tl;dr: In late 2019, Apple published an updated macOS Sierra installer which broke the ability to create bootable installation media, failing with an error like /Volumes/XYZ is not a valid volume mount point.

Attempting to use Sierra’s createinstallmedia on my macOS Catalina machine yielded a slightly different set of problems, but with a bit of reverse-engineering, I was able to figure out how to make it work.

If you don’t care for the nitty gritty technical analysis, you can skip right to the instructions below.

technical deep-dive

The oft-suggested workaround, assuming you have an older Mac upon which the Sierra installer can be installed, involves finding and downloading an older copy of Install macOS Sierra.app from a who-knows-how-trustworthy source, running createinstallmedia from within the newer installer app bundle, and then renaming the older installer app bundle out from under createinstallmedia before confirming that you’d like to erase the target disk.

Gross.

With those instructions, if you don’t have an older Mac upon which you can install the Sierra installer (or if it’s not in working order), you’re kind of out of luck.

I neither had an older Mac, nor was I content with downloading a possibly-sketchy older version of the installer from some random place on the internet, so I set my sights on figuring out how to prepare the installation medium from my Catalina machine.

problem #1: missing InstallESD.dmg

After downloading InstallOS.dmg via the Download macOS Sierra link in step 4 of this Apple support document, I mounted the disk image, and attempted to run the installation package, only to be met with this dialog:

Oops. My machine (a 2019 Mac mini) is too new to run Sierra, so the installer package is preventing me from even installing Install macOS Sierra.app.

OK, fine—we’ll extract the contents of the installer package manually:

% pkgutil --expand-full /Volumes/Install\ macOS/InstallOS.pkg ~/Desktop/InstallOS

Note that we use pkgutil’s undocumented --expand-full flag here, because --expand isn’t enough to cause Install macOS Sierra.app to be extracted from the Payload file within the installer package.

Now let’s copy the installer app to /Applications:

% sudo ditto ~/Desktop/InstallOS/InstallOS.pkg/Payload/Install\ macOS\ Sierra.app \
    /Applications/Install\ macOS\ Sierra.app

And attempt to run createinstallmedia (assuming we have a blank flash drive mounted at /Volumes/Untitled):

% sudo /Applications/Install\ macOS\ Sierra.app/Contents/Resources/createinstallmedia \
    --volume /Volumes/Untitled \
    --applicationpath /Applications/Install\ macOS\ Sierra.app

Immediately, we get /Applications/Install macOS Sierra.app does not appear to be a valid OS installer application. Grr.

Using Hopper to disassemble createinstallmedia, I quickly narrowed in on the cause of the does not appear to be a valid OS installer application error message, centered around a failing validation routine called at address 0x1000017a3:

00000001000017a0         mov        rdi, r13
00000001000017a3         call       sub_100001cb2
00000001000017a8         cmp        eax, 0x1
00000001000017ab         je         loc_1000018b7
00000001000017b1         test       eax, eax
00000001000017b3         je         loc_10000198c

If the validation routine at sub_100001cb2 returns 1, we jump to 0x1000018b7 and continue on. If it returns 0, we jump to 0x10000198c, at which point the does not appear to be a valid OS installer application message is printed, and the program exits. If it returns anything other than 0 or 1, we don’t jump anywhere, and execute the next instruction after 0x1000017b3.

sub_100001cb2, as Hopper calls it, isn’t too terribly difficult to read, but rather than regurgitating a wall of x86_64 assembly here, I’ll just explain what it does. It:

• Accepts an NSString * as its only parameter, which is the path to Install macOS Sierra.app that the user specified for the --applicationpath flag to createinstallmedia
• Validates the existence of that path, and that it’s a directory
• Ensures that the bundle identifier of the application begins with com.apple.InstallAssistant
• Looks for SharedSupport/OSInstall.mpkg within the app bundle, and if it can’t find that, falls back to looking for SharedSupport/InstallInfo.plist
• If InstallInfo.plist exists, it then looks up the System Image Info -> URL key, and looks for a disk image named after that value, which is expected to contain OSInstall.mpkg

Here’s our first problem.

