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The Power of Patience: Installing High Sierra at Last Share This on LinkedIn   Tweet This   Forward This

18 September 2019

Apple's release of macOS 10.12 Sierra has been one of its most reliable but the promise of High Sierra dotting Sierra's i's and crossing its t's was something we looked forward to after it was announced. And until High Sierra was actually released, quickly gaining a reputation as a step backward rather than forward.

Hiking to High Sierra. We wanted to take our Wacom Intuos along and, to our surprise, it was no problem.

That was centuries ago in operating system time. In fact, we published Wacom Tablets Incompatible With High Sierra in Sept. 2017. And no update was ever released.

Because we're quite attached to our USB Wacom Intuos 2, we stuck with Sierra without regrets.


We're not Luddites when it comes to upgrades. We let our applications including Adobe Creative Cloud, update themselves immediately. And we don't sit around waiting for iOS update reports to trickle in either.

In fact, it's just macOS updates that make us wary. And that's because we have created an ecosystem of some cherished and very useful tools that plug into the operating system.

They aren't just hardware tools like the Wacom (or external hard drives and card readers). They're also software tools, like our LAMP-like development environment that runs PHP, Perl, Apache, MySQL and a few other ancient (and free) utilities.

We're amused by the people who rush to install the latest macOS betas (that would be the unfortunately-name Catalina at the moment) or even the early releases of gold masters (like Mojave). The new features seem a negligible enticement compared to the risks to productivity.

It reminds us of the cool kids in grammar school who always wore the trendiest clothes and had the new hairstyles but really didn't accomplish anything other than form a club called Detention. While the kids who wore glasses to see the blackboard and did their homework and stayed out of trouble remind us of the more cautious people who take their sweet time to upgrade because, you know, they have work to do.

But features are just the candy to attract the cool kids. What's going on under the hood is the real story. And that's usually the introduction of new technologies that are not compatible with older ones. Like more intensive GPU processing, memory management strategies or new storage schemes that obsolete older equipment.

Our Mid 2010 17-inch MacBook Pro is our daily workhorse. And our Early 2011 13-inch MacBook Pro is our travel machine. Neither are upgradable past High Sierra because of those hardware requirements. And both lived very happily with Sierra with an SSD in the 17-inch (maxed out at 8-GB RAM) and 16-GB RAM in the 13-inch.

We thought we were done with upgrades.


But then two applications we could not ignore required at least macOS 10.13 High Sierra. So we had to reconsider our position. Fortunately, we were in the right frame of mind.

Just a few weeks earlier, we had spent a morning rearranged three three power strips and one power conditioner connected to one outlet to accommodate an old Bluetooth smart plug that had been replaced by a couple of WiFi smart plugs.

Reconfiguring our outlets was a puzzle but it didn't hurt to revisit our 16 year old installation.

In fact, it went very well. All the old stuff worked and we had new tools with the three smart plugs.

That success put us in the right mood to update the 13-inch, testing the Wacom and our critical applications on it before deciding if we should upgrade the 17-inch as well.


After backing up the 13-inch, we found the link to the High Sierra download on the App Store (which is not readily apparent) and proceeded with the update on, of all days, Friday the 13th. We hadn't noticed.

From start to finish it took five hours, running into Saturday the 14th. We took that as a good omen.

Then we went through our checklist:

  • Adobe CS5 Support. We still keep CS5 applications installed because they are the last non-subscriber versions of the Creative Suite. We did have to download and run the Java SE6 Runtime installer to provide support, as we have in the past.
  • Enabling PHP. We had to enable PHP in Apache's config file, as usual after any OS upgrade. That simply requires uncommenting one line. But this time it opened a can of worms because High Sierra installs PHP 7 rather than the previous PHP 5. High time, some would say.
  • Check Apache, MySQL. Both Apache and MySQL are always running on our machines and bot Apache and MySQL were activated just as if nothing had changed.
  • ExifTool. We confirmed ExifTool was still functioning. Which would also mean our Perl modules had not been wiped. They've been safe with recent updates, a change in policy from the days when an OS X upgrade would delete any user installs.
  • ImageMagick. We also confirmed ImageMagick was still accessible.
  • Wacom Intuos. To our delight, we were able to confirm the tablet still functioned just as it had under Sierra. We did have to reinstall the last working driver (which Wacom does not support on High Sierra) and quit (not restart) to get control of the cursor but both mouse and pen functioned. We note that Wacom no longer sells a tablet with both a mouse and a pen (just pen tablets now), which would have been a loss for us (mice tending to stay where you left them while pens like to roll onto the floor). We also should note that no reinstall of the driver was necessary on the 17-inch, where we usually use the Wacom, when we subsequently updated that.
  • Warnings. When we rebooted into our new macOS, we did get a couple of warnings that some older software was not "optimized" for High Sierra. On subsequent reboots, though, the warnings were not repeated. And the software did run.
  • Subsequent Updates. There were updates to Numbers, Photos, iMovie and Keynote as well as a Security update to add after the macOS update. We did those without delay.

Much of this testing was made immensely easier by Keyboard Maestro, which runs a number of things for us. It's rock solid itself through Mojave at the moment and does all our mundane tasks for us (mounting externals, archiving files, uploading files to the site, spell checking, searching directories, image editing, etc.). It was reassuring to see it running our macros just as they had always run.

One thing we did not do was shut the machine down to do a cold restart. That's never a bad idea after an update because it rechecks the hardware environment (USB drives, etc.). We've since done that without issue.


We did scratch our head over two puzzles, one of them serious enough to postpone any immediate update of the 17-inch MacBook Pro:


The first was that buttons on a Custom HTML Form in Keyboard Maestro which used emoji did not display in High Sierra. They showed up in Sierra and also appeared in a Custom HTML Form outside a button. But not on a button.

To resolve this we had to include the Apple Color Emoji font in the CSS style declaration for the button.


The move to PHP 7 meant that interacting with a MySQL database now required using MySQLi extensions rather than they old MySQL extensions of PHP 5. For the most part this simply means adding an "i" to function calls. But some functions require another parameter and some old MySQL functions just never made it into MYSQLi (because, say the doyens, "you don't need them").

We have a couple of applications that run MySQL databases and they're critical ones here. So we spent one night updating the function calls. That worked for one application.

But the missing functions were a problem that took a couple of days to solve for the other application. We managed that Monday afternoon.

We also had to rewrite the code that displays how long it's been since we updated the headline page on the site. And since the site runs on an older version of PHP, we had to write code compatible with both versions of PHP.


By then we were confident enough in our Saturday and Sunday morning runs of High Sierra on the 13-inch MacBook Pro to install it on the older 17-inch MacBook Pro.

So Sunday afternoon we did that. It took a bit over an hour. That surprised us but it may have been because that larger number of files inhabits an SSD rather than a spinner.

And Monday morning we came to work using High Sierra.


Frankly, we're glad we waited. High Sierra is at 10.13.6, a matured product with only security updates in its future, apparently. And the applications we care about have now been updated tot function in even later macOS versions. So it was never a safer time to make the move.

But, frankly, High Sierra provides no feature we missed in Sierra's long run here from April 2017 or Yosemite from January 2015. It just lets us run the two applications that prompted the move.

But as the last macOS that can be installed on these MacBook Pros, we hope it has a longer run than any of its predecessors.

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