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I have to migrate a legacy Visual Basic 5 program from an old Win98 box to a Win 2008 Server. The installer of the program isn't available (it's a custom program).

I begin installing the VB 5.0 runtimes and copying the entire program folder to the new box, but it doesn't work (I suppose several DLLs and ActiveX controls are missing, so the program runs but bombs with different runtime errors).

I'm thinking of capturing all the program accesses to the filesystem and registry with SysInternals FileMon and RegMon, and making a program that copies this files/registry settings to the new box, but I'm afraid that this can be a hard work with uncertain results after all.

I looked for several programs that can create portable installations (Cameyo, ThinApp), but usually these programs a) requires an installer available and b) cannot run on Win98, where the program is running right now.

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Its a windows 98 box - why not just virtualise the WHOLE system to start with? You know for a fact that it'll work. While you probably can't just use a P2V tool, you could image the box, and image it back into a VM, and you'll be certain its an identical environment.

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Yeah, I think of virtualising the entire Windows with VirtualBox, but the program has to run concurrently on several computers sharing data, and it's used several times in a day: I don't think that's practical for my customer to start a VM any time that he want to run the program. Also, I'm not sure the program file sharing works fine on a networking environment running from inside the VM. I'll keep this option as a last resort, thanks –  PabloG May 2 '11 at 0:23

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