In Life, Technology

Painless way to downgrade or backup your Mac OSX from Mountain Lion to High Sierra

In the past week I have been trying to upgrade my MacOSX from Mountain Lion (which no longer exists even as a download) to High Sierra. I am talking 6 leaps in upgrades here, taking advantage of the time I have to get this all done.

What hasn’t helped, are all of these tech-y articles online telling me THE SAME THING over and over again for my issues that I ran across when leaping so far.

This is unusual for my blog to post but I am doing it in the hopes that it helps someone else save 3 days of frustration.


You absolutely need to have two things if you are a Mac user:

  • Time Machine – Free with your MacBook but has limitations
  • Carbon Copy Cloner – I purchased this software and it is fantastic


  • Always keep a current-is copy of your Mac with Carbon Copy Cloner (monthly in my case)
  • Would be easier to ALSO keep a Time Machine backup in parallel but not necessary unless required because you can use CCC and create a Time Machine backup on the fly
  • Have two hard drives dedicated to backing up
  • Back up every month at least if not more often

What does Carbon Copy Cloner do?

It basically creates a bootable Mac, and you can literally use that hard drive clone to plug into ANY Mac, boot off it and WORK ON IT if you wanted, as if you have two Macs.

This may not seem very exciting to you unless you’re also a business owner like me who keeps a separate business laptop and lives in fear of not being able to access years of data and bookkeeping especially come tax time.

At any rate, even if you don’t run a business but your MacBook completely goes black and dies a painful death, you can still use any other Mac you have available to borrow or WHATEVER, boot up from this Carbon Copy Clone drive, and work off it / use it to overwrite the other Mac you have and use it as your new Mac.


This means my laptop could die, and because I have a bootable copy of my entire laptop, I live with zero fear that I could attach the external drive copy to one of my other MacBooks and access all my data and run it as if I had my old laptop.

How to boot up from an external Carbon Copy Cloned drive

To boot up from this external Carbon Copy Cloned drive, go into Settings > Restart > Select the external drive

Works beautifully.

There, you can actually attach a second hard drive now, and use it as a Time Machine backup of your booted Carbon Copy Cloned drive.

Then, you take that Time Machine backup and when you want to reinstall on your actual laptop drive, you select that external hard drive.

Kind of like backing up a copy of a copy.

Issue 1: Downgraded Catalina to High Sierra

Downgrading is a B*tch.

I am not going to Catalina because then my Mac OSX Office Suite 2011 no longer works, and I am not about to buy a 365 Office suite subscription until I am FORCED TO.

I hate paying for subscriptions and will happily fork over money for software I can use for the next 5-8 years, ONCE, rather than pay monthly.

The only thing that saved me, was that I had a Carbon Copy Clone of my MacOSX on my hard drive which is why I am highly recommending you all buy a copy of it.

I booted from the Carbon Copy Clone of my hard drive from when it was still Mavericks using my external harddrive, and then used a second external hard drive to Time Machine clone that drive.

I detached everything, headed into Internet Recovery, and used that Time Machine backup I created to then reinstall my old MacBook before the upgrade.

Issue 2: Couldn’t force a reformat or erase of my MacOSX Catalina

Everything was locked. Couldn’t erase anything, reformat, reinstall any new copy or backup except of Catalina over and over again.

The solution is to boot from your Carbon Copy Cloned bootable drive, then go into Internet recovery, select Disk Utility and delete your Mac OSX operating system there, erasing it completely so you can NOW use your old Time Machine backup on it.

Issue 3: Asked for a recovery key in Catalina and recovery key no longer exists / File Vault is on and I cannot remove it

Check in Settings if you can remove File Vault (you likely have it turned on). It wouldn’t let me in my case.

Each time I tried to boot with regular (not Internet recovery boot), using Command + R, it would ask me for this elusive Recovery Key. I HAVE NO IDEA WHAT IT IS. I still don’t.

Apple says to go into Apple ID and generate a new Recovery Key, but they’ve done away with all of that and moved to Two-password authentication, so this was completely utterly f*cking useless for me.

You cannot get that Recovery Key.

You can’t even remember what that key was, or even that you set it up.

You cannot remove FileVault which determines Recovery Key.

Luckily, I had my .. CCC bootable copy of the laptop back when it was Mavericks, and I just restored it to that (see above).

I know this is missing screenshots and so on, but I hope that info helps you.


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Sherry of Save. Spend. Splurge.

Am my own Sugar Daddy. Am a millionaire at 36 after getting out of $60K of student debt in 18 months, a little over a decade earlier, using I have worked 50% of my career (taking 1-2 year breaks), and quadrupled my income within 2 years of graduating, going from $65K to $260K with an average lifetime savings rate of 50%. I have 11 side incomes that are on track in 2020 to make me $50K - $75K. I could retire today if I wanted, but love my work-life balance as a freelancing consultant in STEM (Science, Technology, Engineering, Math). I am all about balance - between time and money, and also enjoying my money. I also post daily on Instagram @saverspender.

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