InstallInfo.plist looks like this:

% plutil -p /Applications/Install\ macOS\ Sierra.app/Contents/SharedSupport/InstallInfo.plist
{
  "Additional Installers" => [
  ]
  "Additional Wrapped Installers" => [
  ]
  "OS Installer" => "OSInstall.mpkg"
  "System Image Info" => {
    "id" => "com.apple.dmg.InstallESD"
    "sha1" => ""
    "URL" => "InstallESD.dmg"
    "version" => "10.12.6"
  }
}

System Image Info -> URL tells us we’re looking for InstallESD.dmg, and sub_100001cb2 expects that path to be relative to the SharedSupport directory. Let’s see what’s in SharedSupport:

% ls /Applications/Install\ macOS\ Sierra.app/Contents/SharedSupport 
InstallInfo.plist

D’oh! No InstallESD.dmg.

After a bit of head scratching, I realized that, because InstallOS.pkg never ran successfully, its link_package script never ran, which contains this very important line:

/bin/cp "${PACKAGE_PATH}" "${SHARED_SUPPORT_PATH}/InstallESD.dmg"

Easy fix—since we’ve already extracted InstallOS.pkg, we can copy InstallESD.dmg over manually:

cp ~/Desktop/InstallOS/InstallOS.pkg/InstallESD.dmg \
    /Applications/Install\ macOS\ Sierra.app/Contents/SharedSupport

Cool, that’s that out of the way.

problem #2: mismatched bundle version strings

Now, at this point, you might be tempted to run createinstallmedia again.

Don’t do that.

Without fixing one last issue, attempting to run createinstallmedia will cause it to spawn copies of itself ad infinitum until your machine runs out of RAM, or you sudo killall -9 it.

That’s because of one additonal check in our friend sub_100001cb2. The pseudocode looks like this:

loc_100001dc1:
    r14 = 0x0;
    rdx = rax;
    if ([r13 fileExistsAtPath:rdx] != 0x0) {
            rbx = [[r12 infoDictionary] objectForKey:@"CFBundleShortVersionString"];
            r14 = 0x1;
            if ([var_38 isEqualToString:@"com.apple.InstallAssistant.Sierra"] != 0x0) {
                    CMP([rbx isEqualToString:@"12.6.03"], 0x1);
                    r14 = 0x1 - 0xffffffff + CARRY(RFLAGS(cf));
            }
    }
    rax = r14;
    return rax;

r13 is an NSFileManager *, rdx is /Applications/Install macOS Sierra.app/Contents/SharedSupport/InstallESD.dmg, and var_38 is the bundle identifier of Install macOS Sierra.app (com.apple.InstallAssistant.Sierra).

If InstallESD.dmg exists (which it should, now that we’ve copied it into the app bundle), and if the bundle identifier is com.apple.InstallAssistant.Sierra (it is), then we check to see if the CFBundleShortVersionString is 12.6.03. Depending on the result of that comparison, r14 is set, and is then returned in rax.

The Hopper-generated pseudocode for the assignment to r14 looks a little weird—the assembly looks like this:

0000000100001e39         cmp        al, 0x1
0000000100001e3b         mov        r14d, 0x1
0000000100001e41         sbb        r14d, 0xffffffff

My x86_64 assembly-fu was just rusty enough that that didn’t make immediate sense to me, and I didn’t feel like launching createinstallmedia under lldb to debug interactively, so I whipped up a quick test program to help me understand what that code was doing:

int main(int argc, const char * argv[])
{
    @autoreleasepool {
        BOOL result = [@"12.6.03" isEqualToString:@"12.6.03"];
        int32_t var = 0;
        asm (
            "cmpb $0x1, %1\n"
            "movl $0x1, %0\n"
            "sbbl $0xffffffff, %0\n"
            : "=r" (var)
            : "r" (result)
        );
        printf("result: %d; var: %d\n", result, var);
    }
    return 0;
}

That gives us:

result: 1; var: 2

Changing either of the strings in the -isEqualToString: comparison so that they don’t match gives us:

result: 0; var: 1

Interesting—so our validation routine at sub_100001cb2 must be returning 1 or 2 (the former if the strings don’t match, and the latter if they do match). Recall that if sub_100001cb2 returns 0, we get the /Applications/Install macOS Sierra.app does not appear to be a valid OS installer application error.

