apple has received occasional chastisement when its supported version of the runtime lagged behind the upstream release.

In the case of Flash, this was always related to security issues. Apple’s version would lack a couple of patches that Adobe had made available. However, because Adobe maintains the official runtime for Mac OS X, it’s super-easy to grab the latest version and stay up to date. If Apple stops maintaining its sporadically-updated distribution of the Flash runtime, then everyone who needs it will be forced into grabbing a new version from Adobe (who are free to remind users to install updates as other third-party vendors do). Everyone who doesn’t need it doesn’t have the runtime installed, thus reducing the attack surface of their browsers. Win-win.

Java, as I mentioned, is a more complicated kettle of bananas. Apple isn’t redistributing the upstream JRE in this case, they’re building their own from upstream sources. While other runtimes exist, none integrates as well with the OS due to effort Apple put in early on to support Yellow Box for Java and Aqua Swing. This means that you can’t just go somewhere else to get your fix of JRE – it won’t work the same.

There isn’t a big market of Java apps on the Mac platform, so there isn’t a big vendor who might pick up the slack and provide an integrated JRE. Oracle support OpenOffice on the platform, but that isn’t a big earner. There’s IBM with their Lotus products – I’ll come onto that shortly. That just leaves the few Java client apps that do matter on the Mac – IDEs. As a number of Java developers have stated loudly this week, there are many Java developers currently using Macs. These people could either switch to a different OS, or look to maintain support for their IDEs on the Mac: which means supporting the JRE and the GUI libraries used by those IDEs.

By far the people in the best position to achieve that are on Eclipse. The Eclipse IDE (and the applications built on its Rich Client Platform, including IBM’s stuff mentioned earlier) use a GUI library called SWT. This uses native code to draw its widgets using real Cocoa (in recent versions anyway – there’s a Carbon port too) so SWT already works with native drawing in whatever JRE people bring along. This SoyLatte port of OpenJDK can already run Eclipse Helios. Eclipse works with Apache Harmony too, though the releases lag behind quite a bit.

So the conclusion is that your runtime isn’t dead, in fact its support is equivalent to that found on the Windows platform. However, if you’re using Java you might experience a brief period in the wilderness unless/until the community support effort catches up with its own requirements – which aren’t the same as Apple’s.