Solipsism Gradient

Rainer Brockerhoff’s blog

Browsing Posts published in March, 2008

Mike Ash recently posted about code signing. We’d talked about the subject a few days before and that is a great summary of Mike’s thoughts about it.

Code signing on Mac OS X is still evolving, but with the release of the iPhone SDK, the subject is suddenly being thrust into the limelight. To quote the Wikipedia article:

Code signing is the process of digitally signing executables and scripts to confirm the software author and guarantee that the code has not been altered or corrupted since it was signed by use of a cryptographic hash.

In the past, code signing has been used on several platforms with differing intents and implementations; Microsoft, for instance, has a driver signing program that lets only Microsoft-certified device drivers run without warnings on Vista. In contrast, here’s a statement from an Apple engineer on the apple-cdsa mailing list:

Windows “code signing” is not only completely different in design and implementation, it also has a completely different *intent*. The Windows version tries to determine whether *Microsoft* thinks your program (or driver etc.) should be used. Mac OS X Code Signing is a general medium to let the manufacturer and user negotiate as to whether/how they want to trust each other, with the system providing the infrastructure to make this possible.

From what I’ve learned about the subject so far, the Mac OS X implementation seems indeed to be aimed in this direction – there’s very little documentation available. Even less is, of course, available for the iPhone OS implementation, and details are under NDA. But let me try to explain what I learned so far.

Mac OS X code signing is an implementation of the X.509 standard public key infrastructure. It depends on a cryptographical algorithm which gives reasonable assurance that signatures cannot be forged with currently wide-available technology. Of course that’s a rapidly moving target, and the twiddly mathematical details are beyond the scope of this post (and, in parts, of my poor brain too).

So, you can have signed executables (single binary files) and signed bundles (which can applications, frameworks, plug-ins and so forth). A signed bundle is easily distinguished by the presence of an extra “CodeResources” file inside the bundle’s Contents folder. This file is a XML file containing, among other data, a dictionary that contains a hash code for every file inside a bundle. It also has a list of “optional” files or folders; this allows you to remove things like unwanted localizations from an application without invalidating the signature. Of course, if you later re-add a localization its hash codes must match the one inside the file. Additionally, a signature is added to the bundle’s executable.

If you check Mac OS X’s system folder and applications, you’ll find that, beginning with Leopard, every framework, application and command-line tool is signed. This signature, by various convoluted means, is checkable (currently only by Apple’s codesign command-line tool). It also points back at Apple’s “root certificate“. This certificate is is a component in X.509’s chain of trust tree, which basically tells you which authorities certify that a particular signature is valid; in effect, when you reach the root of such a tree you have to decide whether the root certificate can be trusted. (X.509 also can be used for distributed, or peer-to-peer, trust networks.) Let’s see how you can check this in practice. Open Terminal and try this:

$ codesign -vvvv /Applications/
/Applications/ valid on disk
/Applications/ satisfies its Designated Requirement

(as usual, type the line after the $ prompt and you should see the resulting lines.)

So this means that the Safari application is signed and its signature is intact. Otherwise, you’d get either a “code object is not signed” message, or if the signature has been tampered with, a “code or signature modified” message. Now let’s try a small variation on the command:

$ codesign -dvvvv /Applications/
Format=bundle with Mach-O universal (i386 ppc7400)
CodeDirectory v=20001 size=7621 flags=0x0(none) hashes=375+3 location=embedded
Signature size=4064
Authority=Software Signing
Authority=Apple Code Signing Certification Authority
Authority=Apple Root CA
Info.plist entries=23
Sealed Resources rules=9 files=283
Internal requirements count=1 size=68

This gives more information. Specifically, we see that there are 3 “certification authorities” included into the signature, and that there is one “internal requirement”. To see this requirement, try:

$ codesign -dr- /Applications/
host => anchor apple and identifier ""
# designated => identifier "" and anchor apple

This is admittedly hard to wrap your neurons around. From what I understood, the “requirements” are actually a little language that establishes what conditions the signed bundle should satisfy. But satisfy to able to… what? Now there’s where everything is (on purpose) still a little vague. “anchor apple” apparently means that the basic requirement is that Apple’s root certificates be present and trusted. Open the Keychain Access utility, click on “certificates”, and you’ll see somewhere in the list a certificate called “Apple Root Certificate Authority”. You can double-click on it to see details.

