win7-64 to win10 upgrade - what actually happens?

[peter-h]

I could not think of a better subsection to ask this.

I have a win7-64 PC which needs to be updated to win10, because 1 or 2 apps demand it (like the UK HMRC tax calculation software).

It seems clear that if I purchase win10 full retail, there should be an option to preserve apps and settings. Fair enough - it may work...

But what about old apps, from say 20 years ago. These are win32 apps (can't be win16 AIUI because win7-64 does not have the win16 support) so "should run" under win10. Can anyone offer any input on how well this works? There are conflicting views on whether win10 has an XP compatibility mode; some say no. I have almost never found any of the compatibility modes to do anything useful, however. These old apps are really XP-era apps which run fine under win7-64.

Of course there is the VMWARE route which I already use for old CAD etc apps (Protel, Orcad...) but it is an extra step.

Some old apps stored config data in c:\windows\win.ini and/or in the registry. Does this stuff get carried forward? IIRC, the last time Windows did an upgrade which tried to preserve apps and settings was win3.1 to winNT

Thank you for any input.

Please, no comments on lack of security, etc. The win7-64 machines are on a LAN, not exposed, and FWIW are updated to latest MS contract customer level using the Simplix route.

[radiolistener]

I don't recommend to update to windows later than win7, if some software don't works, just use VMWare VM to run it. If you want to update OS, then switch to Linux...

[DavidAlfa]

I'd use dual boot or XP/ 7 VM for those older apps. Software running in W7 but not on 10 is pretty rare, but could be. Usually all it needs is spoofing the windows version in compatibility settings.
AFAIK Upgrading to Win10 will keep everything, but you'll have a month to perform a rollback, so you'll be safe.
https://answers.microsoft.com/en-us/windows/forum/all/going-back-to-windows-7/f02e62cf-6b95-4a98-a9bc-247543912e7

[bte]

I have a win7-64 PC which needs to be updated to win10, because 1 or 2 apps demand it (like the UK HMRC tax calculation software).

Please, no comments on lack of security, etc. The win7-64 machines are on a LAN, not exposed, and FWIW are updated to latest MS contract customer level using the Simplix route.

So the tax software works fine without connectivity i.e. you enter data and it spits out the result and you take it to a connected machine to upload?

I keep a Windows 10 Virtualbox VM for such stuff (I do have an older -yet still powerful enough- machine upgraded to Windows 10 during the free offer in case a VM is not sufficient for whatever reason). I wouldn't upgrade the machine if I were you, at least not without making a full backup and restore to make sure that the backup is usable. Or you could clone the disk and run the upgrade on the cloned disk to see if all is well. If not, you can plug in the old disk and continue without any issues.

Win.ini is for 16-bit apps and I would be surprised if Windows 10 upgrade honors its contents or does anything with it. Anything in registry should transfer as-is since only Windows 10-specific modifications would be done during upgrade.

Does the machine have drivers (i.e. display, chipset etc) for Windows 10?

As a side note, I don't think you can purchase Windows 10 retail licenses anymore (at least not digitally) but a Windows 11 key should work fine in activating a Windows 10 machine.

[peter-h]

So the tax software works fine without connectivity i.e. you enter data and it spits out the result and you take it to a connected machine to upload?

Yes you can do that. The payment is done via another process.

I keep a Windows 10 Virtualbox VM for such stuff

I have a win10 VMWARE VM, which runs under the win7-64 OS player, but it is extremely slow for some reason. I might do that.

I don't think you can purchase Windows 10 retail licenses anymore

You can on Ebay. They have all been withdrawn on Amazon, amusingly

On an amusing point: the UK HMRC employee tax calculation software can update itself and when it does, after about Feb 2025, and finds it is under win7, not win10+, it quietly destroys itself. It seems to be written in Python (various .py modules and related error messages). The only way out is to install a fresh copy under win10 and transfer the old backups (stored on a very long and by default "hidden" path under \users).

[bte]

I don't think you can purchase Windows 10 retail licenses anymore

You can on Ebay. They have all been withdrawn on Amazon, amusingly

That is why I said

As a side note, I don't think you can purchase Windows 10 retail licenses anymore (at least not digitally)

because Microsoft stops selling the older OS once the new one ships. Probably it also has agreements with Amazon etc to not offer the old ones as well.