So let’s see if our Info.plist has the bundle version we’re expecting. Survey says:

% plutil -p /Applications/Install\ macOS\ Sierra.app/Contents/Info.plist \
    | grep CFBundleShortVersionString
  "CFBundleShortVersionString" => "12.6.06"

Aha! So sub_100001cb2 must be returning 1, which results in us jumping to loc_1000018b7, and doing this:

loc_1000018b7:
    rax = [NSBundle bundleWithPath:r13];
    rax = [rax pathForResource:@"createinstallmedia" ofType:0x0];
    var_40 = rax;
    if (rax != 0x0) {
            r14 = var_38 - 0x1;
            var_30 = [NSMutableArray arrayWithCapacity:sign_extend_64(r14)];
            if (var_38 >= 0x2) {
                    rbx = rbx + 0x8;
                    do {
                            [var_30 addObject:[NSString stringWithUTF8String:*rbx]];
                            rbx = rbx + 0x8;
                            r14 = r14 - 0x1;
                    } while (r14 != 0x0);
            }
            r14 = [NSTask launchedTaskWithLaunchPath:var_40 arguments:var_30];
            [r14 waitUntilExit];
            exit([r14 terminationStatus]);
    }
    else {
            fprintf(**___stderrp, "%s does not appear to be a valid OS installer application.\n", [r13 UTF8String]);
            exit(0xfffffffffffffffd);
    }
    return;

Meaning, this copy of createinstallmedia will spawn a copy of itself as a child process with identical arguments, and wait for the child to exit. Since it’s been given the same arguments as its parent, the child process executes in exactly the same way, and ends up reaching this code, where it too spawns a copy of itself, and waits for that process to exit. And on and on… 😐

Thankfully, this is also an easy fix: we can just modify Install macOS Sierra.app/Contents/Info.plist to have the “correct” bundle version string:

% sed -i '' -e 's/12\.6\.06/12.6.03/' \
    /Applications/Install\ macOS\ Sierra.app/Contents/Info.plist

Verify that did the trick:

% plutil -p /Applications/Install\ macOS\ Sierra.app/Contents/Info.plist \
    | grep CFBundleShortVersionString
  "CFBundleShortVersionString" => "12.6.03"

Brilliant.

Moment of truth—let’s try running createinstallmedia again:

% sudo /Applications/Install\ macOS\ Sierra.app/Contents/Resources/createinstallmedia \
    --volume /Volumes/Untitled \
    --applicationpath /Applications/Install\ macOS\ Sierra.app
Ready to start.
To continue we need to erase the disk at /Volumes/Untitled.
If you wish to continue type (Y) then press return:

Yahtzee! That seems to have done the trick.

just give me the instructions, dammit

Note that I performed these steps on a machine running macOS Catalina (10.15.6). I don’t see any reason why these steps wouldn’t work on older versions of macOS, but, y’know, YMMV.

• Download the macOS Sierra InstallOS.dmg from step 4 of this Apple support document by clicking the Download macOS Sierra link
• Mount the newly-downloaded InstallOS.dmg disk image by double-clicking it
• Extract the contents of the installer package to your desktop:

pkgutil --expand-full /Volumes/Install\ macOS/InstallOS.pkg \
    ~/Desktop/InstallOS

• Copy Install macOS Sierra.app to your /Applications folder:

sudo ditto ~/Desktop/InstallOS/InstallOS.pkg/Payload/Install\ macOS\ Sierra.app \
    /Applications/Install\ macOS\ Sierra.app

• Copy InstallESD.dmg to the SharedSupport directory within the installer app bundle:

cp ~/Desktop/InstallOS/InstallOS.pkg/InstallESD.dmg \
    /Applications/Install\ macOS\ Sierra.app/Contents/SharedSupport

• Fix the bundle version string in Install macOS Sierra.app’s Info.plist:

sed -i '' -e 's/12\.6\.06/12.6.03/' \
    /Applications/Install\ macOS\ Sierra.app/Contents/Info.plist

• Finally, run createinstallmedia:

sudo /Applications/Install\ macOS\ Sierra.app/Contents/Resources/createinstallmedia \
    --volume /Volumes/Untitled \
    --applicationpath /Applications/Install\ macOS\ Sierra.app

The last step assumes you’ve got your target flash drive mounted at /Volumes/Untitled. If necessary, replace that path with wherever your flash drive is mounted. createinstallmedia will format and overwrite that drive, so Type Carefully™.

