Trying to make a Virtual Machine from Apple’s recent DMG releases of Mac OS X

Scroll down to “Update and Solution” to see how to get this to work.

Apple recently released new installers for Mac OS X/OS X/mac OS to deal with expired certificates:

If an installer says it can’t be verified or was signed with a certificate that has expired – Apple Support

Three of the six are links to the Mac App Store:

The other three are URLs to download DMGs:

Today I tried (and failed) to create a new Virtual Machine in either Parallels or VMware Fusion using one of these DMGs, specifically, the El Capitan one.

I will explain what I did, and where I got stuck, in the hopes that someone else might figure out what I did wrong and point me in the right direction.

Download the DMG

Apple has created three DMGs for Yosemite, El Capitan, and Sierra, but couldn’t be bothered to give them useful names, so Yosemite and El Capitan are called ‘InstallMacOSX.dmg’ and Sierra is ‘InstallOS.dmg’.

Likewise the DMGs aren’t named usefully when you mount them either, so make sure you name the DMGs well when you download them to avoid confusion. Here’s how to download it and rename it at the same time

curl --fail --location --continue-at - --output "$HOME/Downloads/InstallElCapitan.dmg" \

Mount the DMG

Open the ‘~/Downloads/InstallElCapitan.dmg’

That will leave you with

“/Volumes/Install OS X/InstallMacOSX.pkg”

Extract the App

Don’t try to install from that .pkg file, it probably won’t work unless the Mac you’re using is capable of running El Capitan:

Instead, open it with Suspicious Package which will let you examine the contents of the .pkg file, as shown here:

Note the area in the red box. Obviously that’s not the full installer, despite the .dmg being over 6 GB. But let’s export it anyway:

Save it to /Applications/ (or wherever you prefer, but that’s where I’ll assume it is for the rest of these instructions).

Don’t eject “/Volumes/Install OS X/InstallMacOSX.pkg” yet, we still need to get the actual .dmg from it.

Get the other DMG

Download The Archive Browser if you don’t already have it (it’s free!) and use it to open “/Volumes/Install OS X/InstallMacOSX.pkg”.

It will look like this:

Click on the triangle to the left of “InstallMaxOSX.pkg” to reveal its contents, and select the “InstallESD.dmg” file from it.

Once it is selected, choose “Extract Selected” from the bottom-left. Save it to ~/Downloads/ (it won’t be staying there long).

Ok, this part could be confusing…

When The Archive Browser exports the file, it will not just export the “InstallESD.dmg” file. First it creates a folder “InstallMacOSX” and then it created “InstallMacOSX.pkg” inside that folder, and the “InstallESD.dmg” file is put inside the .pkg… but you can’t see it, because the .pkg file won’t let you open it.

That’s OK, because we’re going to use to move the file into place anyway.

First we need to create a directory inside the ‘Install OS X El’ which we previously saved to /Applications/. We’re going to use the same folder for two commands and we want to make sure we get it exactly right both times, so we’ll make it a variable:

DIR='/Applications/Install OS X El'

Then use the variable with mkdir to create the folder:

mkdir -p "$DIR"

and then we need to move the “InstallESD.dmg” file into that folder

mv -vn "$HOME/Downloads/InstallMacOSX/InstallMacOSX.pkg/InstallESD.dmg" "$DIR"

Note: you probably want to trash the ‘~/Downloads/InstallMacOSX/InstallMacOSX.pkg’ (and its parent folder) now that it is empty, to avoid confusion later

mv -vn "$HOME/Downloads/InstallMacOSX/" "$HOME/.Trash/"

Now if you look at the ‘Install OS X El’ in the Finder, it should show itself as 6.21 GB:

open -R  '/Applications/Install OS X El'

So close, and yet…

VMWare was willing to start trying to make a virtual machine using the app, but it failed when it came to the actual installation part:

I don’t know what to try next. Parallels would not use either the ‘Install OS X El’ or the ‘InstallESD.dmg’ to try to create a new virtual machine.

