Prologue

A friend on Facebook mentioned that he wanted to play some games on his Mac to help with an inner ear problem (practicing with virtual motion apparently helps with vertigo from real motion) — I had suggested Portal, as that’s a very changing-viewpoint-intensive game. Unfortunately, neither of us knew that Portal and Portal 2 are both 32-bit apps, and so they don’t run under more modern Mac OS X’s — anything past Mojave dropped 32-bit support. I said, “I’m sure there’s a way I could make this work.”

Hubris.

They don’t call it Boot Camp for nothing

My initial thought was, well, of course most games run best under Windows; why don’t I set up Boot Camp on this machine? I’ve always wanted to see if it would work.

Well, it might. But the machine I have to play around with — a 2011 MacBook Pro, the last one to have user-upgradable memory and disk — does not play well with modern versions of Boot Camp. See, modern versions of Boot Camp assume that you’ll be able to build a Windows installer USB stick and boot off that to install Windows. Boot Camp does build the installer USB stick; it’s just that my 2011 MBP can’t boot anything except OS X from USB. It could install from DVD, but a) I had no DVD blanks on hand and b) newer Boot Camp does not believe in DVD drives. There’s no option to tell it “please burn this to DVD”.

I started exploring other options, trying to find one I wouldn’t feel like an utter heel trying to convince a not-so-technical friend to use, and there just wasn’t one. The closest I got was building a Windows VM, but that started getting messy and I decided if this was going to work, it needed to work with the tools that a typical Mac user would have, and shouldn’t require the installer to understand how to mount ISOs on virtual machines, and worse.

Dual-wielding Mac OS installs

My MPB can run 32-bit OSes, so I decided that the simplest possible option was create a second partition on the internal HD and install Mojave (the last 32-bit OS X) on it. This was a less complex option by far; the worst it required was a little work in Disk Utility to create the target partition, and issuing one command in Terminal.app to create the installer USB (which yes, my MBP would boot, since it was OS X).

This article was really helpful in getting it done; I won’t repeat the whole thing here, but just mention the highlights:

• Modern Mac OSes use APFS, and creating an extra APFS volume in free space on the internal drive only took a couple minutes.
• Links to older version of OS X are available through this Apple support page; because Apple does get rid of older OSes, I recommend getting the installer you want and backing it up in case you ever want it again. Currently (as of May 2021), you can get Catalina, Mojave (the last 32-bit OS X), and High Sierra as installer apps from the App Store, and Sierra, El Capitan, and Yosemite as .dmg files, which install the installer. Older versions are probably available out there on the Internet, but they won’t be official Apple source.
• Creating the installer is the one more-sophisticated step, in that it requires you to enter a command in Terminal.app to create the USB stick. That’s documented in this Apple support document; it’s only one command, so it’s not too scary.
• Once you have a usable USB stick, it’s relatively straightforward. Boot the machine while holding down the Option key, and you’ll get a menu of disks to boot from. Pick the installer USB. You go through a couple screens to get to the install disk; pick the APFS partition you added.

The result

That’s pretty much it; wait for the installer to do its thing. One it’s finished, you’ll be up in Mojave. If your Catalina or Big Sur install is on an encrypted disk, you’ll get a prompt to enter your userID password from the other install; note that there are two partitions it will have to unlock. The first will use a bizarre dashed-hexidecimal username; if you’ve got more than one user, you’ll have to try combinations of different weird usernames and your login password until it unlocks. The second will use your regular username. (You can have Mojave remember these so you won’t have to enter them again.)

And now you’re up on Mojave! Note that since your Catalina/Big Sur install is readable, you can run applications that are installed on that system in this one without reinstalling them. In this case we want to run Steam, which runs just fine and allows you to install Portal to the Mojave partition and run it there.

This still isn’t as simple as having an OS that supports both 32 and 64 bit apps, but it will work. If you’ve got 32-bit apps you really need to keep, then this is a way to have the best of both: the newest OS and one that still runs all the things you need.

Time to clean up!

Earlier this year, my company, in its push to get things squared away for an IPO at some point (note to the SEC: I know nothing about IPO plans, I am not suggesting anyone invest in anything, I’m just this guy, you know?), installed a remote management tool for MacOS. Initially, I was concerned that we might end up being monitored as to what was on our machines, and non-work use might be frowned upon – plus I learned the hard way at WhiteHat that if you’re going to get laid off or fired, no one’s going to give you a day or two to back up anything personal on your machine. (I lost, and later managed to partially recover, all the patches for my Radio Free Krakatau album.)

