Share Extension Iterations

iOS, Mac, Workflow, Xcode

One of the many big surprises at WWDC this year was the news that iOS 8 and Mac OS X 10.10 would support app extensions, which give developers a variety of new ways in which data and services can be shared between apps.

One of these new types of extension, called a Share extension, essentially allows apps that generate user data provide content to apps that publish user data. As a developer whose main app, MarsEdit, is a blog-publishing tool for the Mac, you can imagine how this might be of interest to me.

The first thing I noticed upon digging into app extension development is that it’s fairly fiddly to get set up, and the default build, run, invoke iteration loop is fraught with administrative overhead.

First of all, when you add a Share extension target to an existing project, you’ll discover that the new target can’t be run directly. To test or debug it, you have to invoke the Share extension from some app that supports … sharing. There are many default apps on the Mac and iOS that support sharing data of various formats. For example on Mac OS X the system Preview app makes a canonical sharing source for photo data, while the Notes app is one of many suitable test apps for sharing text. If you don’t do anything special after adding a Share extension target to your project, the auto-generated Xcode scheme will be configured to ask every time you run:

ChooseAnApp

This will get old fast, and 99% of the time what you’ll want to run is exactly the same dang app you just ran. Luckily, this is easily addressed in the scheme settings, where you can change the “Executable” selection in the “Info” section of the “Run” tab from “Ask on Launch” to a specific application of your choosing.

OtherApp

That’s all well and good, but you still have to go through the tedious task of selecting some suitable content in the target app, clicking the share button, and choosing your extension from the list, before you even have the luxury of examining your own code’s behavior.

Wouldn’t it be great if you could make changes to your app extension’s appearance or behavior, click Run, and moments later be looking at your Share extension’s UI without having to do anything else? Good news: you can, and I’m about to explain how to achieve it for both Mac and iOS targets.

Automatic Invocation

The problem with all the targets on your Mac or iOS that may or may not support sharing pertinent data to your extension, is you have to walk them through the process of invoking you. When you’re deep into the development of a particular aspect of the user interface or mechanical behavior of your extension, what you really want is to repeatedly invoke the extension with the same, predictable kinds of data. Luckily, it’s possible on both Mac and iOS platforms for a host app to invoke sharing extensions programmatically, so you just need to choose a Run target that will predictably invoke your extension upon launching.

The only way I know to guarantee this is to write your own code that invokes the extension, and put it in a custom debugging-purposed target, or else put it into your main app as conditional code that only runs when building Debug variants and when prompted to take effect. I can imagine a sophisticated version of this approach involving a multi-faceted extension-debugging target that would be capable of fast-tracking extension invocation for a variety of data formats. But for the simplest solution, I recommend adding the ability to invoke your extension to the very app that hosts it. Then your simple test mode behavior will always coexist in the same source base as your extension code.

The way I approached this was to add an environment variable, “RSDebugAppExtension” to the scheme configuration for my app extension, which is also configured now to target the main app as its Executable target. So when I build and run the app extension scheme, may main app runs with these environment variables set:

Screenshot 11 24 14 3 12 PM

Now in the main app’s applicationDidFinishLaunching: method, I just have to add the appropriate code for invoking the app extension’s UI. Without the platform-specific voodoo, it looks something like this:

#if DEBUG
	// Check for flag to invoke app extension
	NSDictionary* env = [[NSProcessInfo processInfo] environment];
	NSString* appExtensionDebug = [env objectForKey:@"RSDebugAppExtension"];
	if (appExtensionDebug != nil)
	{
		// RUN MY EXTENSION
	}
#endif

The #if DEBUG just ensures that I will never inadvertenly ship this code in a release version of my app. The environment variable ensures I won’t be plagued by my extension’s UI appearing whenever I’m working on other aspects of my app besides the extension.

Now we just have to dig into the specifics of how to “RUN MY EXTENSION.” I’ll show you how that works for both Mac and iOS based Share extensions.

Invoking a Mac-based Share Extension

If you’re working on a Mac-based Share extension, the key to invoking it at runtime is to enlist the help of the NSSharingService infrastructure. You simply ask it for a service with your identifier, and ask it to “perform.”

NSString* serviceName = @"com.red-sweater.yeehaw";
NSSharingService* myService = [NSSharingService sharingServiceNamed:serviceName];
[myService performWithItems:@[@"Hello world"]];

Now when I build and run with the aforementioned environment variable set up, it pops up my Share extension, pre-populated with the text “Hello world.”

Invoking an iOS-based Share Extension

Unfortunately, iOS doesn’t support the same NSSharingService infrastructure that the Mac has. This seems like an area where we might be lucky to see more unification over the years, but for the time being the iOS notion of a sharing service is tied up with the existing “Social.framework” and its SLComposeViewController class. This is the interface that is supposed to be used to invoke a sharing panel for Facebook, Twitter, Tencent Weibo, etc. And luckily, although I don’t believe it’s documented, you can also pass in the extension identifier for your custom Share extension to instantiate a suitable view controller for hosting your extension:

NSString* serviceName = @"com.red-sweater.yeehaw";
SLComposeViewController* myController = [SLComposeViewController composeViewControllerForServiceType:serviceName];
[myController setInitialText:@"Hello World"];
[[self navigationController] presentViewController:myController animated:YES completion:nil];

You can see the basic gist of it is similar to the Mac, but you have to configure the view controller directly as opposed to providing a list of arbitrary input values. Also bear in mind that because the iOS-based solution above relies upon [self navigationController] being non-nil, you’ll need to add the special debugging code at a point in your app’s launch process when this is already set up, or else find another way of ensuring you can meaningfully present view controllers to your app’s main window.

