Recover all files from a Time Machine backup - what is the correct sequence for Monterey

The Restore from Time Machine Backup option is meant for restoring your entire Mac from a Time Machine backup, including the macOS version, system settings, applications, and user files. This option will erase your internal disk and replace it with the contents of the backup. This is useful if you want to restore your Mac to a previous state, for example, if you have encountered a problem with your current macOS installation or if you have replaced your internal disk with a new one.

However, if you want to upgrade your macOS version to Monterey and keep your existing data, you should not use this option. Instead, you should follow these steps:

• Erase your internal disk using Disk Utility in the Mac OS Recovery environment.
• Install macOS Monterey on your internal disk using the bootable USB installer.
• After the installation is complete, you will be prompted to set up your Mac. During the setup process, you will see a screen that asks if you want to transfer your information to this Mac. Choose the option to transfer from a Mac, Time Machine backup, or startup disk.
• Connect your external drive containing the Time Machine backup and follow the onscreen instructions to select the backup and the items you want to transfer. This may take some time depending on the size of your backup and the speed of your connection.
• After the transfer is complete, you will be able to use your Mac with macOS Monterey and your existing data.

I hope this helps you to understand the difference between the Restore from Time Machine Backup option and the transfer option during the setup process.

gh1852 wrote:

By “manually” I meant boot from USB, opt for Disk Utility, erase the internal disk, then choose Install Mac OS from USB.

I honestly don't know if that's even possible anymore. This is the kind of thing that is documented (Create a bootable installer for macOS - Apple Support) but can be expected to regularly fail. It simply isn't the kind of thing that Apple tests on a regular basis.

You didn't say what operating system was involved. This would likely work in Ventura or earlier. It would likely fail in Sonoma just because Sonoma is constantly in a state of being broken and fixed. This will continue until Sonoma is discontinued next year. Every macOS operating system in recent memory has worked this way. And I know what you are going to say - don't say it. Apple's customers have repeatedly demonstrated that they prefer this method and show their preference in cash, lots of it. Often people complain about the crazy ways that Apple devices work and long for the "good old days". You know the ones, back when Apple was 90 days from bankruptcy. People simply didn't buy back then like they do now. Crazy as it is, Apple's not going back.

Most usage of a bootable flash drive these days are from people installing some alternate operating system like Linux.

When Setup Assistant eventually appears very soon after “Choose your language”, choose the date to restore from, and then restore personal files and settings. I know precisely the date and time the date and time when it all went South, and certainly will NOT use the most recent backup. They have dozens of recent backups that were automatically made in the week preceding it “hit the fan”. That’s all I meant. The intent is to restore the entire system including MacOS to the way it was approximately 11/1/23.

As far as I know it should work. That option is listed here: Restore your Mac - Apple Support

As above, this is not a typical option. It was designed for people buying a new Mac and transferring the latest data over. Older backups are typically individual files or folders, not the entire system.

I had hoped that Restore from Backup would simplify provide some automation. Apparently far from it. I have no idea why Apple even includes the option at this point. But I’m glad that I know now and not when I begin the work.

I'm not sure what automation you are expecting, or what part of the process isn't automated. This is not a quick-n-dirty fix. If it were 11/2 or 11/3, you could do this whole process using a Time Machine local snapshot. That would take maybe 30 seconds. You want to help someone else restore to a month ago? Book a hotel room. You can do it, sure. But there are a month's worth of gotchas waiting for you.

Don't forget the most important part. Take your own external SSD and make a new backup before you start. 😄

gh1852 wrote:

I've provided a bootable USB installer in order to minimize time spent downloading Monterey.

How's that working out for ya? Saved any time yet? 😄

If my friend first chooses Install MacOS Monterey as per the support document, my recollection is that they will immediately go into Setup Assistant after the installation completes.

Yes. That's how it works. Part of the initial installation will include an opportunity to restore from backup. If you want, you can skip that and manually run Migration Assistant later, for a bit of extra complications.

gh1852 wrote:

The issue where my friend lives is that installing MacOS from the recovery partition of the internal hard drive requires 5-½ hours to download, then installation could begin. So am I correct to assume that it’s just a waste of time for them to boot up from the USB and choose the Restore from Time Machine option?

Yes.

If so I’ll just have them do it all manually.

I don't know what you mean by "manually". I don't even know what you are doing at all. A common problem here is the forums is that people follow bad advice on the internet. Invariably, it goes wrong. Then they look for more bad advice and try that. Now their system doesn't boot. They call someone for help and drag that person down into the rabbit hole with them.

It is only at this point that anyone ever posts a question and asks for help. But they aren't asking for help about fixing the actual problem. They ask for help about selecting the proper shovel to deepen their rabbit hole and make it a more comfy place to spend quality time. Then they get angry with our replies, "Get that rope out of my face! Can't you see I'm trying to dig! Where is the famed Apple 'It just works' when my rabbit hole is nowhere near China yet?"

I had hoped that the Restore from Time Machine Backup option had potential for fewer problems when I try to guide them through this over the phone- they’re 250 miles away, and I really don’t want to drive there.

Again, I don't know what the actual problem is or what you are doing. There is a good chance that the entire process will a waste of time.

When it comes to actually erasing a Mac and restoring from backup, it's a pretty simple process. Wipe the hard drive. Reinstall the operating system. Restore from backup.

Yes. The system is most definitely designed for wealthy people who live in major markets with gigabit fibre internet. When someone makes a decision to move out to the boondocks, they have to accept that they are 250 miles away from help if they need it. When their Mac stops working or their heart stops ticking, it's a long drive back into town. It's going to take some time. There are no shortcuts.

But my point is that the erase and restore will work. It is going to restore the computer exactly the point where the last backup was made. Whatever was scrambled on the machine that led these poor people into this mess is going to be restored exactly the same way it was before. Just so you know. All of this work is so you can get back to some point where you can begin to start fixing whatever problem they are having.

If they haven't actually wiped the computer yet, then there might be a shortcut available. Don't do any of that. Identify what the actual problem is and fix that. May I recommend a helpful Apple tech support forum where people just love to provide assistance before everything's gone to **** in a hand basket.