But what is all this useful for? Your proverbial “Aunt Tillie” will certainly not be interested in typing commands into Terminal, following certificate chains, and reading up on trust audit procedures. Apple’s keychain software tries to make all that as transparent as possible. Simply logging into Mac OS X can open parts of the keychain, and when Aunt Tillie goes to her banking site, the bank’s certificate should be checked against the keychain’s certificates and with the issuing certification authority, and everything should “just work”. For that to be reliable, Safari’s code signature should also be checked – otherwise it could be hacked by some malicious entity to say that the bank’s site checks out OK even when it’s some phishing site masquerading as that bank!

Signatures and certificates are also checked by the parental control preference panel, by Mail when it receives signed e-mail, and so forth. You may be familiar with the dialog asking if a recently-updated application may access the keychain to store or retrieve passwords; for signed applications, this dialog will be issued only once. If a newly-installed update has the same signature as the previous version, which had already been authorized to access the keychain, it’s assumed to also be trusted to do so.

A similar scenario applies to critical code such as the codesign executable itself. Ideally, such code should refuse to run if it’s modified; Apple has some facilities already in place to do so, and even to detect if an executable ihas been modified while it’s already running by some malicious code injection. However, that sort of thing isn’t widely used yet; mostly because it would break certain facilities, like Input Managers, that people currently rely on.

One aspect I haven’t touched upon yet is the so-called “self-signed certificate”. This is a certificate which is its own root certificate, like the top certificates of the various ‘big” authorities. The difference is that these authorities are large companies that undergo serious auditions and verifications. As an example, Quay is currently self-signed; I’m still evaluating how to publish my certificate in a way that easily allows my users to check if new versions have indeed been signed by myself. Let’s run one of the same verifications on Quay:

$ codesign -dvvvv -r- /Applications/
Format=bundle with Mach-O universal (i386 ppc)
CodeDirectory v=20001 size=245 flags=0x300(kill,hard) hashes=6+3 location=embedded
Signature size=1671
Authority=Rainer Brockerhoff
Signed Time=Mar 8, 2008 08/03 22:28:09
Info.plist entries=14
Sealed Resources rules=4 files=18
host => anchor apple and identifier ""
# designated => identifier "net.brockerhoff.Quay" and anchor leaf = H"4cbb97c74336f7ee6aa566122a5e7688e1c725dc"

See the difference? It shows only my name as authority, and a SHA1 hashcode at the end. I could publish this hashcode on my site and it would be not too difficult for a technically knowledgeable user to verify that his copy of Quay matches that.

What does this really mean? Actually, not too much. It means that two versions of Quay that give identical names and hashcodes, which additionally match the ones published on this site, giving reasonable assurance that the author of both versions and of the site are the same; but nothing at all beyond that. However, there are ways around that – SHA1 hashcodes can be duplicated with some effort, though perhaps not yet for certificates, and this site doesn’t have a secure (https) variant. A malicious person could easily strip away my code signatures, resign everything with a new self-signed certificate using my name, make a phishing site that looks like mine, and so forth, and to a normal user everything would appear to be OK. Would someone do that for a €7 utility program? Very probably not worth the trouble, but you can’t be sure.

Then again, I could invest in a secure site, an official certificate signed by a trusted authority – perhaps even by Apple itself – and all that would just make the code signature itself more reliable; it wouldn’t necessarily correspond to what extent the code itself can be trusted to always “do the right thing”.

As Mike points out, there’s a huge gap between “signed” and “trusted”. Ultimately you have to trust somebody, or you would be too scared to buy a box at a computer store and open it, much less connect that computer to the Internet or let your children touch it. If I buy a certificate from Apple, and use that to sign my code, you have to trust someone in the certificate chain even if my code seems to “just work”… it wouldn’t necessarily mean that Apple has audited and quadruple-checked my source code. Indeed, it doesn’t even touch the question of whether Apple as a company can be trusted!

All that is still largely theoretical; Mac OS X still runs unsigned code with no problem, even though with some small restrictions regarding use of the keychain, the firewall, and internet access as I mentioned above. But Apple engineers say that in the future code signing will become mandatory. In the next post, I’ll try to discuss the implications of that – especially regarding the upcoming iPhone OS 2.0, where it will be mandatory from the outset.

