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Having troubles installing older versions of OSX on external drive

S

solinari6

macrumors regular
Original poster
Aug 13, 2008
101
16
I've run into a problem where I have a 2020 MacBook Pro, that has been updated to Monterey.

I've got to run Xcode 10.1 to upgrade an old swift project. You can't run Xcode 10.1 on Monterery though. So my plan was to get an external drive, and install an older version of the operating system on that, and then just boot to that when I need it.

Problems though!

Initially I wanted to install High Sierra, the links I found say it should be available to download on the App Store. But it's not there for me, possibly because my Mac is too new to run that. Ok, fine. I found a download link to the full installer for OLD Sierra, and tried to install THAT on my external drive. But the installer won't even run, saying "this version of Mac can't be installed on this computer".

So at this point, I can't figure out how I can get anything older installed on that external drive. Is there supposed to be a way to do this?
 
Is xCode 10.1 supported on Catalina? That would be natively supported on your 2020 MBPro (I'm assuming an Intel MBPro, and not an M1??)
 
DeltaMac said:
Is xCode 10.1 supported on Catalina? That would be natively supported on your 2020 MBPro (I'm assuming an Intel MBPro, and not an M1??)
Click to expand...
From what I can tell the last supported version was Mojave. It won't even install Monterey .... It sounds like some people have gotten it to work on Catalina, though. I guess it's worth trying to install that and see what happens :)
 
solinari6 said:
From what I can tell the last supported version was Mojave. It won't even install Monterey .... It sounds like some people have gotten it to work on Catalina, though. I guess it's worth trying to install that and see what happens :)
Click to expand...
Well crap, I tried to install Catalina, and it says it is too old to install on this Mac :(
 
Is it really a 2020 MBP? Because that would have the M1 CPU and certainly won't support Catalina or Mojave. Check your exact model here

All Apple MacBook Pro Specs (2006-Current): EveryMac.com

Tech specs for all Apple MacBook Pro from 2006 to the latest. Dates sold, processor type, memory info, storage details, configuration options, model identifiers and more.
everymac.com everymac.com

Click on the correct model and scroll down, it will show the oldest supported operating system.
 
Boyd01 said:
Is it really a 2020 MBP? Because that would have the M1 CPU and certainly won't support Catalina or Mojave. Check your exact model here

All Apple MacBook Pro Specs (2006-Current): EveryMac.com

Tech specs for all Apple MacBook Pro from 2006 to the latest. Dates sold, processor type, memory info, storage details, configuration options, model identifiers and more.
everymac.com everymac.com

Click on the correct model and scroll down, it will show the oldest supported operating system.
Click to expand...
Yeah it is, I bought it about a month before they announced the M1 chips :(

It's a 13-inch 2020 running intel i5

Tried to boot into recovery mode to see if it would at least let me install the version of the OS that was on the Mac when it shipped onto the external drive, but the only option I have is install the Monterey Beta (which reminds me that I'm still on the beta ? )
 
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Your 2020 intel MBPro shipped with Catalina, so you should be able to install Catalina from that.
The recovery system would try to Catalina on your existing system, which won't work without erasing your boot volume first.

Best way would be to download the Catalina installer from the App Store.
When that downloads, create a bootable USB from that downloaded installer app, then boot to that bootable installer.
Here's a link to an Apple support article that will guide you through that process.

Create a bootable installer for macOS - Apple Support

You can use a USB flash drive or other secondary volume as a startup disk from which to install the Mac operating system. These steps are primarily for system administrators and other experienced users.
support.apple.com support.apple.com

When you are booted to the Catalina installer, choose your external volume as the destination for the Catalina install.
 
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Boot to a special version of internet recovery:
Command-OPTION-SHIFT-R

This will install the "oldest version" of the OS that can be installed on that Mac.
(I believe this works only with Intel-based Macs)

Does doing it this way offer you Catalina...?
 
Fishrrman said:
Boot to a special version of internet recovery:
Command-OPTION-SHIFT-R

This will install the "oldest version" of the OS that can be installed on that Mac.
(I believe this works only with Intel-based Macs)

Does doing it this way offer you Catalina...?
Click to expand...
Ok, this actually worked! Was able to install Catalina on the external drive. Still having issues actually booting from it though... I hold down the option key while booting, and I get the option to pick which hard drive to boot with. But if I choose the external one, it just restarts the computer and boots into the internal hard drive ?
 
may I ask why you don‘t upgrade the project using the latest version of Xcode? Xcode tends to be quite competent in that regard?
 