Going Further

Notice that I hinge all the invocation on simply whether the RSDebugAppExtension environment variable is non-nil. Basically while I’m debugging I have to go in and change the code in applicationDidFinishLaunching to invoke the extension in the way I want. This works OK for me at least at this stage, but I can imagine down the road wanting to be able to fine-tune the behavior of how the extension is invoked. For this purpose, why not encode into the value of the environment variable itself certain clues about how to invoke the extension? It could specify for example what text should be passed the extension, or other configuration as desired.

My intent in sharing this blog post is both to point out some potentially time-saving tricks that will help those of you developing Share app extensions, but also to encourage you to look for creative ways to cut out the tedious aspects of whatever you work on. When all is said and done, the few monotonous steps during each iteration of work on a Share extension probably don’t add up to all that much in sheer time, but they take a lot of the joy and immediacy out of development, which frankly puts me in a bad mood. Clicking Run and seeing my work, including my latest changes, pop up instantly on the screen makes me feel a lot happier about my job.

Burn After Releasing

Cocoa, Mac, Xcode

I am pretty diligent about following up on crash reports, probably because when it comes down to it, chasing crashes is one of the funner aspects of software development to me. Sure, when I’m hours into a frustrating problem and can’t make heads or tails of why something’s blowing up, it’s exhausting, and I wish to hell I could simply find the solution, but upon finally unwinding the riddle of a failure, it’s all those hours of toil that pay back dividends as the thrill of success.

Recently I had an odd MarsEdit crash report come in with a brief but ultimately very meaningful comment attached to it:

“I just updated a post with a PDF embedded from OneDrive.”

I love it when customers take the time to write something about the circumstances surrounding a crash. Often even a little clue can be enough to lead to the unique series of steps that will ultimately reproduce the problem. In this case though, I was confused. I know OneDrive is Microsoft’s cloud storage solution, but is the customer uploading a PDF from their mounted OneDrive, or … ?

Luckily the customer in this case also left an email address, so I got in touch and, after a few rounds of zeroing in on the meaning of the expression “embedded from OneDrive,” I learned that the issue was specifically to do with pasted HTML source code that Microsoft offers to customers who wish to literally embed a OneDrive document into another web page.

So I created a OneDrive account, added a PDF document to my storage, copied the “embed code” for the item, and pasted it into a new MarsEdit post. To my great surprise and satisfaction, when I pressed Send and published the post to my blog, MarsEdit crashed with exactly the same stack trace as the customer had submitted.

Well, I’ll be darned.

Pointing The Finger

The stack trace in this case was pretty cryptic, and implied that a private Apple class, NSURLConnectionInternal, was crashing while trying to message what I could only assume was its delegate. Here’s the gist of the very tip of the crashing thread’s trace:

Thread 0 Crashed:: Dispatch queue: com.apple.main-thread
0  libobjc.A.dylib	objc_release
1  libobjc.A.dylib	AutoreleasePoolPage::pop(void*)
2  com.apple.CFNetwork  -[NSURLConnectionInternal _withConnectionAndDelegate:onlyActive:]
3  com.apple.CFNetwork	-[NSURLConnectionInternal _withActiveConnectionAndDelegate:]

Usually, when you see something like this where a thread is crashing while trying to release an object, the first thing to suspect is that you’ve screwed something up. Probably by over-releasing some object or neglecting to nil-out a delegate attribute when one of your objects is destroyed. But in the case of logs like this where the crash occurs with a backtrace that is separate from your own code’s control (it’s a run loop callback to Apple’s own networking code), it can be hard to trace it back to specific code in your app. In this case, I can tell by the NSURL clues that a network request is probably being serviced, but which one? And which object was its delegate? Luckily, the clue about OneDrive had led me to a working test case, so I could dig into this question with more care.

The first step I like to take is to hopefully separate the crashing issue from my own app’s code, by creating a stripped-down test app that exhibits the problem. If I couldn’t achieve that, then the bug probably did rest somewhere in MarsEdit, and if I could create such a test case, then the problem of poking at it to deduce what is going wrong is made much simpler.

I created a new document based application whose document windows possess a single WebView. When a new document is created, the document does one thing: load one of those OneDrive embedded documents as the HTML content of the view. Armed with this test app, I was able to create new WebView instanced with the presumably problematic HTML code, and observe the behavior of each WebView in isolation from other junk that might have been going on in a more complex app such as MarsEdit.

The only problem was that my test app didn’t seem to exhibit any problems. I could load 10, 20 WebViews with the OneDrive embed code in it, and they all ran like butter. Damn it, there was no bug here! Until, that is, I deigned to close one of those windows. Blam! The test app crashes, yielding an identical stack trace to the one provided by my customer and reproduced in MarsEdit.

It started to make sense: when you publish a post from MarsEdit, the default setting is to also then close the window associated with that post. The reason the customer experienced the crash after sending the post to their blog was only because that happened to correlate with MarsEdit subsequently closing the window, and thus destroying the WebView that had held the OneDrive embed content.

Whose Zombie Is This?

