I have no trouble, with my installation of WINE, with navigating to my Windows XP partition, right-clicking on a Windows executable and "opening" it with WINE. Okay, so sometimes the file won't run (at least not straight up like that), but it works on some things.

I installed Ubuntu 12.04 on a friend's laptop at the weekend (creating a dual-boot system), because he uses Vista and is fed up with how slow it has become. Having done the basic installing of the updates and the restricted-extras etc, I installed WINE for him because he had a few apps in Windows that he could not do without. At some stage, we'll look at installing Photoshop properly in WINE.

However, I tried to show him that WINE could sometimes run Windows programs straight from the .exe file, and found a small program that I run using Wine on my Ubuntu 11.04. Unfortunately, on running it, WINE started up but after a few seconds gave up. I could not get any .exe files stored on his Windows partition to run using WINE. The Notepad supplied as part of the Wine setup (stored on the Linux partition) ran fine.

Can anyone think of any reason why WINE won't run, on a particular system, an exe file like this? I know some Windows apps just refuse to run on WINE - but I know that this particular app (a simple Youtube movie downloader) should, because I run it on my WINE installation.

Thank you for any help you can give.

(I am posting this query here, rather than on WINE's own forums, as I have never got a substantive response to queries posted there. I get much better customer satisfaction at LQ!)

Running programs from an installed Windows is never the way to go. Wine will not be able to find necessary dependencies, like Visual-C runtimes and stuff. Always make a clean install of programs you want to use.

Since you give us little information about the program and the involved OSes it is only guessing that can be done from us. May be the Vista installation is a 64 bit system, but you used 32 bit Ubuntu? May be there are libraries installed in XP in the applications directory that aren't there in Vista/7 because the OS already comes with them. May be you have installed a necessary dependenciy on your Linux installation that is missing on the new one.
But as stated, without more information just guessing and anyways not the way to do it. By the way, there are Youtube downloaders available for Linux (and also OS agnostic browser-plugins), so no need to use Wine for that.

Well I did go round there again last night and his Wine did run a couple of Windows executables (though not very well), so as you recommend I will install any Windows apps on Wine from scratch properly, using their installation files.

I do not know whether the Vista running on his system is 64-bit or 32-bit, as I know very little about Vista or how it works. I know his Ubuntu 12.04 is 32-bit.

I was perplexed why the Wine in my earlier edition of Ubuntu (11.04) could run these executables "on the fly" without installing, but the same ones did not run at all on his Ubuntu 12.04 Wine installation. But as you say, there could be many reasons why this is the case so it is like comparing chalk and cheese.

Thank you for your advice.