Look at you! You’ve got the macOS Sierra installer on a bootable flash drive.

I never kept particularly close track of how many books I read in any given year, but I could easily whip through books of a few hundred pages in length in just a couple of days.

Not so anymore—the last time I remember sitting down and finishing a book was years ago.

Sure, I’ve made plenty of attempts since then, but I always seem to indulge in some distraction or another that leads me to put the book down. Then some number of months go by, and when I finally remember the book I’ve left unfinished, I’ve forgotten everything I’d read up to that point.

Boom. Instantly less motivated to pick the book back up. And starting from the beginning feels like more effort than I’m willing to expend.

I feel similarly about writing.

I often think that if I wasn’t a software engineer, I’d be a writer (or maybe a musician if the stars were to align). But as with my reading muscle, my writing muscle has severely atrophied. That’s a bummer both creatively and professionally—especially with the explosion in remote work in the wake of the COVID-19 pandemic. It’s never been more important to be a great writer and communicator.

For me, writing has always required a lot of focus and willpower, because I’m a bit of a perfectionist (OK…I’m a raging perfectionist). I rarely let myself get the words down on the page before I start editing, which slows me down considerably. Any of my friends that have witnessed me obsess for four hours over a single, simple email know what I’m talking about.

Now, I find it so difficult to concentrate on reading and writing anything meaningful and long-form that I just don’t do it.

In my case, there are at least a few factors at play, not least of which is the anxiety-inducing pandemic we’re all living through at present, or the fact that I’m still recovering from the mental and physical stress caused by the incredibly toxic work environment of my previous job. I think the more damning thing, though, is the culture of attention and outrage that we as a species have so successfully cultivated in recent years.

Some time ago, I managed to excise Twitter and Facebook from my daily routine, and I’m much happier for it; you should give it a try. But the habits I formed stayed with me, and the empty space left by social media was quickly filled by Hacker News, CNN, and my pile of RSS feeds (yes, RSS feeds—RIP Google Reader, long live Feedbin). Even as I write this, I feel a near-constant anxiety and compulsive need to jump over to my web browser and check those sites, just in case there’s anything new to see, which is awfully draining, to put it lightly. And every time my phone dings to tell me about a new message, I feel a Pavlovian need to pick it up and respond immediately (five times in the last few minutes).

I had to put the fucking thing in Do Not Disturb.

I might leave it that way permanently.

If you’re still reading this, maybe you’re suffering a similar fate: drowning in distractions, having difficulty composing your thoughts, struggling to read anything longer than 280 characters, etc. In other words: focus atrophy.

I don’t have any quick fixes to offer—and, accordingly, this blog post isn’t titled “Regain your focus and conquer inane distractions with this one weird trick!” However, I’m writing this in the hope that it’ll remind me what it feels like to focus on something creative and productive; to help me get back on the horse, so to speak.

Try turning your phone off or putting it in Do Not Disturb, and sit down for some focused reading. Start that blog you’ve always wanted to start, or simply write in a private journal.

Maybe that’ll set you in the right direction, too.

Stay safe out there, folks.

I’m thrilled to announce that, effective March 9th, I’ll be joining EVA Automation, where I’ll be working on exciting as-yet-unannounced things. (Leaving Apple doesn’t mean I get to eschew secrecy, apparently. 😉)

Words can’t easily describe how difficult it was to leave. After two summer internships and a two-and-a-half-year full-time stint split between the Mac and iOS Safari teams, Apple (and Safari) felt like home.

I can’t deny, though, that I felt restrained in that role. I’ve always had dreams of making games (among other things), and I couldn’t do that while bound by a policy barring me from developing apps on my own time. Leaving Apple gives me that freedom once again.

Of the many things I’ll miss, my brilliant teammates take the cake. I learned more from them, every single day, than I ever could have hoped to learn in school.

Maybe I’ll regret leaving, but I don’t think so.

I feel like this journey has only just begun.