Trying to upgrade an XP machine to upgrade to Vista

I know - what the heck am I upgrading to Vista for?!  Well I need to "leap frog" this machine to Windows 7, if I possibly can.  there are a lot of special configurations on this old XP box that I want to try and preserve, and do not want to have to rebuild.  I know its a long shot - and I know its never recommended to do the upgrade path.  But if it works, it will save a lot time and effort.  Ofcourse - at what point am I spending more time and effort upgrading it, right?  That's why I wanted to check with some experts to see if theres any help for what I'm experiencing.  So I've got a 32-bit XP SP2 machine, and I'm attempting a Vista Business SP1 upgrade.  It gets to the compatibility phase, and after "checking compatibility" for 5 minutes, it results with an empty compatibility window and a CLOSE button - which cancels the upgrade.  I'm guessing theres an application or driver that's incompatible and stopping the upgrade - but its not telling me what it is.  I then tried running Vista and Win 7 upgrade advisors, and those won't run for some reason. seems I'm stuck.  Any ideas out there?

Thanks for your help.
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Gary CaseConnect With a Mentor RetiredCommented:
One other key point r.e. using a virtual machine:   You don't have to worry about OS compatibilities ... you may find that some of your older programs won't run on Vista or '7  => although I've found over the years that MOST of the time when folks say a program won't run it's because they're trying to run an x32 program in a x64 OS.    MANY programs that folks tried to move from XP to Windows 7 and said they "wouldn't run" will actually run just fine in Windows 7 x32 ... just not in the x64 version.

But if you spend the time to virtualize the XP system you'll have several advantages:

(1)  There's no question r.e. compatibility, since you'll still be running XP.
(2)  You'll be able to move that VM to ANY new computer you might get by simply installing a hypervisor.    [This is a key reason I suggest using VMWare, as you don't have to restrict yourself to versions of Windows that support Hyper-V]
(3)  "Backing up" your XP system is as simple as shutting down the VM and then just copying the virtual hard drive to a backup location [I'd actually copy the entire folder containing the VM, which has a few additional configuration files]

It will likely take you less time to move to a virtualized system than it would to do the "leap frog" updates you're thinking about; and it will be FAR more reliable and maintainable => and if you run it on a reasonably modern system it will probably even "boot" faster :-)    [My virtualized XP systems boot in  ~ 15 seconds on an i7-4770]
Scott SilvaConnect With a Mentor Network AdministratorCommented:
I assume you most likely need XP service pack 3 before you can even try...
KaffiendConnect With a Mentor Commented:
Virtualize it....

(And use whatever hardware firewall you have to severely restrict this vm)
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Check which ports are open to the outside world. Helps make sure that your firewall rules are working as intended.

One of a set of tools we are providing to everyone as a way of saying thank you for being a part of the community.

Scott SilvaNetwork AdministratorCommented:
also. If you happen to have XP Media Center edition your only upgrade path is Vista Ultimate
Dave BaldwinConnect With a Mentor Fixer of ProblemsCommented:
You also need a 100% bootable backup before you try this again.  I don't think you are likely to succeed with this upgrade in any case and you must be able to put the machine back the way it was.
Gary PattersonConnect With a Mentor VP Technology / Senior Consultant Commented:
First of all, forget the intermediate Vista upgrade.  Go from XP to Win 7 (after getting a good backup of course).

1) Uninstall the Win 7 Upgrade Advisor and then reinstall and run as administrator - or better yet activate the local Administrator account and log in and run the advisor while logged in as Administrator.

2) In this thread, several people describe an old uninstalled version of McAfee AV caused Advisor  and upgrade problems:
John HurstConnect With a Mentor Business Consultant (Owner)Commented:
Also you have a 32-bit operating system. 32-bit is as dead as XP. If the computer is a 64-bit computer (look in Device Manager under the CPU) then go directly to Windows 7 64-bit.

If not 64-bit, time for a new Windows 10 64-bit machine.

