The Last Word on OS Upgrades

Dr. Mac’s Rants & Raves
Episode #254

I didn’t intend to write about OS upgrades again this year. But, two things that happened last week forced me to reconsider.

The first was an email from a reader that said:

Should have stayed away from macOS High Sierra. Now my MacBook Pro will not let me login. Have tried everything to fix the problem. Looks like I will be going to the local Apple dealer to get it fixed. Wish I had never tried this update. It won’t even let me re-install macOS.

I devoted a whole column to things you should do before you consider any OS upgrade (see Dr. Mac for Sept. 28, 2017). So, while I sympathized with this person, I didn’t feel obliged to revisit the subject.

Even A Tech Reviewer Struggles…

Then, before I wrote this column, the second thing happened. I read an article by Jim Rossman in the Austin American Statesman entitled, “Even a Tech Reviewer Struggles with Upgrading a MacBook Pro.” In it, he recounts how he tried unsuccessfully to upgrade his MacBook Pro from macOS Sierra (v10.12) to macOS High Sierra (v10.13).

When even tech reviewers have issues with an OS upgrade, you should probably pay attention.
When even tech reviewers have issues with an OS upgrade, you might want to pay attention if you have not upgraded to High Sierra yet.

I don’t know Jim Rossman personally, but I’ve read his work for years and know he covers a lot of the same ground in his columns as I do in mine. In other words, he’s an experienced tech writer, quite familiar with the potential pitfalls and perils that come along with upgrading an operating system.

Still, something went wrong during his High Sierra upgrade. He said, “all I got was a gray circle with a line through it” and a system that, “wouldn’t do anything at all.”

He goes on to say he didn’t follow his own advice about frequent backups, so his most-recent backup was a week old. After using target disk mode to back up files he’d created in the last week to his wife’s Mac, he then restored his MacBook Pro from the week-old Time Machine backup.

Here’s the important part: Restoring from his most-recent Time Machine backup took about 5 hours.

Think about that. Even if you’ve done every single thing I recommend before you upgrade—backing up, backing up again, researching application compatibility at, and searching the Internet for problems others are experiencing—you could still encounter an issue that could leave you Mac-less for 5 hours or more.

The Bottom Line

My point is that when you upgrade macOS (or any OS, for that matter), your device could become inoperable for hours or days, regardless of how well-prepared you are.

I suspect incidents like this are rare these days, but, as the email from my reader and Mr. Rossman’s column make clear, it can and does still happen. So, before you upgrade macOS again, consider whether you can afford to be without your Mac for hours or days.

11 thoughts on “The Last Word on OS Upgrades

  • Hey y’all… Thanks for all the comments and insights! I don’t have anything to add, but I wanted to say that feedback rocks and I read each and every comment… even if I’ve got nothing more to add.


  • High Sierra was primarily for the change in storage device file format from HFS+ to APFS. For that reason and for my general rule to never upgrade to a new OS until at least 10.x.2, I have not yet upgraded. This is a behind the scenes major upgrade, so I am not surprised at the problems described here.

  • Hmmm I have hemming and hawing about moving my early 2013 MB Pro to High Sierra, and have yet to see a clear reason to do so. Everything is working smoothly at the moment. I have the time, the TM backups, a bootable clone. Yet I’m going to hold off for awhile yet, which is odd as a power user and typically, an early adopter.

    It’s a strange place to be in after over 30 years of always having the latest Apple hardware and software, to not be upgrading either on the leading edge of their cycles. It’s a bit troubling that I not only don’t find anything compelling about the newer offerings of either, but actually find the previous iterations working more suitably. But probably that’s just me.

    But thanks for this article and the comments, if I needed any encouragement to delay the upgrade, this is it.

    1. I’m with you also. I’ve been thinking about it on my MBP 2012, but have put it off also. I’ve been an Apple user since 1979 and USUALLY always upgrade about 3 days after a release to check for other’s problems.
      As always, Bob LeVitus gives great advice. While I usually leave my Macs running, so my backups are done daily, I also use SuperDuper to clone all my Macs every couple of months just to be safe. And always before any major updates.
      Have a great holiday everyone.

      Bob M

  • I have to add my voice to the choir. All of my software is up to date, and though High Sierra is a solid update to the OS, my other tools were incompatible to the point of my not being able to do my work on it. I had to downgrade. I had the backups, but it still took me awhile to rebuild libraries etc. that are not included in a migration. This is the sloppiest I have seen Apple in a very, very long time (think Sculley). iOS 11 is not the subject of this article, but there have been issues there as well. I would reccomend that pro users wait until they are sure their software will function properly.

  • Having experienced the ominous and unresolvable gray circle with a line through it, I can sympathize. It was not an upgrade issue for me though. It happens when making a clone of my USB3 capable MacBook Pro (2012). It turns out that one can’t boot from a clone created with USB3 using a USB3 cable. I had to resort to a FireWire 800 cable to boot. Problem solved though I still don’t understand why this happens. Where this long preamble is leading is the need to have a bootable clone before doing an OS upgrade. This way one can restore relatively easily if need be and, more importantly, one can boot from the clone and do real work. Restoration can take place later when it’s convenient.

    1. I confess I don’t fully understand the issue with booting from a clone via USB3 and having to use a FW800 cable. Are you saying that if you have a machine without FW one will be unable to boot to their external clone over USB3? This is my own usage scenario so I am slightly concerned to hear this.

      1. This appears to be an issue only with pre-2013 machines. For example, the same thing happens on a MacMini 2012; however, on a 2013 MB Pro with Retina display which has no FireWire ports at all, I can clone and reboot from the clone just fine using USB3. The OS doesn’t seem to be a factor (last version of Sierra on all three). I’m using SuperDuper so I don’t have any idea whether or not Carbon Copy Cloner does the same thing.

  • Besides having redundant backups, I only do system upgrades at the end of the day, when I don’t need the machine until morning. Stuff happens. And even though it’s unnecessary, I always restart the machine before upgrading. I believe it cures a multitude of evils.

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