Armed with a simple test case that reproduces the bug at will, the first thing I did was to enable Apple’s built-in facility for debugging so-called “zombie” objects. These are perfectly named because they are objects that have been deallocated but which some code within your app treats as though they were still alive. When you message a zombie object, the behavior is unpredictable because all the data that had been associated with the object is now correlated with whatever other use the system has found for that area of memory. Xcode has a convenient checkbox that makes it easy to turn on zombie detection. Just open the scheme editor and look for the Diagnostics tab under the Run configuration:

Screenshot 11 6 14 5 25 PM

This option instructs the Objective-C runtime to abstain from completely deallocating objects. In doing so, it transforms deallocated objects into a special kind of placeholder object that can detect when it has been messaged, and scream to high hell about it. When I run with zombie objects enabled, and reproduce the crash, I also see this message in the console log:

*** -[WebView release]: message sent to deallocated instance 0x6080001273a0

Ah ha! So the object in question, the one being delegated to by NSURLConnection, is probably the instance of the WebView itself. But, I don’t set a WebView as a delegate of any NSURLConnection, and certainly this simplified test case doesn’t. So it must be WebKit itself that is setting itself as an NSURLConnection’s delegate. Not my problem, I can file the bug and move on … or can I?

Going The Extra Mile

This is where the open-sourced nature of WebKit is both a blessing and a curse. If this issue had been revealed to exist somewhere deep within AppKit, or any of Apple’s other closed-source frameworks, I most certainly would have thrown up my arms, filed a bug, and hoped for the best. But Apple’s WebKit framework is something I can download, build, and debug. Sure, it takes nearly all day to build, and there is a steep learning curve to debugging it, but why did I become a software developer if I’m not up for a challenge?

Since I knew that the issue at its core appeared to be the over-release of an object, specifically of the WebView, I moved up from the basic utility of zombie objects to the high-octane “Zombies” flavored analysis configuration of Apple’s Instruments tool. Like the runtime flag we set earlier in Xcode, this makes it easy to detect attempts to message zombie objects, but it also goes a step further by correlating that knowledge with a recorded history of a given object, and all the memory-management related manipulations of that object.

Simpler

The tail end of a very long table shows the running retain count for an object, in this case the WebView itself, as well information about which library, method, or function was responsible for the call that affected the object’s memory management status.

To make a long, long, long, long, story very short: I used Instruments and its “pairing” functionality, which lets you hide balanced pairs of retain/release calls so that you are left with a more manageable subset of calls to examine and scrutinize. After scratching my head over this for hours and not making much headway, I finally came upon a specific call stack that had a very suspicious heritage. I confirmed through Instruments and then by direct examination of WebKit source code, that the WebView instance in question was in fact retaining and then autoreleasing itself as part of its dealloc method.

In this era of ARC, some of you may not be so intricately familiar with Cocoa memory management to see at a glance why that’s a very bad thing. Here it is a nutshell:

  1. By the time an object’s dealloc method is done running, the object is gone. I mean, literally gone, or else being managed as a zombie object for debugging purposes.
  2. An object can be retained and released as much as you like, but if you’re already in the midst of dealloc’ing the object, it won’t make a bit of difference.
  3. Autoreleasing an object postpones release until a later time, when the active autorelease pool is released.
  4. Thus, autoreleasing an object in the midst of being dealloc’d guarantees that it will later be sent a release message. Oops, that would be bad. It could even cause a crash like the one we’re seeing…

How in the heck does WebView manage to autorelease itself as a consequence of dealloc’ing itself? And what unique relationship does that possibility have to the embedding of Microsoft OneDrive documents? I’ll try to be as brief as possible:

Microsoft’s OneDrive support installs JavaScript callbacks that run on a periodic basis, constantly fetching data from Microsoft’s servers via xmlHTTPRequest. The calls are made with such frequency that, especially while an embedded document is in the process of loading, there’s a good chance that closing a WebView and dealloc’ing it will catch Microsoft at a time when it thinks sending such a request is a good idea. The process of cleaning up the WebView has a side-effect of cleaning up the JavaScript runtime environment, and callbacks such as Microsoft’s might get one last chance to send a network request.

Sending the request would be fine, except for WebView’s own conscientious behavior which takes care to retain and autorelease itself whenever a new batch of network requests is made on its behalf. This guarantees that the WebView won’t disappear while an open request is running. But of course, it can’t make that guarantee when the WebView is in the process of being destroyed.

Short story shorter: WebView inadvertently adds itself to the autorelease pool when it’s on the verge of being destroyed, and subsequent release of that autorelease pool causes a zombie message to be sent to the deallocated instance.

I reported the bug, and submitted a patch to the WebKit team. My proposed fix works around the problem by wrapping the bulk of WebView’s -dealloc method with a separate autorelease pool, such that any inadvertent autoreleasing of the WebView will be tidied up before the object is literally destroyed. Because WebKit is open source, I was able to make the change, build and test it, and confirm that the crashes disappear both in my test app and in MarsEdit.

I would like to thank Alexey Proskuryakov for taking the time to help dig into the issue in parallel with me. He was on to the nut of the problem long before I was, but I glossed over some key hints in his analysis. He also helped in guiding me through the steps of submitting a proper patch with my bug report.