Update and Solution

I posted a question on the VMware Fusion support forum asking how to do this, and someone came up with a very clever solution, which I will replicate here in case others are interested. The idea is simple, but I never would have thought of it.

  1. Create a virtual machine of any version of macOS, even the current version that you are using on your Mac.

  2. Inside the VM, download the .dmg (see below) and mount it.

  3. Launch the .pkg inside the .dmg.

  4. The .pkg seems to understand that it is inside a VM, and will install the app, which it would not do outside of the VM. Note that the says that it will only take a few megabytes, but that is incorrect.

  5. Find the “Install OS X El” (or whatever the app name is) in the /Applications/ folder inside the VM. It should be over 6 GB in size.

  6. Copy the “Install….app” from the VM out to your actual Mac.

  7. Create a new VM using the “Install….app” from the /Applications/ folder on your Mac.

Step #4 is the part that I never would have guessed. The .pkg would not install the app outside of a VM, but will install it inside of a VM.

This worked perfectly with the El Capitan .dmg file, and I’m currently doing the same with Yosemite and Sierra. Then I’ll try the older versions of Mac OS X from old installers that I have from before they disappeared from Apple’s servers.

Update 2

Turns out that Rich Trouton wrote about this technique back in early 2017:

Downloading older OS installers on incompatible hardware using VMs | Der Flounder

But I wasn’t working with VMs at the time, so I must not not stored that in my long-term memory.

Update 3

I had saved the older installers for Lion, Mountain Lion, and Mavericks, which are no longer available for download.

Each of them still installed as a VM. Apparently they were not signed with the certificates that expired.

Older versions of Mac OS X (10.6.8 and before) are not available to virtualize.

David Sparks released a new Field Guide for Shortcuts. You should absolutely buy it.

I’m on the record as having been completely wrong about Shortcuts (neé Workflow) for iOS. I was convinced that Apple would never allow it as a third-party app. Even after it was initially approved, I was sure that one day the Workflow team would release an update, and someone on Apple’s review team would realize that this app never should have been approved. So I pretty much ignored it.

When the app was acquired by Apple, I was equally convinced that Apple would kill it, cripple it, abandon it, or otherwise ruin it. “Obviously” Apple just wanted the developers, but the app was unlike anything Apple had done with iOS before, so why would anyone believe that it had any kind of future at all?

There are rare occasions in life when you are very happy to be very wrong.

However, the practical implication of my assurance that Workflow had no future was that I never learned how to use it. When Shortcuts came out as an official Apple app, I felt completely lost. Fortunately, David Sparks of Mac Power Users fame published a “Siri Shortcuts Field Guide” — a video course which demonstrated how to go from knowing nothing about Shortcuts to learning some advanced techniques. I jumped in with both feet. I downloaded all of the videos and watched them on my Apple TV with my iPad in my lap. At the end of the videos, I felt very comfortable with Shortcuts, and ended up making over 150 Shortcuts. Some of them are fairly simple, but some of them are fairly complex (I mean, they aren’t Federico complex but they were respectable.)

Just when I got good at the game, it changed.

When iOS 13 was announced, Apple also announced significant changes to Shortcuts. First of all, it would no longer be a separate app that you have to download, it would be a part of the OS. As a result, Shortcuts would be gaining great new functionality — Hurray! — and also be changing drastically Hurra — wait, what?

I was actually frustrated by this announcement. I’m not proud of that. I think it’s a function of getting older and being less mentally flexible, which isn’t something I’m happy to realize or admit. There was a time when any new software release for send me deep-diving into every corner, nook, and cranny exploring and looking for new things. (I used to go through each pane of System Preferences looking for new things when macOS updated.)

To be fair, I tried to keep up. I installed the iOS 13 public betas with the full intention of trying to learn the new ways of doing things. But as you’ve probably heard, this year the betas for iOS have been rough. When I started to hear about iCloud problems, I immediately backed off the betas and stopped using my iPhone and iPad for all but the bare necessities — and many of those didn’t even work!

Eventually I did look at Shortcuts, but so much had changed that it felt strange instead of familiar. I tried a few things but when something didn’t work, I was left wondering I was doing it wrong, or if I was finding bugs in the system. Overall, it was just frustrating.