I know Ebay et al will be a source of "licenses" but most of them will not be legit. I took a glance at what is available and very few made the claims of being a brand-new, shrink-wrapped product that would hopefully activate fine. If you need to be properly licensed, I would suggest getting a Windows 11 license from Microsoft and activate your copy of Windows 10 with that. If proper licensing is not a requirement, then there's no need to spend any money on the items offered on Ebay. The activation script on github will work wonders with most (all?) of your MS activation needs. Since it's a script, you could check what it is doing so no virus etc. I think there's even a lengthy documentation about how various aspects of it works.

[peter-h]

I see a number for around 30 quid
https://www.ebay.co.uk/sch/i.html?_nkw=windows+10+full+retail&_sacat=0&_from=R40&_trksid=p4432023.m570.l1313

Rarely had a problem and if I had, I ask the seller and he gives me a real product key

BTW would anyone know why a VMWARE win10 VM should run very slowly under the win7-64 host player? It is usable but only barely.

[thm_w]

Backup HDD.
Upgrade and see what happens.

Most of us had no issues but who knows what might happen.
Apparently the free 7 to 10 upgrades ended in 2023.

[Shock]

I suggest buying a new SSD. Installing whatever OS you intend to run clean. Install the apps, opting for the latest version if possible keeping a copy of the installers used. Copy the data over and test everything including peripherals. Keep the old drive and data as one of the backups should you run into problems.

If you cannot get certain apps to run under that version then you can try imaging your old windows installation into a vm or even better make a fresh vm and install any old apps clean and copy in the data.

Doing in-place migrations is incredibly sloppy and mostly done by people who don't know any better.

Edit:
This achieves latest OS updates and support and you're not even bound to Windows anymore for your host OS. An almost guarantee all apps will still have facility to run, a better performance outcome, a chance to change to the latest version of individual apps if possible but not be bound to them. A recovery or wayback option in a worst case scenario.

[nctnico]

I'd run the tax software on Linux. I assume they are not that daft to provide a Windows only version nowadays.

[mikeselectricstuff]

If it's just a couple of apps that aren't in regular use,  and aren't power hungry, then running just those on a £50-£100 Win10 laptop from Ebay might be a quicker & easier solution

[peter-h]

That's exactly what I did to test the OS dependency.

[Jeroen3]

Some old apps stored config data in c:\windows\win.ini and/or in the registry. Does this stuff get carried forward? IIRC, the last time Windows did an upgrade which tried to preserve apps and settings was win3.1 to winNT

Apps are not supposed to store stuff there. The installer may put drivers in there, but not much more.
During the upgrade any incompatible drivers will be removed. As in, all unsigned drivers will be removed.

All apps and stuff will remain in place, basically only the current Windows folder will be moved to Windows.old and a new one will be installed.
The windows.old folder can be removed by disk cleanup. It's owned by system, so you can't delete it.

Make a disk image and try it. If you don't like it you can go back. (You could even go back with shadow copies iirc)

Of course, if apps change their behaviour during install based on the version they are installed on, you're out of luck.
But apps that don't work can often be repaired using the installer. Decent stuff has this option.

I haven't really encountered anything that stopped working, except drivers and niche stuff that worked around the api's regardless. Like game engines.
(windows 10 has different kernel timings)

[Smokey]

Boot a linux usb drive (it is new enough to have a USB port right??) and dd your entire machine into a disk image.  Then scrap that whole computer and run it moving forward as a virtual machine (preferably with no internet access) if you have to keep it going.  The machine probably won't even know it's no longer a real computer, and you can play with stuff like upgrading to another soon-to-be-unsupported OS without worrying about losing anything.

There appear to be a lot of you guys running old versions of windows on your daily driver computer.  You are all sort of crazy.  If you need some arcane program, and others have mentioned, there are better ways to do that than just never upgrading anything and being constantly infected by everything on the internet.

[peter-h]

being constantly infected by everything on the internet.

That FUD is all over the internet and everybody repeats it. It's completely false - unless one is visiting p0rn sites and such. Behind NAT, your computer is inaccessible, except via obscure means (which generally need inside information) and only during the brief times it goes online.

The reason for running old apps is to protect investment in time and money. For apps which need XP or earlier I use an XP VM and that works fine.

In this case we have a crappily written app which blows itself up during an auto update if it discovers the OS is below win10 Today I will set up a win10 VM and test it. IME win10 VMs (on a win7 host, running the last VMWARE player on win7-64) are very slow but this app gets run only once a month. What I could not really run on that win10 VM was Cube IDE - it was realy painful.

Apps are not supposed to store stuff there

A lot of XP-level apps do use win.ini. It was normal 20 years ago. AFAIK no win7 apps do.