In The Mean Time

Hopefully Apple will accept my patch, or come up with a smarter way of fixing the problem for a future update to WebKit. In the mean time, I want my app to be as reliable as possible for the widest variety of users as possible. Yes, that even means Microsoft OneDrive users. How can I work around the problem today?

The simplest solution, requiring neither subclassing of WebView, swizzling, or anything like that, is simply to take care before releasing a WebView in your app, to manually call -[WebView close] on it first. This takes care of all the complicated business that runs the risk of autoreleasing the WebView, such that when WebView’s own dealloc method is reached, it won’t have any such complexities to expose itself to.

Tracking down and fixing this bug has been an incredibly tiresome yet rewarding experience. I hope you have learned a thing or two from the approach I took here, and that I have inspired you to take crash reports with the seriousness they deserve. Your customers will thank you for it, and you might even get a kick out of occasionally coming out on top!

Yosemite’s Dark Mode

Apple, Cocoa, Mac

If you’re a Mac developer you’re no doubt feeling that restlessness that comes when a major new OS release is nigh. Mac OS X 10.10 Yosemite has been cycling through “GM Candidate” releases for the past couple weeks, and many people seem to think it’s likely to be released to the public later this month.

One of the big user-facing visual changes is an optional “dark mode,” accessible from the General tab of System Preferences. When a user ticks this on, high level UI elements such as the menu bar and dock adopt a different style of drawing which you can roughly characterize as being white-on-black instead of the default black-on-white Mac appearance.

One hiccup for developers of third party apps is if you have an NSStatusItem or other custom menu bar item with a custom icon, you probably designed it so that it looks good on the white or light default menu bar.

Unfortunately, Apple has not provided a sanctioned method for detecting whether the user has switched to “dark mode,” so it’s non-trivial to tune your art to suit each of the modes at runtime. Instead, Apple recommends that all such icons should be designed such that Apple can effectively color them as appropriate for the current mode.

Luckily it’s pretty easy to get this behavior for custom status bar icons. You probably already call -[NSStatusItem setIcon:yourImage] with your custom image. Now, just make sure to call -[yourImage setTemplate:YES], and you’re done. The only caveat I would add here is that Mac OS X 10.9 and earlier do not seem to respect the “template” attribute when drawing status items, so I think the safest bet is to check for 10.10 at runtime, and omit the call to setTemplate if you’re running any earlier system:

BOOL oldBusted = (floor(NSAppKitVersionNumber) <= NSAppKitVersionNumber10_9)
if (!oldBusted)
{
	// 10.10 or higher, so setTemplate: is safe
	[myIcon setTemplate:YES]
}

Now your status item icon looks great on 10.10, where in fact its coloring may even be slightly altered in light mode, and in 10.9, where it looks, well, like it always did. Update: thanks to Rick Fillion and Will Cosgrove for explaining that my problems on 10.9 are probably because my image is not designed right for use as a template. I’ll leave the solution to that as an exercise for the writer.

Unfortunately, this promise does not hold true for regular NSMenuItem items that are installed at the highest level in the menu bar. These are relatively uncommon, but for example you might find some apps with a gear icon, a script icon, or other similar graphic in lieu of a text-based menu title. When an icon is supplied to such a menu item, the template nature is not meaningfully respected in dark mode, so the icon draws more or less as-is, and is likely to almost disappear because of the lack of contrast. If you happen to be running 10.10 you can witness this problem by running iTunes and seeing that at least one script is in ~/Library/iTunes/Scripts. Its script menu icon appears right next to the “Help” menu.

I reported the issue to Apple and it came back as a duplicate. As of the latest 10.10 GM candidate, it has not been fixed, but I got a reassuring tweet from Apple’s own Eric Schlegel today:

So in summary, if you use icons as the “titles” of menus either inside or outside of the status bar area of the menu bar, be sure to call setTemplate:YES on it when running on 10.10. If you happen to have a menu bar icon affected by the bug I reported, I recommend creating a test project that installs an NSStatusItem with the same icon, so you can get a sense for how it’s going to look in dark mode when its template nature is suitably handled.

What To Do About Code Signing

Apple, Mac, Xcode

I wrote about the confusion arising from Apple’s poor communication about new code signature requirements, and then just earlier today I wrote about the revelation that many apps have been reprieved by an Apple whitelist.

I tend to write long, so let’s cut to the chase: what do you need to do if you are a Mac developer who ships software directly to customers or via the Mac App Store?

  1. You must ensure your next software release is signed with a Version 2 code signature. The easiest way to do this is to build and sign your product on Mac OS X 10.9 or later.
  2. You must test your existing, published apps to see that they can be downloaded and opened without issue on 10.9.5 and 10.10. To be safe, try to test once from a machine/install that has never seen the app before. If you’re concerned, read the details in my previous posts to assure yourself that your existing app was whitelisted.
  3. If your existing app does not open or in particular if it receives an “obsolete resource envelope” assessment from the “spctl” tool, you must either release a new version of your app signed with a Version 2 code signature, or re-sign your existing app. Otherwise, people who download the app will be greeted by a warning that the software is “not trusted.”

That’s it, folks. Everybody has to start signing with the modern code-signing infrastructure. In the interim, there’s a good chance your app has been whitelisted to operate as usual during the transition, but that courtesy will probably not extend to your next release.

Gatekeeper’s Opaque Whitelist

Apple, Mac

I wrote previously about the confusion that arose when many developers, trying to comply with Apple’s new code signing rules, ran across strange system behavior in which version 1 signatures seemed to work, yielding the curious system policy message “accepted CDHash.”

