I suggest that you back up that computer with Acronis True image, before you attempt to reinstall Windows. Acronis True image is not free, but it’s cheap, compared to losing everything on your computer. Everyone should be backing up their computers, but sadly almost no one backs up their computers. I worked in the IT industry for decades, and I recovered Windows servers when the servers failed and needed to be recovered. Eventually, every computer will fail. It could be sooner, or later. If you don’t have a backup, all your documents and photos will be lost forever. Windows has a backup method that is free and built in. Sadly, the built in Windows recovery software fails to recover the computer, when you need to recover! That’s why 3rd party backup software, like Acronis True Image exists.

Sometimes, Windows Activation can be a problem. You can almost always get around that problem is you activate Windows by telephone. You will be asked to type in 9 six number blocks into your phone. Then you will be given 9 six digit blocks to enter into your computer. Take a clear photo of the numbers you are given, so you can reuse those Windows Activation numbers in the future if needed. However, it does work to Activate Windows by telephone on the same computer, over an over. After you are done working on the computer, verify that Windows is Activated. If Windows isn’t Activated, your computer will only stay powered on for one hour, before it powers off by itself.

Here is what I would try 1st:
Click on the "Windows Start"
Select "Settings"
Select "Windows Update"
In the left panel, select "Troubleshoot"
In the right panel, select "Additional Troubleshooters"
Scroll down and select "Program Compatibility Troubleshooter"
Select "Run the troubleshooter"
When it finds all your programs, select the program you are having a problem with and click "Next"

Maybe this will work for you.
Good luck!

No option to find a new program to teplace your older one? One thing about software, it keeps getting better and you need to learn to change with it.

Just for what it's worth, as part of my job I used true Image for a long long time, I want to say starting back about 2004. It just worked.

At some point in the last 3-4 years it started not working. It wouldn't boot to the media, the images wouldn't boot, it wouldn't recognize drivers, etc. It became unreliable.

I found a different tool. Macrium reflect. It's free for individual use and for cloning drives. It works. Every time. Macrium Software | Macrium Reflect Free Also, it makes the image while you're booted into the OS! You don't have to boot to a dos loader or some linux loader or whatever. It really is a great tool. I have no connection to this company other than using this software so I'm not trying to foist some malware on you. Get Macrium and try it, you'll thank me later :).

I appreciate all of the suggestions.

The program is NewViews - written for DOS in the 80's and, amazingly, it still runs in native form on Windows 10 32-bit. 64-bit, however, does not include DOS compatibility so it only works by running it within DOSBox or similar, which makes switching between it and other programs (browser or spreadsheet in my case) very clunky. I had no luck getting vDOS to work. I do not want to learn a new accounting program, and it would probably be impossible to import the 30-year history into it.

I travel a lot and bought this laptop to be the single replacement for a small travel laptop and two home desktops, so I really need it to do everything. Toting a second, 32-bit, laptop is not an option.

From what I have read, while it might be a nerve-racking weekend, it sounds as though the conversion and reinstallation of drivers should go relatively smoothly - famous last words!

This is great advice, I too worked in the IT field and what davephan is suggesting what I would do too if I were using Windows. After retirement I moved to Apple devices, they have been trouble free.

Best suggestions from my experience, which is the P in PC, (Personal)
1) Macrium Reflect for imaging
2) Replace any and all disks with solid state drives (now)
Makes them drop proof in laptops
3) Work on compatibility mode / virtualization of a primary laptop

Then replace the dinosaur in the room

tech guy

My wife and I also moved on to MacBook Pro computers. At least 99% of the time, the MacBooks are connected to 43 inch Samsung 4K TV for the monitors, mouse, and Matias Quiet Pro full sized keyboards. However, on trips, we can use the laptops alone. Typing on a laptop keyboard is a royal pain, so the Matias Quiet Pro keyboard is worth the $150 cost, much more costly than a typical Windows keyboard.

I still have a couple of Windows computers around for a couple programs that only run on Windows. But the vast majority of the time, we use the Mac computers, which are a lot less trouble to maintain than Windows computers. After getting used to Mac computers, the Windows computers seem very crude, barbaric, and full of security holes that constantly need patching. I also had to do the constant Windows patching on hundreds of Windows servers.

Unfortunately, Apple Cloud backups only works on iPhones and iPads, not MacBooks. You have to backup with a USB hard drive with the MacBook using Time Machine. Time Machine to the Apple Cloud isn't an option for some unknown reason. I also use Acronis on the Mac to have automated backups in the encrypted cloud. Maybe someday, the Apple engineers will wise up and allow Time Machine to backup to the Apple Cloud, something practical, instead of creating endless Emoji's that people don't need.

I backup my Windows computers with Acronis True Image. We started doing backups and recoveries decades ago with Norton Ghost. Version 7 and later were very reliable recoveries. After I retired, my work switched to another backup recovery method that is less reliable. I think that bare metal recoveries weren't even possible with that other backup / recovery software. Differential hardware recoveries might not have been possible either. I also heard that after I retired, my former company got burned because they couldn't successfully do recoveries. When you're in that line of work, you have to perfect your backup and recovery methods, and actually test your recoveries on "test" servers. We also had redundant backup methods. After a couple decades of that line of work, I never ran into a situation where I couldn't recover a Windows server.

The company I worked for was stupid, and didn't backup each Windows workstation and laptop. Only limited files were backed up. Then when someone's workstation or laptop failed, they lost hundreds of hours of productive work time, while the user tried to re-create their computer environment, programs, and settings from a generic base image. Some companies never learn how important proper backups are for every computer, including workstations and laptops in their corporate environment. They even had some Windows servers, out of my area that weren't backed up or patched, and didn't reboot for years!

I agree. Seems like a lot of work for one program. I would research converting files from old DOS program. As technology improves, it will get harder each time for you to use your program. Conversion of that is your best bet. If you do decide to run the 32 bit, I agree with the others on dual boot.

Good luck on the retrograde upgrade.

I am now remembering sitting in a villages listing service office while the agent Looked for some information on a PC. And you may not believe this, but they were still using Windows 7 less than two years ago. Absolutely crazy.

DOS programs are legacy and specific. They are designed specifically to run on DOS. The computer needs the appropriate DOS drivers behind the windows somewhere, AND that the windows OS will allow the user to access those drivers. Then, it can be jury-rigged to work. Without it, it won't work, period. The only thing you can do at that point is use a DOS emulator, which is slow and clunky.

I cut my computer teeth on BASIC programming, and spent several years working primarily with DOS. I was heartbroken when they removed DOS from windows. There are just some things that flat out won't work without it.

I was using Windows 7 three years ago. And I have set up my Win10 machine to appear as Win95. If I could get win 3.11 back, I would.

You know, there IS a more updated version of NewViews, written for Windows. You'd have to spend some time learning how to adjust to the differences, but it has the same functionality as the DOS version with several significant improvements.

NewViews Accounting – NewViews Accounting Software

Just use ran as on app and choose what operation system you need. No need to uninstall

Before you purchased your new computer did you ask if your old program could be used on any of the new computers?

They might have something you could add.