OT – Upgrading From macOS Mojave To Catalina (The Hard Way)

This post is really about the boring stuff I do when I have a day off and isn’t terribly exciting. TL;DR I had some problems upgrading to Catalina, and had to start from scratch.

 

Background

I’ve had an Apple Mac since around 2008. I upgraded from a 24″ iMac to a 27″ iMac and was super impressed with the process of migrating between machines, primarily because of Time Machine’s ability to recover settings, applications, and data in a fairly seamless fashion. I can’t remember what version of macOS I started with (maybe Leopard?), but I’ve moved steadily through the last few versions with a minimal amount of fuss. I was running Mojave on my iMac late last year when I purchased a refurbished 2018 Mac mini. At the time, I decided not to upgrade to Catalina, as I’d had a few issues with my work laptop and didn’t need the aggravation. So I migrated from the iMac to the Mac mini and kept on keeping on with Mojave.

Fast forward to a April this year, and the Mac mini gave up the ghost. With Apple shutting down its stores here in response to COVID-19, it was a 2 week turnaround at the local repair place to get the machine fixed. In the meantime, I was able to use Time Machine to load everything on a 2012 MacBook Pro that was being used sparingly. It was a bit clunky, but had an internal SSD and 16GB of RAM, so it could handle the basics pretty comfortably. When the Mac mini was repaired, I used Time Machine once again to move everything back. It’s important to note that this is everything (settings, applications, and data) that had been accumulated since 2008. So there’s a bit of cruft associated with this build. A bunch of 32-bit applications that I’d lost track of, widgets that were no longer really in use, and so on.

 

The Big Update

I took the day off on Friday last week. I’d been working a lot of hours since COVID-19 restrictions kicked in here, and I’d been filling my commuting time with day job work (sorry blog!). I thought it would be fun to upgrade the Mac mini to Catalina. I felt that things were in a reasonable enough state that I could work with what it had to offer, and I get twitchy when there’s an upgrade notification on the Settings icon. Just sitting there, taunting me.

I downloaded the installer and pressed on. No dice, my system volume wasn’t formatted with APFS. How could this be? Well, even though APFS has been around for a little while now, I’d been moving my installation across various machines. At the time when the APFS conversion was part of the macOS upgrade, I was running an iMac with a spinning disk as the system volume, and so it never prompted to do that upgrade. When I moved to the Mac mini, I didn’t do any macOS upgrade, so I guess it just kept working with the HFS+ volume. It seems a bit weird that Catalina doesn’t offer a workaround for this, but I may just have been looking in the wrong place. Now, there was a lot of chatter in the forums about rebooting into Recovery Mode and converting the drive to an APFS volume. No matter what I tried, I was unable to do this effectively (either using the Recovery Mode console with Mojave or with Catalina booting from USB). I followed articles like this one but just didn’t have the same experience. And when I erased the system drive and attempted to recover from Time Machine backups, it would re-erase the volume as HFS+. So, I don’t know, I guess I’m an idiot. The solution that finally worked for me was to erase the drive, format it as APFS, install Mojave from scratch, and recover from a Time Machine backup. Unfortunately, though, this seemed to only want to transfer around 800KB of settings data. The normal “wait a few hours while we copy your stuff” just didn’t happen. Sod knows why, but what I did know was that I was really wasting my day off with this stuff.

I also ran in to an issue trying to do the installation from USB. You can read about booting from external devices and the T2 security chip here, here, and here. I lost patience with the process and took a different approach.

 

Is That So Bad?

Not really. I have my Photos library and iTunes media on a separate volume. I have one email account that we have used POP with over the years, but I installed Thunderbird, recovered the profile from my Time Machine data, and modified profiles.ini to point to that profile (causing some flashbacks to my early days on a help desk supporting a Netscape user base). The other thing I had to do was recover my Plex database. You can read more on that here. It actually went reasonably well. I’d been storing my iPhone backups on a separate volume too, and had to follow this process to relocate those backup files. Otherwise, Microsoft, to their credit, has made the reinstallation process super simple with Microsoft 365. Once I had most everything setup again, I was able to perform the upgrade to Catalina.

 

Conclusion

If this process sounds like it was a bit of a pain, it was. I don’t know that Apple has necessarily dropped the ball in terms of usability in the last few years, but sometimes it feels like it. I think I just had really high expectations based on some good fortune I’d enjoyed over the past 12 years. I’m not sure what the term is exactly, but it’s possible that because I’ve invested this much money in a product, I’m more forgiving of the issues associated with the product. Apple has done a great job historically of masking the complexity of technology from the end user. Sometimes, though, you’re going to come across odd situations that potentially push you down an odd path. That’s what I tell myself anyway as I rue the time I lost on this upgrade. Was anyone else’s upgrade to Catalina this annoying?