I can’t believe I didn’t think until now to check Apple’s open source Security framework for clues about this. Poking around today I found something very curious. In the policyengine.cpp source file, search for “consult the whitelist” and you’ll find the clump of code that very deliberately avoids rejecting an app for its “obsolete resource envelope” if it passes some whitelist check:

if (mOpaqueWhitelist.contains(code, rc, trace))
	allow = true;

Well I’ll be darned. Could this explain the fact that many, many people observed that their apps with old, V1 signatures continue to pass Gatekeeper’s scrutiny e.g. on 10.9.5, even though Apple stated that V2 code signatures would be required?

The whitelist database is stored on your Mac in the following location:

/var/db/gkopaque.bundle/Contents/Resources/gkopaque.db

Go ahead, poke around at it. It’s big! It will be a bit easier to play with if you have any experience at all using the sqlite3 command line tool. With it, for example I was able to discover that there’s a table called “whitelist” within it, and that it contains two columns: “current” and “opaque”. And there are a LOT of rows in the table:

sqlite> select COUNT(*) from whitelist
68101

So what does a typical row from the table look like?

sqlite> select quote(current), quote(opaque) \
           from whitelist limit 1;
X'000327ECE1FB5A27B5F5C51A009900B1E4854BB7'|
X'CBE56B9784974E0A1C0159C41F392B77421B4D23'

By scrutinizing the code and poking around, I’ve determined that the “current” column is not unique, and corresponds to the “CDHash” of a given code object being analyzed. For example, a version of MarsEdit that shipped with a V1 code signature and which does not seem affected by the changes in Apple’s Gatekeeper policy has a CDHash of “D1FBA2AB9A4814877BE8C1D2A8615FB48D8D4026”, and on my system anyway there are two rows corresponding to that CDHash.

I don’t really get what the “opaque” column is about, and my ability to scrutinize Security source code isn’t great enough to easily be able to tell by reading the source, either. But it seems to me that it must somehow be a way of informing the security system that certain specific (possibly modified?) instances of an app are still essentially the same as the “current” CDHash being tested.

Using some more sqlite3 magic, we can determine the number of unique values in the “current” column:

sqlite> select count(distinct current) from whitelist;
36215

OK, I run a lot of software, but I’m quite positive I have not run 36K unique parcels of code in recent memory. My suspicion is that in the run-up to the major changes Apple has made to Gatekeeper, they painstakingly accumulated a list of 36215 “trusted” hashes and deposited them on everybody’s Mac so that the effect of 10.9.5’s stricter code signing checks would be mitigated.

One test I did to confirm that the database is not just a personalized list of the apps I have used, was to download an app that I don’t use regularly, Panic’s Unison, but that I thought would be popular and reputable enough to appear on Apple’s whitelist. I downloaded it, and before running it even once, I checked its CDHash (“35d9c847ebb7461aee5f08bb8e017b5a3891bc0f”) with the database. Sure enough, 7 rows match this CDHash. Perhaps accommodating 7 distinct releases of Unison? Again, I’m not sure. I then took the extra step of logging into another machine entirely, one which has never seen Unison even as a downloaded file. The database on that machine also contains the hash.

Want to see if your apps are “whitelisted” or not? It’s pretty easy to do from the Terminal:

  1. Find your CDHash by running “codesign -dvvv Your.app” and searching for the CDHash value in the output.
  2. Grep the database for your value: 
    sqlite3 /var/db/gkopaque.bundle/Contents/Resources/gkopaque.db "select quote(current), quote(opaque) from whitelist" | grep -i [yourCDHashHere]

This whitelist offers a significant amount of explanation as to why some apps are allowed to launch without issue on 10.9.5 and 10.10. I don’t understand the database completely, particularly the meaning of those “opaque” CDHash values in the second column, but I feel as though a lot of mysterious behavior on all of our Macs is suddenly a lot more understandable.

Update later on Oct 6: After publishing this entry, Ed Marczak chimed in on Twitter with some information about the database:

In other words, according to Ed, Apple gathered the list of “whitelisted CDHashes” by surveying the software that people actually run, and reporting that data to Apple in the form the unique code signature hashes. I’m not sure what criteria they applied in the end to decide which of those apps are included in the whitelist, but it sounds reasonable to assume that if nobody ran your app on 10.9.4, Apple did not have the opportunity to consider including you in the whitelist.

(Thanks to Jeff Johnson for talking through some of the discoveries that led to this post).

Fixing 90-Day Apple ID Expirations

Apple

I wrote a week ago that I was cautiously optimistic about a solution to a long-standing ordeal with my Apple ID password expiring every 90 days.

Today I got a very encouraging response from the Apple support representative who was shepherding the problem through to the engineering team that evidently knew how to fix the underlying issue with my account.

An update on the ticket I submitted to the Engineers states that you should now no longer receive those password reset prompts. Please contact us back referencing our case number: 663194617 if for any reason the issue persists after 90 days.

I have raised my cautious optimism to outright good cheer at the sight of evidence from Apple that “Engineering” saw a problem, claims to have fixed it, and both they and the support representative are confident about the solution. Furthermore, they offer a very special kind of 90-day warranty by inviting me to get back in touch for another round of effort should they be mistaken in their assessment.