Forgot to link to Macworld’s iPhone FAQ, which also tries to answer many questions about the business aspect.

To sum up, anyone can register as a developer and run applications on the included “Aspen” simulator. However, to run your app on an actual iPhone or iPod Touch, you need to invest $99. This gives you a code signing certificate that will be attached to your applications. I’ll post more about code signing later, but in essence this certificate is a code that uniquely identifies you (the developer) and is tied to Apple’s master certificate. It’s not counterfeitable by current technology. Whenever some software is executed by the iPhone, the system first checks its signature. If it’s not signed, it won’t run at all. If it is signed, the certificate will be either Apple’s own – in which case the software presumably will have full access to all system functions – or it will be a “normal” developer certificate. In that case, the application will be allowed to run with restrictions inside a sandbox – a separate folder contain the application and its data.

Once your application is tested, you must send it to Apple to be considered for inclusion into the App Store. This is a central marketplace that will be accessible directly from the iPhone or from iTunes. Apple may not approve your application; some broad guidelines were mentioned, and hopefully will be clarified before the store goes online by the end of June (after WWDC). In any event, approved or not, you’ll have no alternative way of distributing; both iTunes and the iPhone OS will only load new applications from the App Store. Presumably approved applications will have a stronger certificate which is checked at installation time, and which can be remotely revoked by Apple if your application is latter deemed to be “untrusted”.

One particular “forbidden” application type is one that downloads and runs plugins, interpretable or executable code from elsewhere. Of course that can’t be taken too literally, or it would exclude (for instance) JavaScript on a web page. Still, it would at first glance forbid Java; even so, Sun has announced intentions to produce a free Java virtual machine for the iPhone. No word yet from Apple about that, but you can presume that all those rules will have exceptions whenever Apple considers it convenient to make them.

For “indie” developers like myself, the App Store seems to be a good idea. You get 70% of the sales price. Free apps are allowed, too. In comparison, I get 85 to 90% of the sales price in my current arrangements for Mac software – but I spend some of that difference on bandwidth, site maintenance, and customer support. I personally spend almost nothing on marketing and advertising, but some developers do spend more. The App Store idea is that Apple takes care of all the business details for you, and it’s not an unreasonable deal.

Many people are discussing the implications of consenting to Apple’s rules in order to being allowed to publish iPhone applications. Personally, I’m not too bothered. Like any finite game, you can consent to play or not, but once you do, you have to play within the rules.

Speaking of rules, some of them are none too clear yet. It seems that publishing a free version that is unlocked by a serial number, as we’re used to, is not allowed as such; I suppose you’ll have to do a free version and a paid update. How would I send my app to another user for beta-testing? Unless that user also has the SDK and a certificate, and if I’m willing to send over my source, that seems to be impossible. For now, I suppose you can compile a simulator version and send the object code to some other SDK user; good for checking out the user interface maybe, but not a real-world test.

Support is also tricky. Will Apple do support for all the apps? I doubt it. If someone emails you with a support request, how can you, since there are no serial numbers, check that the request comes from a legitimate user? And you can’t send out a special version for testing, either. Hopefully Apple will explain this soon.

Next: code signing.

Update: forgot to explain the $99. This appears to be an annual fee, much like the $500 I pay now every year for the “ADC Select” program. Does this mean that the developer certificates expire after a year? Well possible, but will that also affect applications already on the App Store? More questions…

Well, there’s little actual information to add to Gruber‘s and TidBITS usual comprehensive write-up, but maybe I can explain some parts in more detail, or provide an opinion on how this will impact developers in the future.

Regarding SDK details as such, most of it is under NDA, which I signed yesterday; but some details have been published already. It’s common knowledge that it includes Xcode 3.1, which will very soon be available as an independent (and free) download, and of course included on installation DVDs with any Mac as soon as it gets out of beta. It also includes Interface Builder 3.1 but not the special objects to directly build iPhone windows; this will no doubt follow in the next release.

