The Snowball Effect in Florida: Upgrading to High Sierra

Yes, you can have a snowball effect in sunny Florida! I know this because it happened to me this week. What started as a simple need to install a software program gradually grew into a larger, more complex series of events.

Applications and System Requirements

I am teaching my Graphic Design 2 class remotely this semester. That’s because my students are in Newton, Massachusetts and I now live in Florida. One of the more promising tools I was considering for video conferencing—Skype for Business—requires Mac OS X El Capitan and higher (see system requirements). My Mac was still using Yosemite. OK, no problem, I thought. I’ll just upgrade to El Capitan, which is the next OSX in the sequence:

• OS X Mountain Lion – 10.8
• OS X Mavericks – 10.9
• OS X Yosemite – 10.10
• OS X El Capitan – 10.11
• macOS Sierra – 10.12
• macOS High Sierra – 10.13

I quickly discovered that El Capitan and Sierra are no longer available as downloads in the Apple store. None of the download links I tried for them worked. My only choice was to upgrade directly to High Sierra, which made me nervous not only because it would be jumping up 3 levels, but also because High Sierra is based on a new 64-bit architecture. That meant at least a few of my software applications would be incompatible and I’d have to upgrade them as well (i.e., dish out some money). At least the OS X upgrade was free.

Backup Computer Files

Upgrading my operating system is not a common task for me, so I read all of the information Apple provides about how to do it (https://www.apple.com/macos/how-to-upgrade/). The most emphasized recommendations are to back up your computer and create a bootable disk in case you need to restore the operating system. I’ve had a backup procedure in place for years that is 3-tiered: (1) Manually back up all files to an external LaCie drive (which uses the FireWire port and is very fast); (2) Manually back up all files to an external USB drive (much slower than the Firewire device); (3) Automatic daily backups to a cloud service (I use iDrive). So, I made sure all of my backups were current.

Even though I had learned about bootable disks years ago, I neglected to ever follow through and create one. I was determined to follow through this time. Of the many ways to create a bootable disk, I decided to use Disk Utility, following the instructions in this article: Back Up Your Startup Disk Using Disk Utility.

Flash drives are not recommended by some people. Since my LaCie FireWire drive and Western Digital USB were already being used for regular backups, the only other non-flash external drive I had was a Seagate USB. I plugged it in and verified it with Disk Utility. Everything looked good to this point. However, it didn’t pass the disk permissions test, because it was PC-formatted. No big deal. I reformatted it as Mac-based with the “Mac OS Extended (Journaled)” option. Reformatting a disk erases all of its contents and configures it to be entirely Mac-compatible. It was quick and easy.

I returned to the task of creating the bootable drive. Disk Utility still wasn’t happy and wouldn’t complete the cloning. It turns out that reformatting wasn’t sufficient:  I needed a new cross-platform utility that would enable my Mac to read AND write to the drive.

Paragon NTFS was installed, then I went back to Disk Utility. Now it suggested that I create a partition on my “Destination” drive (the newly Mac-formatted USB drive). Huh? More research revealed a partition tab that I was supposed to select, but that tab didn’t appear in my Disk Utility. Roadblock.

Sometimes, trying something over and over again with subtle changes in the approach will actually work. Maybe you missed a step or typed the wrong letters or misunderstood an instruction. Sometimes, though, it’s better to change the approach and try something different. There is always more than one solution.

I decided to try another utility. More research ensued. This article provided good guidance: No Excuses: 7 Free Mac Backup Apps. I was familiar with SuperDuper, which was effective, but it received tepid reviews and had a clunky interface. The tech community was more enthusiastic about Carbon Copy Cloner, so I installed that application and launched it. Warnings were issued about the external drive and possible difficulty using it as a reliable backup. Yet, this program offered me the option to proceed with caution. I did exactly that, and I’m glad I did. The process was much quicker than I thought it would be.

A few days later, I came across this information:

Beginning with OS X El Capitan, system file permissions are automatically protected. It’s no longer necessary to verify or repair permissions with Disk Utility.” – Apple Support

Hmmm… is that why the permissions repair didn’t work and I never saw the partition tab? Maybe some day I’ll have the answer.

High Sierra Upgrade and Incompatible Apps

It was nearly a full day of dealing with the backup and cloning. The following morning, I upgraded to High Sierra. It took about one hour. No issues arose. Things will likely go smoothly for you, too, if you take the time to minimize problems.

I knew Quickbooks would be an issue. Sure enough, my version was not compatible with High Sierra. More research. I had an online chat with a Quickbooks sales rep and found out that Quickbooks 2016 for Mac would automatically import my data. If I decide to go with a cloud-based QB later, I can migrate to that. I bought the QB 2016 for Mac, installed it, launched it, and opened my most recent QB file. The program automatically imported the data and all was well.

Next, I discovered that my fonts manager, Fusion, was incompatible. I was in the middle of a print project, too! Yikes! No problem, I simply used Font Book, a native Mac application. I mostly do web stuff now, so Font Book fits my needs.

Finally, I was able to load the software I thought I’d be using for my class: Skype for Business. I had a test session with a couple of colleagues. The interface and features were great. One big drawback was that the other participants couldn’t hear me. I could hear them, but no matter what I did with my sound settings, they couldn’t hear me. What a huge disappointment!

I searched Microsoft’s Skype help forum (MS purchased Skype in 2011). There were a lot of complaints about the sound. Great, I’m not the only one! Then, I remembered trying to use Skype Meetings a few months ago and having difficulty with the sound: they could hear me, but I couldn’t hear them. That was the final straw and I had had enough of Skype.

Ironic isn’t it? My entire journey down the High Sierra lane began because I wanted to use Skype for Business and now I want nothing to do with it. On the positive side, I can now use other applications that were not compatible with Yosemite, notably Adobe XD, for mobile UX design and prototyping. I’m pretty psyched about that.

Video Conferencing Tools

One last thing. My search for a video conferencing tool continues. The features I am looking for are:

• Free
• At least 10 users
• At least 90 minutes in length
• Video conferencing: students need to see me and I need to see them.
• Audio: we need to hear one another 🙂
• Screen sharing
• Presenter-switching
• User-friendly interface
• Easy installation

I landed on 3 strong contenders:

1. Free Conference Call
   I’ve tested this with several colleagues and really like it.
2. Uber Conference
   Still to be tested: stay tuned!
3. Ring Central
   Provided by my school. We need to check on the system requirements and plan offerings.

A future blog post is brewing on this subject!

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