I’ve been complaining about this issue on Twitter for such a long time and with such repetition that I’ve had the opportunity to hear feedback from tens if not a hundred or more people who have let me know that they too suffer the problem, and are eager to know of a solution. In the wake of last week’s post, at least one person was inspired to get in touch with Apple, only be to be shunted from Apple’s developer relations team to AppleCare, where I had previously failed to obtain any successful result.

As helpful as the representative was who helped me, I don’t feel comfortable sharing her name or direct contact information. But the fact that she seemed genuinely interested in solving this problem made me realize that it would be ideal if others who go down this path could stand at least a better chance of finding somebody as empathetic to the problem as she was.

So I asked her if she had any problem with me sharing my case number with “everybody on Twitter.” I didn’t exactly want to sic a mob of frustrated developers on Apple, but I do genuinely wish that everybody who has been as annoyed by this problem as I have will have a path of hope towards seeing it resolved. To my satisfaction she agreed enthusiastically with my proposition:

I don’t have an issue at all with you mentioning this case. I’d be more than happy for our group to help anyone in this situation if/when we can.

So in summary, this long journey has led me to a position where I now believe I can offer what is the most definitive set of instructions for developers with Apple Developer Connection accounts who would like to eliminate the annoying 90-day password resets:

  1. Go to the Apple Developer Program Support page.
  2. Select “Access Issues” from the Subject popup.
  3. Briefly explain the problem with your Apple ID password requiring a reset every 90 days, and reference my case #663194617 as a likely comparable issue which has been handled by developer support.

The fact that you’ll be in touch with a support staff that is empowered to consult with the pertinent engineering team, combined with the fact that they have persistent access to the documentation for my case will hopefully be a recipe that sets you up for the same success (finally!) that I have had.

Accepted CDHash

Apple, Xcode

A bit over a month ago, Apple announced big changes to the way Mac OS X versions 10.9.5 and 10.10 will recognize the code signatures of 3rd party applications, hinting very strongly that consequences would be dire for any developer neglecting to re-sign their apps:

Important: For your apps to run on updated versions of OS X they must be signed on OS X version 10.9 or later and thus have a version 2 signature.

Few details were given as to why the old signatures would no longer be respected, leaving developers with little to go on except to take Apple’s word that we should drop everything and update our code signing processes, which for some of us was a non-trivial amount of work. Those of us willing to grant Apple the benefit of the doubt assumed that there was some greater purpose to our collective suffering. Surely this nuisance is in the name of preserving or increasing security for all of Apple’s and our mutual customers.

That, and the fact that Apple stated bluntly that if we don’t make these changes, our apps will not pass Gatekeeper’s assessment and thus will not be allowed to launch without considerable work by users. This is an unacceptable user experience to any developer worth her or his salt, so of course the vast majority of us complied.

Some of us complied even when the logic of doing so was comically bent. For example Apple implied that developers of apps for the Mac App Store also needed to update their code signatures, in spite of the fact that all Mac App Store apps are signed by Apple, not by the original developers. The process of submitting software for sale on the App Store does include a code signing phase, but the signature is replaced by Apple before it is distributed to customers. So, if there is a security issue with version 1 code signatures, Apple is in a position to remedy the problem without the involvement of 3rd party developers. Some of us sought clarification from Apple on this point. Questions in the Apple Developer Forums along the lines of “do we really have to re-sign apps and submit a new version just to accommodate this new requirement?” were met by terse restatements from Apple along the lines of “all apps must be signed with version two code signatures.”

Sigh.

To make matters yet more confusing, a developer who has signed off on the chore of complying with Apple’s requests would not necessarily be able to verify the job was done right, because for example on pre-release builds of 10.9.5 and 10.10, many apps with “old and busted” version 1 signatures unexpectedly passed the system’s Gatekeeper check, contrary to the firm indication from Apple that they shouldn’t. Apple’s documentation provided a specific command to run from the Terminal that would verify or reject any specific app’s code signing:

spctl -a -t exec -vv Foo.app

For many of us with very old version 1 code signatures, the command line came back with a cryptic “accepted cdhash”, and the system happily opened and ran the apps without issue.

I reported the problem as a security bug because it seemed to suggest that apps with broken, insecure code signatures would still be allowed to run. I waited to see whether, with each subsequent beta release, Apple would finally ratchet things down to give me a taste of how customers would experience trying to run these apps with outdated signatures. But each beta release continued to allow them to run without incident.

Finally, a few days ago I got my bug sent back to me to be closed. Oh, they finally fixed it? Nope. It was returned with the classification “Behaves as intended.” Then yesterday, 10.9.5 shipped and lo and behold, contrary to every warning and veiled threat from Apple, many of these apps with old, version 1 code signatures, of the variety that yield a cryptic “accepted cdhash” assessment from the spctl tool, well, they just work. They’re fine. This happens to apply to my entire line of apps and this is probably also the case for many other developers. In short? I dropped everything, spent hours revising my code signing process, investigating unexpected results, contacting Apple for clarification, trying to make sense of Apple’s terse replies, and finally doing my best to comply regardless of doubt. And it turns out I didn’t actually have to lift a finger.

Which is not to say that nobody had to lift a finger. Any developer whose code signatures involved the use of “custom resource rules,” and (I think) any developer whose version 1 signature was signed with a new enough version of Xcode to escape the “accepted cdhash” loophole, but not new enough to be a “version 2” signature, did need to re-sign their apps.