I was looking forward to getting my hands on the iPhone UI – to date, I haven’t seen one in the flesh (same for the iPod Touch). But fortunately the simulator includes Safari, so at least I can check how this site looks; some pages come in too wide, and I’ll tweak them as soon as I find time. Still, the UI for the few included apps looks great and it’s useful to get a feel for all the animations. Speaking of the simulator, it’s not a hardware-level simulator; it seems to run x86 code, no doubt an easy way to make it even harder for hackers to glean information about the actual iPhone OS implementation.

I suppose this would also explain why the current SDK is Intel-only; the PowerPC version might not have made it in time, or may be too slow, or whatever. Still, it’s a bad precedent. Intel Macs seem to be about 50% of the installed base by now, a year before I thought that would happen, but it’s still too soon for people to stop doing Universal applications. For what it’s worth, I had to install everything on the only Intel Mac I have – a Core Solo mini with 512MB RAM – but it seems to run quite well despite the cramped hardware.

This “iPhone OS” name now seems to be the new “OS X” and it’s… clumsy. Not a good way to indicate a new platform that already includes the Touch and before the end of this year (or so I think) will get new members. Indeed, there are hints that both “mobile” and “touch” were at one time or another the platform name du jour, and hopefully this will prove to be just a beta name.

Certainly nobody in the Mac developer community was surprised that the SDK is based on Xcode, Cocoa and Objective-C; doing otherwise would mean a complete rewrite of the current 1.1.x firmware, and Apple hasn’t enough manpower to pull such a thing off. Besides, it’s certainly a good way to get Macs into the hands of new developers. Still, no doubt some people are miffed or surprised that the SDK doesn’t run in Visual Studio, or that there’s no Java or .NET support; I can imagine them complaining to Microsoft about this (hey, Microsoft owns a good chunk of Apple, or so they probably believe).

Next: the business part. That’s where it gets interesting.

I pushed Quay 1.1b3 out a few days ago and immediately had to quick-fix and slip in a new build (same version number) because of an endian issue on Intel Macs.

Yes, I should have tested this; for some reason, all people I asked to run preliminary builds also were on PowerPC Macs – including two I’d have sworn were on Intel. Murphy never sleeps. My own solitary Intel machine – a rock-bottom mini (Core Solo, 512MB) – had been down for almost a month, having had some indigestion with one of the last Leopard betas, and I finally spent an afternoon wiping it and reinstalling 10.5.1 on it (also seizing the opportunity to confirm that Qay still runs well, and with almost all features, on that version).

Curiously enough, this made me notice that two steps in my build chain (utilities that generate intermediary files) are still PowerPC-only and break when I build the project on an Intel machine. Must fix that because pretty soon I’ll have an Intel laptop available, and it must be able to do full builds.

I hope to have the next version out in the middle of next week. I’ve already fixed one issue – an oversight in the last rewrite made it stop working for folder aliases dragged directly into the Dock. There are a smaller bugs outstanding, but nothing too serious. Unless something turns up that requires serious testing in the field, the next release will (I hope) be 1.1 final.

Quay is the first software I wrote from the outset to be localized. Once you take some precautions this is relatively easy to do in a Cocoa application, and I’m talking to Ronald Leroux, a well-known localizer for French, to see whether we can get a pilot French version in time for 1.1. There are a few obstacles; I’m used to fiddling around with text right until the last minute; current localization software isn’t quite working yet for the new-fangles nib files used by Leopard/Xcode3; and code signing proves to be an unexpected puzzle.

Well, of course I can put all the current localization into the application bundle and sign it, and everything will “just work”. However, 99.9% of users will use only one of the included languages and some of those would be happy if no others were present. Code signing (at least the standard way which I’m using) doesn’t like files or folders removed from the application, nor does it like added items. It would indeed be nice if the various languages were present on the installation disk image but the user should be able to opt only for the currently enabled language, for instance. And it would also be nice be able to download additional or new languages as they become available.

I do have some ideas for workarounds to that issue, but I’m not sure they’ll work in time for next week’s release – be it 1.1b4 or 1.1 final. In any event I’m very anxious to finish off 1.1, as I’ve got serious plans for 1.2; a new GUI is only one aspect of that. Stay tuned.

Update: regarding localizations and signing, Mike Ash just reminded me that you can remove localizations without messing up the signature, but you can’t add new ones. I found out, however, that you can put a new localization somewhere outside the application bundle and then add a symlink from the resources folder from there. Interesting.

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