vDos, by Jos Schaars, is by far the most useful and well-designed software for running 16-bit DOS applications (not games) on modern Windows systems. It cannot be ported to the Mac (or any other non-Windows system), but it can be used on the Mac under Wine, the software that makes it possible to run Windows applications under macOS.
This page links to an experimental version of vDosMac, an application based on Wineskin Winery, which runs vDos under Wine in macOS High Sierra, Mojave, Catalina, Big Sur, Monterey, Sonoma, and probably later versions.
After downloading the ZIP archive and (if necessary) extracting the app, move the app to another folder, to avoid a macOS security feature that will display a long error message if you try to open it without moving it first. You can move it back to its original folder, but you must move it somewhere before opening it. Don't waste your extremely valuable time writing to me about the "AppTranslocation" error that will appear if you ignore this instruction! Instead, follow the instruction.
After you have moved the app, Ctrl-click or right-click on it and choose Open. The OS will probably tell you that the app is damaged or can't be verified. Click Cancel, and, once again, Ctrl-click or right-click, and choose Open. This time the application may start up correctly.
The first time the application starts, macOS may display an error mssage saying that the application can't run for an unexpected reason. Click OK and start the app again.
When the application starts, you may need to wait as long as two minutes before anything happens. You will be prompted to give permissions to the app; click OK at these prompts if you want the app to work correctly.
You may see various error messages, perhaps about a file or folder that does not exist. The best thing to do is to click OK for each message, then close the application and start it again. It may run normally the next time.
Please do not waste your valuable time telling me about the error messages; I already know about them. Only write to me if you can't run the application after following all the instructions on this page. Yes, I mean all the instructions.
If macOS absolutely refuses to open the app, do this. Open a terminal window adenter:
and then a space. Don't forget the space! Then drag the app into the terminal window and press Enter. The app should now run.
If you see a nag screen from vDos, then go to the vDos site and register the software. You will need to go very deep into the folder structure of the vDosMac app, then into the vDos app inside the vDosMac app, to find the vDos program folder and copy your vDos license into it. But if you are using this software, you should be able to achieve this without my help.
Here is the link to the experimental version of vDos for the Mac:
Drive C: in vDosMac: Drive C in vDosMac is the vDosDisk folder inside your user folder. Add files to this folder as needed.
Note: For applications like XyWrite that will not run under vDos, you may try this experimental DOSBox-X-App, which is a macOS version of DOSBox-X wrapped in an AppleScript that supports printing, etc. Drive C: in the DOSBox-X-App is the DOSBoxDisk folder inside your user folder. Add files to this folder as needed.
Edward Mendelson (edward [dot] mendelson [at] columbia [dot] edu).