Even now, upgrading to a starting point of Windows 7 is not a good idea. You want to move on to Windows 10 and be done with it.
Gary CaseConnect With a Mentor RetiredCommented:
"...  there are a lot of special configurations on this old XP box that I want to try and preserve, and do not want to have to rebuild.: =>  I suspect the time to rebuild your configurations isn't much more than the time you'll likely spend trying to upgrade this without losing them.

However, if you really want to retain the XP configuration, I'd download VMWare's P2V tool (physical - to - virtual) and create a virtual machine from your XP system.    Then you can run that virtual machine on ANY hardware that you install VMWare's free VMWare Player on and it will run fine ... no upgrade worries as you move to newer machines.

If you really want to try upgrading the physical machine, the earlier suggestion that you need to install SP3 is right on-the-money.    That service pack was required to do an in-place upgrade to Vista.     And as I suspect you know, once you do the upgrade to Vista, you can then upgrade that to Windows 7.    I suspect that's the path you're trying to follow -- but I think the virtualization approach is a far better choice.   An XP VM on newer hardware will likely boot faster than XP on older hardware; and you'll be completely independent of the actual hardware going forward.
nobusConnect With a Mentor Commented:
since your Original system has a lot of value for you, i suggest to take another disk drive (bigger size?) and image your drive to it
then you can work on the image, without fear of loosing your Original setup

upgrading to win 7 or win 10 may be possible or not (driver problems) depending on the system model
Mike TConnect With a Mentor Leading EngineerCommented:

I'd go with what Gary said! Yes, I mean go virtual. VMware's P2V is good but I've also had great success with Disk2Vhd.exe (a free sysinternals tool). You would then need a machine with Hyper-V on and create a new VM and attach the VHD as the boot disk. Job done.

The amount of time you spend running P2V and installing a hypervisor (VMware or MS) will be a few hours.

OS leapfrog is never, ever as much fun as the real thing.
John HurstBusiness Consultant (Owner)Commented:
I think you (asker) should consider getting a decent Windows 10 Pro 64-bit machine, then VMware Workstation or Player and make an XP Virtual machine as some suggested here. I do this and have a couple of XP machines for different purposes.
Damian_GardnerAuthor Commented:
sorry for the delay gentlemen.  I have a ton of feedback here - which I am grateful!  I'll need to weed thru it here and figure out my best course of action.  I appreciate all the input and will report back soon on this to close out the thread.

Thanks to everyone.
Damian_GardnerAuthor Commented:
Let me ask everybody here - should I be worried about security holes and malware attacks, even when I virtualize the XP system?  This was the main reason we've been upgrading all of the remaining XP systems.
John HurstBusiness Consultant (Owner)Commented:
XP is full of holes and because it is dead, the holes will not be fixed. There are holes in every system but newer ones continue to be patched.

It does not matter virtual or real.
Put that puppy in a DMZ-like environment (restrict traffic in or out to only what is absolutely necessary) if you can - at the very least, stop it from going out on to the internet
Gary PattersonVP Technology / Senior Consultant Commented:
XP went to "end of life" (EOL) on April 8, 2014.  That means no more fixes, no more security patches, no more service packs, and no support from Microsoft.

There are multiple known security vulnerabilities in XP that have been discovered since the EOL date.  

Continuing to run XP in your network can cause you to fail to meet a variety of security standards, or require you to implement expensive compensating controls.  Here's a FAQ related to PCI DSS, for example:
Damian_GardnerAuthor Commented:
I thought as much.  Thanks for weighing in gentlemen.  I am considering just going thru the pains of rebuilding the machine from the ground up on a new Windows 10 machine.  Thanks for everyone's input on this.
Gary CaseRetiredCommented:
"... should I be worried about security holes and malware attacks, even when I virtualize the XP system?  " => This really depends on just what you're using the machine for.    If it's only running on your local network and you never access the internet, it's fine.   You simply disable automatic updates (no reason to have them on anyway, since there are no new XP patches); and don't ever run a browser.

In addition, since it's a VM, it's completely isolated from your "real" machine (the host), so it can't do any harm to that.    You can also very trivially image/restore the system by simply copying the virtual hard drive.
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