This was a classic case of Apple communicating far too poorly about a situation that purported to affect potentially every Mac developer. Many of us spent way too much time trying to decode and make sense of the situation when Apple could have done so for us through careful clarification of the specific code signatures that needed updating, how they could be reliably verified, and what the actual consequences of inaction would be.

Cautious Optimism

Apple

For years I have been suffering a relatively benign yet still infuriating problem with my Apple ID: the password expires every 90 days, like clockwork, forcing me to choose a new one.

It sounds like a minor inconvenience, but it’s made somewhat worse by the fact that my Apple ID and its password are tied to countless different Apple services, each of which saves a copy of the credentials separately from the others. Long story short? I have to enter the password umpteen different times, every 90 days. A litany of authorization panels appear to let me know that, when I least expected it, Messages, iCloud, calendar syncing, iTunes connect, iTunes itself, the Apple Store, Xcode’s ADC integration, etc., etc., all need to be reauthorized. And for many of these services I must carry out this dance on my Mac, iPad, and iPhone. Oh, and my Apple TV.

A couple months ago I got it in mind that I would finally take the plunge and see what AppleCare, Apple’s famously courteous and helpful customer support team, could do for me. I was impressed from the outset by the seriousness with which they took my request, and by the assiduousness of the attention they gave to my problem. I was passed up the ranks of the support team until I was on a first name basis with a very helpful agent out of Austin, TX, who, though she seemed unable to solve the problem, also seemed unwilling to give up until she could. She liaised with various groups within and outside of AppleCare, keeping me posted about the status of this, that, or other approach that may or may not get to the bottom of things. Her colleagues who specialized in AppleID problems offered various suggestions and she diligently came back to me with questions about whether I was a member of this or that program. This went on for a week or two, but it felt invigorating. Even though it was tedious, it felt as though we would end up at a solution. Eventually this relentless, passionate agent would figure out the problem and give me the blessed call to let me know that, at last, everything was going to be OK.

And then she never called me again.

I don’t know what happened to my case. Maybe it’s sitting open in the system, in her queue, collecting dust. Maybe she’s moved on to another job and her tickets are collateral damage. Or maybe she just got tired of trying and one day decided to close it without saying another word.

My 90 day anniversary came up again a couple days ago, and I was inspired to, you’ll never believe this, gripe about it on Twitter. Usually my griping is met by a choir of fellow sufferers who also wish they could eliminate this hex on their Apple ID account. This time was no different, although there was one reply that offered an optimistic take. Rosyna Keller assured me that the problem is well known as an ADC-specific issue:

Sure enough, everybody I’ve ever known who suffered the problem has an ADC account, and most if not all of the afflicted are very long-time members. But still I sighed: I anticipated another weeks-long ordeal possibly ending in me being no better off than I was.

All the same, yesterday I decided to take the initiative to send a note to Apple’s Developer Relations support team. After all I’ve done it would be a shame to live with this problem for yet another 90 days if there are simple steps that could prevent it.

I went to the Contact Us page for the Apple Developer Program, selected “Access Issues” as the subject, and entered the following message:

For years I have been forced to reset my Apple ID ([My AppleID]) password every 90 days. I recently went through an unproductive, several-days-long support interaction with AppleCare that ended in no change. I have recently been encouraged to believe that actually my affiliation with ADC may be the source of the security restriction.

Is it possible for you to lift the password reset requirement on my account? It’s frustrating to have to change every 90 days especially because so many different Apple services, many of which do not share a centralized, common keychain entry, require the password to function at all. Every 90 days is marked by a sudden explosion of password dialogs on my Macs, iPhone, iPads, etc.

My team ID is [My Team ID]. Thank you for any help you can provide,

Daniel Jalkut
Red Sweater Software

That was yesterday. Today, less than 24 hours after I submitted the request, I got a call on my phone from an area code (916) that I recognized as coming from far Northern California (Sacramento and above). I struggled to imagine who could be calling me from that part of the world, but was relieved when I picked up and met my senior advisor from Apple’s Developer Relations support team.

She indicated clearly that she was filing a ticket on my behalf with the technical team, asking them to look for any flag on my account that could cause this. She suggested that probably what will happen is they will find something, eradicate it, and then they will ask her to keep the ticket open for 90 days to ensure that the problem has in fact been addressed. In the mean time, she promises to keep my apprised of any news.

The main difference between this interaction and the previous interaction with AppleCare is that my contact in the developer support team seems to actually recognize this is an issue and seems confident that it can be fixed. I asked her a little more about it and she said it did sound familiar but she hadn’t run into the problem for a long time. She tended to think it has something to do with an old option for password expiration that was available in the past but no longer is. Curiously, she said she had run across the issue a few times suddenly just in the past few days. I wonder… maybe I’m not the only one who got inspired by Rosyna’s tweet.

I’m not 100% confident that my problems with the 90-day Apple ID password expiration are over, but I would definitely go so far as to say I’m cautiously optimistic. If you’ve suffered with this problem and felt there was nothing to be done about it, maybe it’s time to get in touch with developer support and see if there is enough optimism to go around.

Re-signing Code

Automation, Xcode

Given the implied urgency of Apple’s demand that developers provide updated versions of apps with “version 2” code signatures, many people are scrambling to get their build processes updated so that e.g. the apps are built on 10.9 or higher. This is the most natural and attractive technique for ensuring that your Mac apps are signed properly.