Romain_H said:
may I ask why you don‘t upgrade the project using the latest version of Xcode? Xcode tends to be quite competent in that regard?
Click to expand...
The latest version of Xcode CAN'T upgrade the project. When I try to open it, it specifically says I need to load the project in version 10.1, upgrade the project, and THEN I can load it into the latest version of Xcode. Such a friggin hassle ?
 
OP wrote:
"Still having issues actually booting from it though... I hold down the option key while booting, and I get the option to pick which hard drive to boot with. But if I choose the external one, it just restarts the computer and boots into the internal hard drive"

1. Boot to the recovery partition (command-R)
2. When you get there, open "Startup Security"
3. For "Secure boot", choose "No Security".
4. For "External boot", choose "Allow booting from external media"
Quit Startup Security.

Then restart, hold down the option key again to invoke the startup manager.
Try selecting the Catalina drive now.
Does this change anything?

(You only have to change these settings once... assuming it works)
 
Fishrrman said:
OP wrote:
"Still having issues actually booting from it though... I hold down the option key while booting, and I get the option to pick which hard drive to boot with. But if I choose the external one, it just restarts the computer and boots into the internal hard drive"

1. Boot to the recovery partition (command-R)
2. When you get there, open "Startup Security"
3. For "Secure boot", choose "No Security".
4. For "External boot", choose "Allow booting from external media"
Quit Startup Security.

Then restart, hold down the option key again to invoke the startup manager.
Try selecting the Catalina drive now.
Does this change anything?

(You only have to change these settings once... assuming it works)
Click to expand...
Yep, already did that. I'm starting to think there might be something wrong with the external hard drive itself. It seems to "fall asleep" a lot, and disappears from finder until I unplug it and plug it back in
 
so I'm not sure this recovery mode Catalina install actually installed Catalina on that external drive. Since it won't boot from that drive, I booted into Monterey, and just opened the external drive in finder to see what is there.

It doesn't LOOK like an actual install. There's just a folder with the name "macOS Install Data" on it, that's filled with random install things.
 
Sounds like that external has the system files copied to that external, but it never restarted to complete the install.

What brand and model of external drive are you trying to use?
I have an 8TB Seagate Backup Plus external, that I can try to install a bootable system on a partition, but it will not boot. I get that same folder, which won't complete the install. It's a drive that I use for lots of backups and storage, but not one that I can use for a booting drive. But, it was cheap, and I can store lots of "stuff", just can't make it bootable on anything.
 
DeltaMac said:
Sounds like that external has the system files copied to that external, but it never restarted to complete the install.

What brand and model of external drive are you trying to use?
I have an 8TB Seagate Backup Plus external, that I can try to install a bootable system on a partition, but it will not boot. I get that same folder, which won't complete the install. It's a drive that I use for lots of backups and storage, but not one that I can use for a booting drive. But, it was cheap, and I can store lots of "stuff", just can't make it bootable on anything.
Click to expand...
Yeah, I think that's my problem. It's just a Chinese named hard drive I got off amazon ($16 for 320gig). so obviously I wasn't expecting it to last forever, just long enough to do what I needed. LOL

Never could get it to boot, so I just ended up using VMWare, and installing Catalina on that, with the volume installed on the external drive. (man it's slow though). Xcode works there, and hopefully that will work good enough.

Thanks everyone!
 
320GB? That's an odd size - only seen it on hard drives, so a spinning hard drive, not an SSD. That's what I would expect, and will be draggy slow on Catalina, and not a good pick for the APFS format for a Catalina boot drive.
 
DeltaMac said:
320GB? That's an odd size - only seen it on hard drives, so a spinning hard drive, not an SSD. That's what I would expect, and will be draggy slow on Catalina, and not a good pick for the APFS format for a Catalina boot drive.
Click to expand...
Yup, just double checked, and it is 320 :) https://smile.amazon.com/gp/product/B08N6QLB2W/ref=ppx_yo_dt_b_asin_title_o04_s00?ie=UTF8&psc=1

Oh, but get this ...

So when I initially opened my project in Xcode, it said I needed to run Xcode 10.1 to update the swift version. SO I go through all this work to get Catalina installed on the VMWare virtual disk, get Xcode 10.1, open the project and ....

It says I actually need Xcode 8.3 to upgrade from swift 2 -> 3. THEN I need Xcode 10.1 to upgrade from 3 -> latest.
And of course, I can't run Xcode 8.3 on Catalina, so I have to start all over with High Sierra. ?
 
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