Random Short Take #31

Welcome to Random Short Take #31. Lot of good players have worn 31 in the NBA. You’d think I’d call this the Reggie edition (and I appreciate him more after watching Winning Time), but this one belongs to Brent Barry. This may be related to some recency bias I have, based on the fact that Brent is a commentator in NBA 2K19, but I digress …

  • Late last year I wrote about Scale Computing’s big bet on a small form factor. Scale Computing recently announced that Jerry’s Foods is using the HE150 solution for in-store computing.
  • I find Plex to be a pretty rock solid application experience, and most of the problems I’ve had with it have been client-related. I recently had a problem with a server update that borked my installation though, and had to roll back. Here’s the quick and dirty way to do that on macOS.
  • Here’s are 7 contentious thoughts on data protection from Preston. I think there are some great ideas here and I recommend taking the time to read this article.
  • I recently had the chance to speak with Michael Jack from Datadobi about the company’s announcement about its new DIY Starter Pack for NAS migrations. Whilst it seems that the professional services market for NAS migrations has diminished over the last few years, there’s still plenty of data out there that needs to be moved from on box to another. Robocopy and rsync aren’t always the best option when you need to move this much data around.
  • There are a bunch of things that people need to learn to do operations well. A lot of them are learnt the hard way. This is a great list from Jan Schaumann.
  • Analyst firms are sometimes misunderstood. My friend Enrico Signoretti has been working at GigaOm for a little while now, and I really enjoyed this article on the thinking behind the GigaOm Radar.
  • Nexsan recently announced some enhancements to its “BEAST” storage platforms. You can read more on that here.
  • Alastair isn’t just a great writer and moustache aficionado, he’s also a trainer across a number of IT disciplines, including AWS. He recently posted this useful article on what AWS newcomers can expect when it comes to managing EC2 instances.

Random Short Take #23

Want some news? In a shorter format? And a little bit random? This listicle might be for you.

  • Remember Retrospect? They were acquired by StorCentric recently. I hadn’t thought about them in some time, but they’re still around, and celebrating their 30th anniversary. Read a little more about the history of the brand here.
  • Sometimes size does matter. This article around deduplication and block / segment size from Preston was particularly enlightening.
  • This article from Russ had some great insights into why it’s not wise to entirely rule out doing things the way service providers do just because you’re working in enterprise. I’ve had experience in both SPs and enterprise and I agree that there are things that can be learnt on both sides.
  • This is a great article from Chris Evans about the difficulties associated with managing legacy backup infrastructure.
  • The Pure Storage VM Analytics Collector is now available as an OVA.
  • If you’re thinking of updating your Mac’s operating environment, this is a fairly comprehensive review of what macOS Catalina has to offer, along with some caveats.
  • Anthony has been doing a bunch of cool stuff with Terraform recently, including using variable maps to deploy vSphere VMs. You can read more about that here.
  • Speaking of people who work at Veeam, Hal has put together a great article on orchestrating Veeam recovery activities to Azure.
  • Finally, the Brisbane VMUG meeting originally planned for Tuesday 8th has been moved to the 15th. Details here.

Random Short Take #17

Here are some links to some random news items and other content that I recently found interesting. You might find them interesting too. Episode 17 – am I over-sharing? There’s so much I want you to know about.

  • I seem to always be including a link from the Backblaze blog. That’s mainly because they write about things I’m interested in. In this case, they’ve posted an article discussing the differences between availability and durability that I think is worth your time.
  • Speaking of interesting topics, Preston posted an article on NetWorker Pools with Data Domain that’s worth looking at if you’re into that kind of thing.
  • Maintaining the data protection theme, Alastair wrote an interesting article titled “The Best Automation Is One You Don’t Write” (you know, like the best IO is one you don’t need to do?) as part of his work with Cohesity. It’s a good article, and not just because he mentions my name in it.
  • I recently wanted to change the edition of Microsoft Office I was using on my MacBook Pro and couldn’t really work out how to do it. In the end, the answer is simple. Download a Microsoft utility to remove your Office licenses, and then fire up an Office product and it will prompt you to re-enter your information at that point.
  • This is an old article, but it answered my question about validating MD5 checksums on macOS.
  • Excelero have been doing some cool stuff with Imperial College London – you can read more about that here.
  • Oh hey, Flixster Video is closing down. I received this in my inbox recently: “[f]ollowing the announcement by UltraViolet that it will be discontinuing its service on July 31, 2019, we are writing to provide you notice that Flixster Video is planning to shut down its website, applications and operations on October 31, 2019”. It makes sense, obviously, given UltraViolet’s demise, but it still drives me nuts. The ephemeral nature of digital media is why I still have a house full of various sized discs with various kinds of media stored on them. I think the answer is to give yourself over to the streaming lifestyle, and understand that you’ll never “own” media like you used to think you did. But I can’t help but feel like people outside of the US are getting shafted in that scenario.
  • In keeping up with the “random” theme of these posts, it was only last week that I learned that “Television, the Drug of the Nation” from the very excellent album “Hypocrisy Is the Greatest Luxury” by The Disposable Heroes of Hiphoprisy was originally released by Michael Franti and Rono Tse when they were members of The Beatnigs. If you’re unfamiliar with any of this I recommend you check them out.