However, for a variety of reasons many of us either need to build with older versions of Mac OS X or Xcode. We face a conundrum that can be solved by signing (or more accurately, re-signing) the apps on 10.9, ensuring that the signature is up to snuff even if the code was compiled and the app was assembled with earlier tools.

This is a fairly straight-forward process, but there are some gotchas and you should be aware of what effect running codesign with various flags will have on your finished product. In a nutshell, you want to establish new code signatures on all the binaries in your bundle, but you don’t necessarily want to reset specific entitlements or other metadata that was set on the code by your old-and-busted code signatures.

Felix Schwarz offers a bash script suited to re-signing and further packaging the resulting app into a .pkg file suitable for submission to the Mac App Store. If you’re looking at automating this process, his script may serve as a good starting point!

In my tests I ran into some issues having to do with the fact that some of my apps have custom “designated requirements.” I have ironed out all the kinks yet but it seems to help in this scenario to re-establish all the code signing for the bundle first and then as a final icing on the cake, re-sign the app package with the custom designated requirement.

Take This Code and Sign It

Xcode

Big news from Apple this week that forthcoming releases of Mac OS X 10.9.5 and 10.10 will enforce new policies that will render some 3rd party apps “untrusted” unless they are updated. The long and short of it is that apps using an older version of code signing will not be trusted, and even those using the newer version must forego the use of custom “resource rules,” which allowed developers to exclude certain files in a bundle from consideration as part of the code signature. A file that was thus excluded could be removed or modified without “breaking the seal” and triggering warnings about the code signature.

Jeff Johnson points out a far-reaching implication of this new limitation, which is that developers who bundle frameworks in their apps will need to see to it that the header files are either removed before signing the framework, or left in-tact. Removing the headers after signing will now necessarily lead to a broken seal and thus an untrusted app that Gatekeeper refuses to run.

Jeff’s novel solution involves overriding the default location both for where frameworks install their headers while being built, and for where host apps look for the headers of frameworks they depend upon. This seems like a reasonable solution that many people will benefit from.

Me? I’ve been burned too many times by default code signing behaviors, so I long ago switched to an approach which many will consider too complicated, but which has nonetheless saved my bacon on repeated occasions. The “resource rules” change from Apple wouldn’t have even registered on my radar, because the final code signing of all my bundled frameworks, plugins, XPC services … every darned executable, is controlled by a custom build phase which is run very late in my apps’ build process, right before the final code signing of the overall app that Xcode handles at the very end.

How does this work in practice? Here’s what MarsEdit’s build process looks like from Xcode’s build phase editor:

Screen Shot 2014 08 05 at 2 51 43 PM

You can see that the process of assembling a typical Red Sweater app involves a lot of building up (copying things in), followed by a lot of tearing down, in which I remove framework headers, localizations, etc. These processes are basically fast enough that I don’t mind doing it all programmatically at build time, because it lets me worry less about the pristineness of individual components, and leaves me with with confidence that everything in the final product has been cleaned up. For the Mac App Store build I even have an additional build phase at the end called “Verify Mac App Store Requirements” in which I double check things that have bit me before in App Store submissions, but which Apple doesn’t flag themselves as part of the submission process.

That item at the very bottom is where all the good code signing happens. It’s a somewhat complicated python script that in turn relies upon a library of utility script modules I’ve written for these kinds of things, but the gist of what the “Sign Bundled Frameworks, Apps, Bundles & Tools” build phase does is:

1. Identify the target app being built. In python, you can do this using something like this in a build phase script:

appBundlePath = "%s/%s/" % (os.environ["BUILT_PRODUCTS_DIR"], os.environ["WRAPPER_NAME"])

2. Iterate through the target app bundle, looking for “executable” code. I could hard-code this for every project, but I like the relative safety of knowing that if I add a framework, tool, whatever, it will get caught in this phase. There is also a little gotcha here in that you want to find and sign the deepest items first e.g. so that you sign a helper tool in a framework before the framework that contains it. I have a python module that handles iterating for these items and returns the path to each one in appropriate order.

3. Now the moment of truth: for each item you find, you want to sign it in such a way that you give it your final blessing with all the nuanced code signing flags you care about. My actual code is a little more complicated than this in that I have special cases to avoid using Apple’s timestamp server for debug builds, and some other little tweaks. A common kind of customization you might want to make is to e.g. add arguments to codesign that will cause the preservation of entitlements, so that e.g. an XPC service with its own entitlements will not have those blown away by your re-signing of the app. See “man codesign” for more information about the “-preserve-metadata” option and other flags. But keeping things simple, the gist of signing the code manually from python in a build phase looks like this:

def signAppOrExecutable(thePath):
	signingIdentity = os.environ["CODE_SIGN_IDENTITY"]
	signArgs = ["/usr/bin/codesign",]
	signArgs += ["-f", "-s", signingIdentity, thePath]

	myCall = subprocess.Popen(signArgs, stdout=subprocess.PIPE)
	myResults = myCall.communicate()
	return (myCall.returncode == 0)

Pass the path of every executable tool, plugin, bundle, library, framework, and helper app to this function right before your app is finished building, and all of your custom tweaks, removed header files, adjusted content will be sealed into the final code signature, and you’ll never (ha!) have to think about it again. “Simple,” right?