Over the course of the three weeks I have been using Ubuntu so far for the 30 Days With Ubuntu Linux series, there have been sporadic comments suggesting that I just run this app or that app in a virtual Windows environment from within Ubuntu. So, today I am taking a look at Wine.

Wine has been around for 17 years. It started as an acronym for WINdows Emulator, but the software evolved from an emulator to a compatibility layer, and the acronym was eventually adapted to be Wine Is Not an Emulator. Now, Wine is just accepted as the name of the software for the most part without regard for turning it into an acronym at all.

I will say that--on some level--running Windows software seems like cheating. It's like saying that an SUV is obviously a better vehicle than a Prius, but then towing a Prius around for those occasions where the SUV is too big or consumes too much gas to be practical. It's like deciding to be a vegetarian, and then spending all of your time trying to figure out how to make tofu look and taste like the meat you chose to give up.

To be fair, though, it is nice to have a tool like Wine available in your back pocket for special occasions. It is preferable to visit the Ubuntu Software Center and find native Linux alternatives to the programs you use(d) in Windows, but if there is software that you just have to run, and you can't find a suitable substitute, you can give Wine a whirl.

I opened up my handy-dandy Ubuntu Software Center and typed Wine in the search field, and...WTF? There are 14 matching items that show up. Many of them are variations on 'Microsoft Windows Compatibility Layer'. One has '(meta package)' at the end, another has '(dummy package)'. They each have a little sub-title like 'wine', or 'wine-gecko', or 'wine1.3-gecko'. Why isn't there just a single app clearly called 'Wine'?

I didn't really have any clue which of these various software packages is the real Wine, but the one at the top--the 'meta package'--had the most ratings and ranked highly at 4.5 stars, so I decided to give that one a shot.

Once it completed installing, I went to the Applications lens on the Unity bar and typed in Wine. It claims I have three apps installed that fit that description: Configure Wine, Uninstall Wine Software, and Winetricks. I was hoping to actually run Wine, but given these three options it seems that Configure Wine is the logical first choice.

I clicked Configure Wine and the Wine Configuration console popped up (go figure). At the bottom of the Applications tab, it specific which version of Windows to emulate...I mean be compatible with. It defaults to Windows XP, but I changed it to Windows 7. You can specify the version of Windows use on a per-application basis, and choose pretty much any version of Windows going back to Windows 2.0--although I can't imagine why you would want to do that. I applied my change to the Windows version, but left everything else on the defaults for now after poking around to see what the options were.

OK. Now, I am ready to run some Windows software, right? Let's get cookin'. I opened up the folder from my Windows drive where I store downloaded software, right-clicked my Microsoft Office 2010 installation executable and clicked 'Open With Wine Windows Program Loader', and...got an error message. Something to the effect that this software is not marked as executable.

I checked with Google, and found a helpful walk-through from Psychocats.net called Using Wine on Ubuntu. Apparently, the fact that the software is an EXE is not obvious enough, so I have to first right-click the file, go into the Properties, and click a checkbox designating the file as executable.

Seems convoluted. The problem is, every time I click the checkbox my check disappears. It won't let me make my file executable. I tried looking for more help on Google to no avail. I tried a couple other executable installation files, but couldn't mark those as executable either. I assume it is a permissions thing--like I need to somehow access the file permissions with root privileges in order to be able to make those changes. That is just a theory, though.

So, no Windows software running for me just yet. I expect to get some helpful advice and guidance in the comments to this post to point me in the right direction. By this time tomorrow, I should be doing more Wine and less whine.

Keep in mind that by running binary code meant for Windows within the Linux OS, you are potentially exposing the system to malware exploits it would otherwise not be impacted by. The relative risk is still probably lower than on Windows for a variety of reasons, but it is higher than an equivalent Linux system that isn't running Windows software in Wine.

Read the last "30 Days" Series: 30 Days with Google Docs

Day 22: Spread Out and Get Comfortable