Running two MacOS versions simultaneously?

Hi, I’m looking for a little bit of help for my partner. He’s a typeface designer whose primary tool is the software Fontographer. Unfortunately this is a 32-bit app and the maker Fontlab have said they will not be making a 64-bit version. Although there are alternative tools for creating typefaces he’s reluctant to move away from Fontographer because the drawing tools are superb.

All of the above means that he’s stuck on Mojave 10.14.6, but feels like he’s missing out on newer OS features.

Would it be feasible to upgrade to Ventura and run Fontographer under Mojave using Parallels or VMWare? Or is there some other option that we’ve not considered?

For hardware context he has a 5K iMac, 16 GB Ram with a 1TB SSD (half the disk space is free).

To be honest @leanda, while he may wish to stay on Fontographer, it sounds like the app is not going to be supported going forward (MacOS will only run 64bit apps now as you know)

If I were in the same situation, I’d be looking for a new tool so I could make the transition on my own terms, rather than when something happens which renders the software unusable, e.g. The software refuses to run for some reason or his iMac dies and he wants to buy a newer computer which will definitely not support his legacy software.

If he decides to persist with Fontographer, I’d definitely test whatever interim solution he goes with (e.g. virtualisation) to ensure it works BEFORE upgrading in case there is something which stops this from working.

Other options may be to buy an old Mac Mini or something similar to run the older software on.

The largest risk of staying on older OS versions is security, so I wouldn’t see this as tenable long term.

Sorry if that’s not much help.


This is an excellent suggestion!

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Especially as the OS ages out, the less information on that box the better.

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I agree. But it should be reasonably secure if, once the Mac no longer receives updates, the computer is removed from all networks. And files are transferred via external media.

Agreed, but would you stake your business and income on that long term? I know I wouldn’t.


I did. I used a dozen Windows XP PCs, that were used to run one custom program, for 2 or 3 years after the last support update.

(They were base model Dells. Over the years I replaced mice & keyboards as needed and replaced the CRTs with LED screens. But, as I recall, none had a single hardware problem in 9+ years of use )

Thanks for your thoughts. This is really useful information. Eventually he’s going to have to concede to learning a new tool, but we do actually have another 5K iMac that we could silo off from a connected network. I might also try a test with Parallels to see how it runs in the interim.

It should work with Parallels without any big Problems, I had an 32-Bit Instance on my iMac some time ago too, for a similar reason.
But you should be aware, that even running as a VM, it remains a security problem, to run an old OS on your system.
If I would do that for a living, I would also look for a modern software to move on with that, at least on a mid-term base.

for example has some software, that might be worth a look for that.

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Have to agree with the sentiments above, it’s time for Fontographer to go night-night.
Fontlab that @Ulli linked above is from the same company, and the intellectual heir, if you will. They also offer a baby step up to V7 for a lower price than V8.
Probably easier/better to make the switch than jump through all the hoops of getting an old system to work, wonder when it will fail, sneaker-net files back and forth, etc.


You can run macOS in a VM on a mac, so it’s an option.
However my suggestion would be to get hold of a cheap older mac mini or something, like @geoffaire said, to run the application and just rdp/screenshare into that one if he needs to use the application.

Having the older mac connect only to the internal network should prevent most of the security issues

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I recently migrated a (small business) customer’s business-critical software from an early 1990s MS-DOS PC to his MacBook Pro. :wink:

Also, many people would be surprised how many decades-old legacy applications (and sometimes hardware) are still running in some enterprises. But they’re usually (more or less) professionally managed by IT.

That said, the OP’s partner is designing “software” (fonts) and while typography is probably rather “conservative” in their file formats, there’s a good chance this may not be sustainable for too long.

I don’t it’s going to be a meaningful security issue, as long as he doesn’t access the internet from within the guest operating system (which isn’t difficult to prevent, when you can just disable it in network settings for the VM) or opens files from external sources.

It’s good to be aware of risks but I don’t think it’s going to be a showstopper here. I’m sure distribution of malware through font files is theoretical possibility - but I doubt that distribution of macOS-malware through font files isn’t really a thing in the real world (and you can still scan files on the computer connected to the “outside world” that you receive them on).

I’m on Mojave for 32-bit apps myself. I also design software for a living. So I’d like to recommend a certain mode of thinking about this. Remember that the computer is a tool. Does upgrading it make it the best tool for him? Doesn’t sound like it. Sounds like he already has the best tool for his primary usage, and upgrading would distinctly blunt it for some white whale possibility of aggregating sufficient improvements in the margins to balance or tip the scale. Ergo… Stay on Mojave.

Even if you eventually have to give it up because the sands of time have eroded every Mac capable of running it, the time between now and then, is only more time for better alternatives for Fontographer to come out. No reason to give up your best tool preemptively.