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Al_from_Ottawa 12-13-2017 10:23 AM

Managing Sierra to High Sierra upgrade
Still running Sierra because of compatibility concerns, especially MS Office 2011. Now about to try it. Need advice on best way to do it.

Macbook Pro 2012 with internal 1 TB SSD and available external 500 GB USB3 SSD. Full clone of internal drive will not quite fit in 500 GB. All HFS+ of course. There are some encrypted disk images, but neither drive is encrypted as a whole.

Here's my plan. But I am not sure it will work the way I hope.
- Sandbox clone from internal to external drive.
- Set boot to external then update to High Sierra. If I understand correctly, I will now be running High Sierra but all user file updates will still occur on the internal drive.
- If I want to revert to Sierra, I just have to switch back to booting on the internal drive.
- If I want to stay with High Sierra, I run the OS updater again on the internal drive.
- Either way I don't have to copy anything from the external to the internal drive.
- I would need to clone both drives to fully back up using SD.

1. Does this plan work?

2. What's the best way to handle Time Machine during the transition period? I have a pair of HFS+ encrypted 2TB USB3 drives used in alternation for Time Machine.

3. If I end up running High Sierra I will want to migrate to APFS. First step is probably to clone to an encrypted APFS drive with SD. Then what?

dnanian 12-13-2017 10:29 AM

A Sandbox should work (use "Shared users"), but please ensure you have a backup of your real drive before you do this, in case you have any issues.

I honestly don't know what Time Machine is going to do. It may delete your old backups if you boot from some other drive. I'd probably leave them completely disconnected while you check compatibility.

Not sure what "then what" you're looking for in #3...

Al_from_Ottawa 12-13-2017 01:29 PM

Thanks for your usual quick response.

1. The initial migration: Glad that my plan sounds feasible. I assume that by specifying shared users I will get all users of the MacBook transferred.

2. If I end up on High Sierra, I will want to migrate to APFS. As far as I know, installing High Sierra leaves my boot drive on HFS+. So here is a very tentative plan:
- Using SD, clone the internal HFS+ drive to a freshly formatted APFS external volume. If I understand correctly, you will copy the recovery partition as well if I do that.
- Boot from that clone, and format my internal SSD to APFS. Clone back to the internal drive using SD. I hope that will give me an APFS MacBook with recovery capability.
- Reformat one of my Time Machine drives to APFS. Clone the other Time Machine drive to it using SD. (That will take about 36 hours). Use it for time machine.
- Reformat the other Time Machine drive to APFS and clone to it from the active Time Machine drive. During each of the two TM cloning exercises I will disable Time Machine backups so that the source is stable.

I hope that will end up with all my drives on APFS, and most of my Time Machine file history preserved.Maybe not as much history as I would like, because Time Machine is picky about cloned drives, and may recopy a lot of files that don't need to be updated and in the process it may fill the drives (currently each about 500 GB free out of 2 TB).

dnanian 12-13-2017 01:35 PM

1. Shared, not transferred.
2. If you're not booting from an SSD, you shouldn't use APFS as your regular boot drive. If you upgrade the internal, it should convert for you, if it's an SSD.

Also, Time Machine will not work on APFS. Do not format a Time Machine drive with APFS.

Al_from_Ottawa 12-14-2017 08:00 PM

Thanks for the warning about Time Machine drives.

1. Why Shared Users not Shared Users and Applications? My main reason for using a sandbox is to verify compatibility of applications. So what's wrong with leaving the applications I want to test on the internal drive? Should make it quicker to clone, with no obvious downside. Or will strange things happen if I update low level applications such as 1Password while running the sandbox? Their updaters could detect OS version and do different things, so that if I reboot into Sierra on the internal drive things won't work?

2. You say the High Sierra installer will update an internal SSD to APFS. What will it do with an SSD sandbox external boot drive? Not that it is really critical, because if I do switch permanently to High Sierra, I will be running the installer again on my internal drive and at that point I will get switched to APFS.

dnanian 12-14-2017 08:46 PM

1. I'm trying to isolate things more to improve your chance of not having to restore.

2. It'll probably upgrade it to APFS.

Al_from_Ottawa 12-15-2017 01:38 PM

Thanks. I'll try it that way and report the results in a week or two.

Al_from_Ottawa 12-22-2017 07:17 PM

Progress Report - Eventual Success
Progress report on using Sandbox to test High Sierra.

The Good

- With SSD at both ends, making the Sandbox was quick (under 50 GB to copy)
- I was able to verify that all my important apps work fine in High Sierra, including especially MS Office 2011, which is not officially supported there.
- The whole process was really simple and slick.

The Bad
- When running the sandbox, I could not connect to my AirPrint compatible laser printer.
- When I rebooted on the internal drive, which was of course still running Sierra, the reboot and setup took a very long time. Then several pop up dialogs kept asking me to enter my keychain password to unlock Local Items. The correct password was rejected (though it worked fine to unlock the Login and System keychains). Restarts (which took a normal length of time) did not help. Eventually I discovered that the keychain database had been corrupted (though there were no system messages to that effect). Fortunately I had a Time Machine backup taken immediately before I created the sandbox. Restoring the whole keychains folder from it eliminated the problem. The corruption may have happened during the setup process when I returned to Sierra, since there was no evidence of it when running the sandbox.

Once I had fixed the keychains, I updated the internal drive to High Sierra. That went smoothly, and it has run well since. Printer works normally, so my problems were caused by the sandbox not by High Sierra.

So thanks for the Sandbox concept. Possibly some minor tweaks to the scripts might make it more fully transparent.

dnanian 12-22-2017 09:03 PM

That sounds like High Sierra converted your Keychains to a new format. Since the keychain is local (in your account), it is something we cannot isolate. That's why I do say you should have a real backup as well.

No idea why your printer wouldn't work.

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