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Q: I have used Microsoft Money 2006 for at least 20 years, only offline and only for a “check book” and backup for several accounts that does allow me to create reports (charity, medical), etc. My laptop is old and I need to get a new one which will have Windows 10 to which the Money 2006 is not compatible. Do you know of a program in the money style that operates for my “simple” taste. I don’t need budgeting or charts and grafts or the fancy stuff. It would be nice if the new program could incorporate (import?) my old files. Please email me the answer and withhold this from publication. I doubt there are many “antiques” like me out there who would be interested in this question.

 – Name and City Withheld.

A:  Let me start by repeating something that I’ve said in the past.  The purpose of this column is to get helpful technical information out to all of my readers.  I have no desire to do one-on-one free technical support via e-mail, and I respectfully disagree with you about whether people will be interested in your question.  That might be true if I strictly limited my response to Microsoft Money 2006. However, I see this as a question that is primarily about running older software under Windows 10.  Out of respect for your request, I’ve withheld your name.  However, I am going to answer the question for publication.

Now then, on the surface, this would seem to be a textbook example of why you should always keep your software updated.  However, that would ultimately be a losing proposition in this case, as Microsoft discontinued this particular product in 2008.  Not having a copy of Money 2006 to play with, I don’t really know the exact incompatibility problem you’re experiencing.  However, there are multiple facilities available to you that would allow you to run it in a compatible environment.

The first thing I would try is what Windows literally calls “Compatibility Mode”.  Find the executable file for the program (in your case, it’s probably named money.exe, but possibly not).  Follow the shortcut from the desktop or the Start menu to see what file it runs when you activate it.  Once you’ve found the executable, right-click on it and select “Properties”.  Go to the “Compatibility” tab.  Click the big button labeled “Run Compatibility Checker” and Windows will analyze the program for potential incompatibilities, and then launch into a wizard-like interface that will allow you to try running the program with compatibility selections, or perform guided troubleshooting.  Go through this process as many times as necessary.  Either you’ll get the software to work, or the troubleshooter will tell you with absolute certainty that the software can’t run under your version of Windows 10.

If the latter happens, you’re still not licked.  I refer you to an issue I wrote last year (Geek Note: I.G.T.M. #621, June 16, 2019), which you can read for free on my website.  This issue, and another issue to which it refers, describe methods of using what is called a virtual machine to actually run an older version of Windows underneath your current version, which then allows you to run your software in its preferred native environment. This is not very easy to set-up if you’ve never done it before, and it definitely helps to be a pretty geeky individual.  However, it is absolutely guaranteed compatibility, since your older software runs not under Windows 10, but rather under the actual older Windows version.

Before you walk that road, I did a little digging for you, and found that although Microsoft discontinued Money 2006, there exists a product called Money Plus Sunset Deluxe that might be exactly what you need.  Check it out at TinyUrl.com/IGTM-0662.