Upgrading Windows Vista 32 bit to 64 bit Windows Server

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I am planning on upgrading Windows Vista Home Premium 32 bit to Windows Server 2008 Standard 64-bit (I have a quad core cpu which supports 64 bit and I have 4gb memory so can’t see all of it at the moment).

My concern is, some of the development software I have (like those made by the smaller vendors) will not work in this new environment.

The consensus is that my existing apps will work as long as they are 32 bit and not 16 bit, but how can I find out whether they are 32 or 16 bit? I don’t want to email each vendor. What are my options if they are 16 bit – host in terminal services?



Almost all software written in the last 10 years is 32-bit (or greater) – I would say “all”, but I’ve learned not to do this on SuperUser. I wouldn’t worry too much about this if you have purchased your development software in this decade.

If not, you can always host your 16 bit software within a virtual machine.

You can find out whether an application is 16 bit in various ways:

  • Look at them.
    • If they don’t use visual styles it might be, but many 32-bit applications also do not.
    • If the console window resizes itself to 80×25 (indicates command.com starting) then it’s definitely one.
  • Look elsewhere
    • The task manager will have a process named ntvdm running. This is the Windows NT Virtual DOS Machine, i. e. a host process for 16-bit legacy stuff.
    • Do file open dialogs look like the “Add fonts” dialog in older versions of Windows? Do they only show 8.3 file names?

There are a few ways. Looking for ntvdm is the most reliable one.

That being said, there aren’t many 16-bit applications still in use. At least not outside very specialized areas.

If I was you, I would just go with the upgrade and simply run any old program in Virtual PC or another virtualisation program

Straight from Microsoft:

Learn How to Spot a 16-Bit Application

Because most Windows 3.x–based
programs run properly under Windows
XP, it’s sometimes difficult to tell
16-bit and 32-bit applications apart.

Here are two methods for determining
whether an application is 16-bit or
32-bit: •

Right-click the program’s executable
file and then choose Properties. If
you see a Version tab, it’s a 32-bit
program. •

Or, if the program is running, press
Ctrl+Shift+Esc to open the Windows
Task Manager. On the Processes tab,
look in the Image Name column for the
name of the program’s executable file.
If any 16-bit programs are running,
you’ll find an entry for Ntvdm.exe,
the virtual DOS machine. Just above it
in the list, you’ll see indented
entries for Wowexec.exe (the Windows
on Windows subsystem) and the
executable name of each 16-bit program
running in that virtual machine.