But this in itself should not be a problem. Win.ini lives on in c:\windows and old apps are free to keep stuff there. More tricky are path changes e.g. the Program Files (x86) mess which win7-64 brought in.

[stretchyman]

Upgrading to a new win OS usually leaves a bit of a mess and far better to do a clean install.

Simple enuf to dual boot or even simpler to use another PC.

I have a WIN7 PC running older software which I access via remote desktop.

You have a lot of choice!

Str.

[PlainName]

On an amusing point: the UK HMRC employee tax calculation software can update itself and when it does, after about Feb 2025, and finds it is under win7, not win10+, it quietly destroys itself. It seems to be written in Python (various .py modules and related error messages). The only way out is to install a fresh copy under win10 and transfer the old backups (stored on a very long and by default "hidden" path under \users).

For Python you could try VxKex NEXT which spoofs W10 enough to let Python work. (This is the easy fix to getting Kicad 9 working on W7.)

However, if you're going to W10 then I would suggest you take the opportunity to start with a clean install rather than migrating if for no other reason that it clears out all the crud accumulated over the years. Stuff gets installed and uninstalled, but leaves a mess behind, for instance. The registry just keeps getting bigger without limit, etc. IME, going that route means a week or so of installing (and, just as important, importing saved settings) stuff you know you want, then a month or two of the odd dregs being remembered.

Another important aspect is that when I do this I typically upgrade to a new machine, so the old one is still around if necessary (though usually only to pull off settings or data). After it's not been used for a bit the machine is repurposed and any later access is via mounting of the last backup image.

[peter-h]

Currently I am running a win10 VMWARE VM for this one program

That is an amazing program - to spoof win10. IMHO you could make 99% of such programs work just by returning the win10 OS version; almost nothing uses any different OS API calls.

[mikeselectricstuff]

Currently I am running a win10 VMWARE VM for this one program

That is an amazing program - to spoof win10. IMHO you could make 99% of such programs work just by returning the win10 OS version; almost nothing uses any different OS API calls.

Wonder if there is a utility to just do that without needing   VM?

[PlainName]

Currently I am running a win10 VMWARE VM for this one program

That is an amazing program - to spoof win10. IMHO you could make 99% of such programs work just by returning the win10 OS version; almost nothing uses any different OS API calls.

Wonder if there is a utility to just do that without needing   VM?

VxKex NEXT

It's not an app or VM. You enable it for an app in the same way you would set compatibility mode, and it then tells the registry that the low level system DLL it's been calling is not the one it should for this app (kind of, E&OE). Not perfect but when it works it's better than moving to W10.

[coromonadalix]

never experienced problems on "old softs" who where used under Xp or 7,  in Win 10 Win 11 ?

even under x64,  you can run some 16 bits apps with ntvdm ... had to do it to run old pre-pentium / pentium coded era stuff, even some basic compiled exe's

VM are one way to go, just crank up the physical memory if you can,  to help ...  redirecting lan usb or serial is relatively easy for external devices


sure some exe's,  call windows version cvore or id's and stall when seeing an higher than needed one ... and sadly a vm is needed

[PlainName]

VM are one way to go

But not a good one because it's isolated from the host. So all those utilities that make life smooth, such as Listary, don't work on whatever is in the VM. Takes forever to start up too, so either you run the VM all the time (even when not using the app in it) and basically make unusable the resources it takes, or you put up with long load times of the app. That last is a killer because  there will be times you would normally just fire it up for a quick check of something, but now you won't. Maybe you just want to verify that mounting hole was moved half a mm... oh, sod it, it's probably OK.

[elektryk]

Some weird programs can detect VM and refuse to work...

[peter-h]

VxKex NEXT

I am not familiar with that site. Is there a windows executable or install package somewhere?

Some weird programs can detect VM and refuse to work

Sure they could but I haven't seen one yet. Surprising perhaps, given how great VMs are for busting copyright and licensing restrictions, etc.

Takes forever to start up too, so either you run the VM all the time

VMs are pig-slow for win7 guest, and higher. WinXP guests are very fast. A win10 guest is barely usable but it is OK for an app used once a month only.

[elektryk]

VMs are pig-slow for win7 guest, and higher. WinXP guests are very fast. A win10 guest is barely usable but it is OK for an app used once a month only.

W7 host with W7 guest and Debian guest was quite ok (i7 4gen, SSD).
The same with W10 host and W11 guest (i5 3gen, SSD).