Two weeks on OCLP & Ventura on a Late 2009 iMac. Here's what I learned. (Long Read)

For reference: Late 2009 iMac 27", Core i7 @ 2.8GHz, 32GB RAM, AMD Radeon HD 4850 (512MB), 2TB SSD.

I'm the type of guy who very much follows the "if it ain't broke" philosophy. Whenever people ask me if they should buy a new computer my first question is always, "Does your current computer do everything you need it to do, at a performance level you're comfortable with?" Their answer determines my answer. I've been running this iMac (with that RAM and SSD spec) on 10.12 since 2016, upgrading in 2017 when 10.13 came out. Never had any problems with it and it always did everything I needed it to do. Until a few months ago, anyway. I have a Cricut machine and a few months ago they updated the software and broke 10.13 compatibility. For awhile I was able to work around this by reverting to an earlier version of the app (yay, Time Machine!), disconnecting the ethernet cable when I launch the app, wait for it to time out, then reconnect the cable and it worked. Then they flipped a switch on the back end and that broke after about two months. I then fired up a virtual machine with Windows 10 and ran it that way, but that was more annoying than anything else. Then other little things started appearing; the Discord app could no longer be used, forcing me into the browser. Several other apps kept giving me little "reminders" that support for 10.13 would be ending soon. The writing was on the wall.

So after considering a new Mac mini-based system for about $2500 (with monitor) I said "fuck that" and looked towards OCLP. It took me several weeks to get everything worked out.

My biggest hurdle was going to be Adobe Creative Suite. Under 10.13 I ran a 'modified' version of Adobe CS6, specifically the desktop publishing trio of InDesign/Illustrator/Photoshop. These would not run well (if at all) on any newer OS so I needed to find a solution. Not only that, but the solution had two sides: certain versions of CS required certain versions of macOS. It was no use upgrading to a version of macOS that I couldn't get a running version of CS, nor was it useful to have a running version of CS if I couldn't run the OS it needed. After some digging I settled on the combination of macOS 13 (Ventura) and Adobe CS 2021 as that seemed to have the highest compatibility and least amount of issues.

Step one was to make sure my iMac could run Ventura. I used a spare USB SSD to install Ventura via OCLP. The install took awhile but eventually I got there. One thing that was immediately apparent was macOS's transparency effects were fucked. I didn't much care for them anyway so I disabled them in Accessibility and that issue was resolved. Over the next few days I put the Mac through its paces, trying to get it to crash. It was surprisingly solid and never crashed once. It was amusing/interesting to see newer macOS features on my dinosaur, like Dark Mode.

I also thought I was going to have some compatibility issues with my old printers -- a Brother laser printer from 2011, a Dymo label printer from 2009, and a Zebra LP2844 label printer from 2002 -- but I had minimal issues here. The Brother was readily identified by macOS and I didn't have to install any drivers. The Dymo did require me to install drivers first but once that was done it too worked perfectly. The Zebra was a little tricky. There's no driver available for it, and you need to configure it manually through the CUPS system. I did have to do this under 10.13 as well but I had done that so long ago that I forgot and had to look it up again. The short of it is, via the Terminal you have to enable both Apache and the CUPS web interface. Once you do that you can open a browser window, enter CUPS, and manually connect the printer (at which point it appears in the Printers preference panel like any other printer). Once that's done you can disable Apache and CUPS web interface through the Terminal and it's good to go. My Cricuit works perfectly with the current software. Even my Brother P-Touch had no problems with the current software.

Once I was satisfied with Ventura's stability I focused on Adobe CS 2021. I needed to be sure I could install and modify CS 2021 to let it run, but I knew enough about Adobe's practices to know that if you fail to install it properly the first time, it's often neigh impossible to do it again without a clean install. So I wound up in a cycle of installing Ventura, installing CS 2021, trying it out, failing, reformatting, and trying again. Took about a half dozen cycles before I found the secret sauce; if anyone is interested it's in my post history. :-)

Now that I had Ventura and Adobe worked out, the trigger was just begging to be pulled. I made sure my clone and my TM backup were up to date, rebooted from my Ventura installer, held my breath, and wiped my 2TB SSD clean. Installing Ventura went quite a bit faster over the SATA interface and soon enough my iMac was on Ventura. I spent a few hours running system updates, installing software, making sure everything was how I wanted it, etc, then connected my clone drive and copied ~920GB as an overnight transfer. The next day I moved things around and then let it do all kinds of housekeeping -- sync my email, update my Photos library file, etc.

I've been running this for about two weeks now and have literally zero complaints. This is undoubtedly the biggest duct tape computer assembly I've ever run full-time; a modified macOS and 'modified' Adobe CS 2021 on a 15 year old computer. I was expecting crashes and weird bugs and unexpected things. I was expecting apps that wouldn't run under 10.13 to say "hey, even though you're on a newer OS your Mac is too old and slow for this so I'm not gonna run!" But no, it's been pretty close to flawless. I'm now running current versions of every app I need, or at least current enough to remain useful to me, and nothing has ever complained.

Pretty close. Here's a few things I have noticed.

• For some reason, keyboard repeat didn't work at all. I could hold down a key forever and it only ever produces one character, though the accented character pop-up appears. My key repeat rate is set all the way to the right ("fast") and my delay until repeat is set one notch from far right ("short" minus one). The time it takes before the accented character pop-up to appear is adjusted with the delay until repeat setting. This is apparently a Ventura issue, not an OCLP issue. Going into Terminal, typing "defaults write -g ApplePressAndHoldEnabled -bool false", hitting RETURN, then logging out/in again solved this problem for me.
• VirtualBox 7 doesn't run. Or at least, VB7 runs but no virtual machines will run within it. No matter what, they crash. This apparently is an OCLP issue as I've seen a lot of people talk about it but haven't been able to find a solution for it yet. This isn't a deal breaker for me as I have other ways to run Windows, but it is convenient to run a virtual from time to time. I'm hoping that someone will figure this out soon.
• I need a good font management utility for Ventura. I know Font Book exists and it's fine for casual users, but I have literally tens of thousands of fonts. (It's a sickness.) In the past I've used Suitcase, then FontExplorer, then FontExplorer X which is what I was using under 10.13. Suitcase Fusion is now Connect and at $150/year I shout a hearty "fuck you" at Extensis. I recently discovered TypeFace 3 and I'm exploring that. It doesn't seem quite as robust as I'm used to, though it has some interesting features to it.
• Compared to 10.13, Ventura is a bit laggy. Not unusably so, but there's definitely less of a snappy response when using it. The desktop takes a millisecond too long to appear when I hide all windows, for example. There's no single process or program that's causing this so I'm just chalking it up to "newer OS, more features, more code, more load on my computer". Still, given what I've gained from this upgrade versus this tiny sacrifice? Worth it.
• There are occasional graphics glitches. I don't play games on my Mac so I can't attest to that but every so often I'll see a window flicker before closing or refreshing, or a shadow moves ever so slightly out of sync. It's only noticeable because it never happened under 10.13; it's just enough to remind me that I'm pushing my luck. :-)

I plan on performing similar surgery to my daughter's 2014 iMac and perhaps her mother's 2013 MacBook Air. I'm more demanding than either of them by far so I suspect it'll be easier going, but now that I know it's not only possible but reasonably easy and runs well/stable I'm more than happy to give it a go.