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this post was submitted on 20 Jul 2026
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No Stupid Questions
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No such thing. Ask away!
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Well, old software doesn't run on windows anymore.
Not sure what you mean by old.
10 year old Windows software? Will definitely run.
20 year old Windows software? Will run but might require admin rights or compatibility mode.
30 year old Windows oftware? Might run but probably need a VM.
For Linux the focus is more on improvement, less on compatibility. That's a deliberate decision.
Not true.
It really depends. And I say this as someone who's spent years in the enterprise software management space.
In the last few years, older software has become less capable of running on Windows. Tried to run a 2006 app the other day and it won't even install. So had to run it in a VM of Windows 7.
But your general point still stands. Lots of SMBs can continue to run on older software, to a point.
I do still use LOTS of old software with little ussue.
What is the application you had issues with? It's very uncommon for a 10 year old application to not run on Windows. And if it doesn't, it's usually not the fault of the OS but of some obsolete technology.
Why do you need to run 10-30 year old software? This is a big red flag in my book: if your software can’t be bothered to be upgraded then why would you expect your OS to be?
What is the problem of running 10-30 year old desktop software locally? This is actually very common in some sectors, such as governmental infrastructure or industrial use. It's not like those applications are reachable from the internet or even contact a server. Windows itself ships with applications that haven't changed for decades, such as the character map and resource monitor.
Then run it on the relevant (outdated) OS? Why should the OS be constantly held back because the software sucks?
If the developer would just address the issues as they come and recompile for OS upgrades it shouldn’t be a problem — but if you’re using software where the developer can’t bother to recompile after 30(!!!) years I think there’s a more serious problem.
Ideally you want the OS to be updated, because old OS are vulnerable when the computer is networked. In fact most IT departements require every PC to have an up to date OS.
It's not always a matter of bothering - many applications are customized and made for a specific purpose. An application could have been sold to only one company as a one off, or even developed by a long retired employee. Want an update after 20 years? Sure, after paying another invoice, provided that the developing company still exists and is still willing to support such old tech.
It is just a given that many companies are stuck with some old software somewhere in their process. That explains the policy for Windows.
Windows: "if we stop shipping this 25 year old library 5% of corporate users will experience problems which will cost us money and reputational damage, so we keep it compatible."
Linux distro: "we are going to replace X with Y because it is better. Things will break and it is partially up to the community to solve it."
Sometimes software is just... Done. Feature complete and sometimes still just the best way of doing something. It's a rare thing, but sometimes happens.
I guess a good example is WordPerfect 6.2 for DOS; it's to this day a great WYSIWYG word processor, and the most feature complete TUI word processor for people who like distraction free writing. There are still proponents meticulously documenting how to get it working and integrated with modern OS's so that it can access modern printers.
Games comes to mind.