When I heard David say that he was updating his Shortcuts Field Guide, I was relieved.

When I heard him say that he was basically having to re-do the entire guide and planned on releasing it as a new, separate guide, I nodded in complete understanding. Even some of the basics have changed. It’s almost like the third time that the app has been a “Version 1.0” — once as “Workflow”, once after being acquired by Apple and renamed “Shortcuts”, and now again as “Shortcuts integrated with iOS”.

The good news is that I think this third iteration is likely to stick around longer than the previous two. I have no actual insight into Apple, Inc., but I wonder if perhaps Shortcuts had to go through these transitions before being fully “adopted” by Apple as one of its own. Since it is now part of iOS, I think the transition is complete.

The Challenge and the Opportunity of Shortcuts

The challenge with Shortcuts being on its third major revision is that there is a lot of outdated information out there. Trying to find current and accurate information is challenging. Some of the old ways no longer work, some of them have newer and easier alternatives, and some of it was simply not possible before. If you simply head to your favorite search engine to find help, you could end up frustrated and confused. That will improve over time, but right now, it’s a significant hurdle.

That doesn’t mean this is a bad time to get into Shortcuts. In fact, I would say just the opposite. If you have not spent time with Shortcuts before, or if you have but realize that a lot has changed, then you know the opportunity is just waiting for you to create ways to make life simpler for yourself through the automation possibilities Shortcuts offers.

If you want to make your own Shortcuts, and — perhaps more importantly– if you want to understand the way that Shortcuts works on a conceptual level, then what you want is someone who can walk you through the process. Ideally, you would like to be able to watch as someone who knows what they are doing goes through the steps of building both simple and more complicated shortcuts.

“Shortcuts Field Guide, iOS13 Edition” is David Sparks’ instructional tour, which begins with the “whys and hows” of the foundational pieces, then works up to the intermediate level of specific features and functions, and finally opens the throttle to show you the new advanced triggers and automation power which were never possible before. All along the way, you’ll get to watch how he works, and as he works he explains the choices that he makes, and why. This is the guide that I wanted and needed to get me ready for the next chapter of Shortcuts on the iPhone and iPad.

David combines two special abilities here: first, an extensive knowledge of Shortcuts, and second, the ability and the experience of a teacher.

Being able to do something is one skill; being able to teach someone else to do it is another. In college, I had the misfortune of having a few professors who could no longer effectively teach introductory courses. They could no longer remember what it was like to be a true beginner. David has been doing these video Field Guides for awhile now, and each one has increased his ability to not just describe or show, but to teach, and he does so with the beginner in mind.

If you start with no knowledge, but have a desire to learn, David’s inviting enthusiasm will be all you need to get started, and at the end you will have learned enough to feel confident in your abilities to go forward to build your own Shortcuts. The name “Field Guide” is a spot-on description of what you’re going to get: someone to walk with you through the process of learning how to use this tool in real-life situations.

(If you have used Shortcuts before, you will appreciate that David also includes some examples of how he has updated some of his Shortcuts to take advantage of the new features and functionality now available.)

There are 6+ hours of videos here, but if you’re like me, it may take you longer than that to finish the course, because I kept pausing the videos to create new shortcuts based on things I had learned. David also includes more than 80 shortcuts which he uses in the videos. They range from a relatively simple “record dictation and save text to an Apple note” to a crazy cool “Link-O-Rama” and a complete “Morning Report” including calendar items and weather conditions. Automation does not need to be incredibly complex in order to be valuable. There is great value in creating a “simple” automation to make a common task simpler and less error-prone, or to eliminate a daily friction point that you might not have even realized was there until you saw a way to eliminate it.

I have no doubt that I will revisit this course in a few weeks or months to see what it might spark in me tomorrow that is different than today, but I have already hugely benefitted from the time I spent watching these videos. Oh, and don’t think that you need to set aside 6 consecutive hours. Most of the lessons are under 10 minutes each, so you can watch a few in separate sittings if you want or need to break it up into smaller chunks.