IT and upper management, after a couple of days of general consternation and concern about keylogging, etc., formally told us, “no, we don’t care what you do on your laptop, just don’t do anything illegal,” but by that point I’d scoured off the personal files and data and moved them to iCloud, Dropbox, or a spare 2012 MacBook Pro I had.

The 2012 MBP was the last one that allowed upgrading by the end user. It could accept up to 16GB of memory, had a lot of ports (including a DisplayPort, native Ethernet, and FireWire), and had an internal disk that could be swapped to an SSD.

I picked up a 2TB Crucial SSD, pulled the old disk, installed the new one, and used Carbon Copy Cloner to copy the old internal disk back on to the SSD. I also pulled in several older backup spinny disks into a folder called “Backups to Clean Up”. This was a superfund site of duplicates, junk, and accumulated files. I took a first cut at cleaning it up right away — deleting old stuff I knew I didn’t care about anymore, like partial iPhoto/Aperture/Photos libraries and old iTunes folders — but I was left with a considerable stash of data that I knew contained duplicates. At the time I was busy and decided I’d work out the rest later. I had removed my Adobe apps and music apps and data from my work laptop, and at the time I just didn’t have any time to work on those.

Diving in with Gemini II

Last weekend, I decided it was time to do the cleanup. I had bought Gemini II a couple years ago in a MacHeist bundle, and had tried it a little, but found it too slow on a spinny disk to to be useful. I decided that the job was big enough that I really needed to have some help, so I tried it again. I fired it up on Wednesday afternoon, and pointed it at my home directory on the MBP, and said go get ’em.

Friday morning (I neglected to exclude Dropbox from the duplicate check, resulting in a lot of “download the file, check it” for the 200 or so GB or data in there, slowing things down considerably), I had a complete comparison. I spent the better part of Friday evening and Saturday and a chunk of Sunday looking at the recommendations and clearing duplicates. In general Gemini had made good choices as to which files to keep and which were duplicates, and this got rid of almost 200GB of duplicates. I did a couple rescans and found another hundred or so that I could clean up.

Gemini recommended I try CleanMyMac X to help with getting rid of extra junk on the disk, and being in a cleaning mood, I decided to try it. I signed up for a month, and only after I’d done that did I see a “30% off if you own one of our other products”, despite being signed in. MacPaw was very kind and extended my CleanMyMac X subscription for three months to compensate.

On the initial run, CleanMyMac X was very useful. It cleared a bunch of old caches, got rid of unused languages, etc., and helped me cleanly delete some old apps that were cluttering up ~/Library. It installed a very attractive cleanup and virus checking monitor, and I thought nothing of it at the time.

Problems surface

I continued working with Gemini II, and the monitor was solicitously clearing the trash when it got full, and so on. I then tried to use Gemini to just dedup my Music folder, and here’s where the fun started.

It ran for an hour or so and then I got a “You are out of memory” warning; Gemini II apparently had 69GB of memory allocated. I shut some stuff down, but I ran out of memory again. And again. And again. Quit Gemini. Tried to run Ableton Live; the cursor was sluggish, sound was breaking up, and trying to select a patch in plugins was causing outright crashes. And the laptop was so hot I couldn’t leave it on my legs.

This was not going to do at all. I wanted to use this machine for music, and it wasn’t able to handle it anymore. Was I going to need a new laptop? It was late. I went to bed.

The solution

In the morning, after some time spent with Activity Monitor, I twigged to the problem: CleanMyMac X had installed a lot of startup items. Like four. And Gemini had installed some too. This was not going to get any better with those hanging around. I decided that I was going to have to remove them, and the easiest way was to have CleanMyMac X do it. All credit to MacPaw: it simply warned me that it would shut down all the monitoring if I removed CleanMyMac X, did I want to do that? I did.

And now the machine is running fine. I’m able to keep a couple of instances of Arturia’s 2600 emulator open and running with Live actively generating sound, and I can tweak the settings without significant effort or the sound breaking up. I ended up using Song Sergeant to do the Music Library cleanup; I can recommend it as doing a good job of finding duplicates, even in different formats.

Conclusions

The machine is slimmed down by about 250GB total and running fine; if I decide to do a similar cleanup again, I will probably use both Gemini II and CleanMyMac X to get the cleanup work done, but without being able to easily say no to the monitoring they install, I’ll probably delete them again as soon as I finish. MacPaw, if you’re reading this: make it optional to install the startup items, and give us an easy way to turn them off. If I had those I’d leave the two apps installed, but I just can’t and get any work done.

You cannot drag and drop .m3r files into the Tones tab in iTunes. They must be pasted.

Find your .m3r files in the Finder, select them all, File > Copy, click on the Tones tab in the iTunes sidebar, and File > Paste.

No, it does not make any sense that drag and drop does not work. But it absolutely does not.