Don’t tell David, but he has vastly underpriced this Field Guide. My son takes voice and guitar lessons. Each one-hour lesson costs more than this Field Guide.

Imagine that you happened to be friends with David in real life, and you asked him to teach you how to use Shortcuts. How much time would you reasonably expect him to spend with you? Maybe an hour or two, at most?

And because you aren’t a terrible person, you’d want to do something nice for him in appreciation of his time. Maybe you’d offer to take him out to eat (somewhere nice, or at least somewhere without a drive-thru window). Or maybe you’d send him an Amazon or Apple Gift Card. $50 would seem reasonable to me.

Now imagine that he spent six hours with you. And he recorded the conversation so you could go back and rewatch it whenever you needed, with chapter markers so you can jump right to the point you want. And he also made several combo videos so you could download them and watch them anywhere, anytime, in any app you choose (no DRM or any of that nonsense), even if you don’t have an Internet connection.

If you paid him the US minimum wage of $7.25/hour, it would be over $40. (You would also be a terrible friend, because who would pay someone with David’s experience and expertise minimum wage?!?. The kid down the street probably gets twice that for mowing lawns.)

What I’m saying is that there is no way that $29 is a reasonable price because it’s way too low. But David has it priced at $29 anyway.

And if you act fast you might even find a $5 coupon, which makes it only $24, which almost seems like stealing. I pay almost that much for my regular order at Five Guys.

If you bought David’s previous Shortcuts Field Guide, this is a separate purchase, and if anyone complains about this I will campaign to have them thrown off the Internet. So much has changed that there was no way he could have just updated the old course. If you bought the old course and want the new one, it’s most likely because you know how much has changed. Did any of us expect last year that Shortcuts would change so much this year? Of course not. But it did.

This was a huge undertaking, and for it to be ready when iOS 13 launches took a lot of work on David’s part. There is an even bigger discount for those of us who bought the previous version, which is a fair and generous move on David’s behalf. Everything I said above about the cost of this year’s course was true for last year’s course as well, so even if we paid full-price for both, we’d still be ahead. So let’s not be greedy, but rather be grateful that not only is Shortcuts not dead but its future looks quite bright indeed. Which means that your investment today is likely to be useful for a long time to come.

Look, just buy it.

If you’re one of the tens of people who will read this post, chances are high that you like nerdy Mac/iOS stuff. This course is absolutely worth your time and money. Go get it.

Yes. I moved my blog. Again.

I think I’ve tried all of the various platforms now. Of all of them, I wanted to like Squarespace the most, because it seemed like the coolest one, although that could be because I listen to a lot of podcasts. But Squarespace is expensive, and their iOS apps are terrible. I once wrote a post in Markdown on the website and then couldn’t edit it in the iOS app because it was a "complex document" or some nonsense like that.

WordPress has always seemed like the best choice, except that I didn’t want to do it on a cheap, shared host like I had done it before (cough Dreamhost cough) which was terrible (although that was a number of years ago now). I tried Tumblr. I tried Micro.Blog. I tried just about everything. I even tried hosting my own static site. A few times.

But WordPress is everywhere, including on iOS with Shortcuts, and (perhaps especially) on the Mac with MarsEdit. I’ve always liked MarsEdit, and I’ve owned a license for it for as long as I can remember, but most of the various sites that I’ve tried didn’t work with it.

Why did I wait this long to go back to WordPress?

Well, to be honest, I thought WordPress on was going to cost me like $15-20/month, which was more than I wanted to spend. But when I went to sign up, not only did I find that it was much cheaper, but with the promo code PRICINGSAVE20_785F (valid through August 31st, 2019), my account will only cost about $6/month for 24 months.

What is even better (for you, dear reader, if in fact you actually exist) is that 24 months is a long time compared to how long I usually go before I move my site. So it will be here for at least 24 months, and hopefully by that time I will have gotten the urge to stray out of my system.

I’m going to start moving over old posts from my former Micro.Blog site soon.

Who knows, maybe I’ll even stop breaking my own URLs at some point!