Playing DOS games on your iPad

Space Quest 1
Civilization
Wing Commander

These are the dominant games of my youth.  I may have played 100 other games, but these two sit in my conscious as games I will never be able to forget.

Twenty-plus years later, I find myself with a 40 minute train ride looking for things to fill the time.  I've never been a big TV watcher and today's mobile games just don't connect with me in the same way (even the newer remakes, like Civilization Revolution just don't scratch that same itch).  So I got to thinking - the iPad is a very nicely powerful device (at least in the context of twenty year old games) - why can't I play my favorite old DOS games on my iPad?

A couple years ago, Apple allowed (very briefly) a DOS emulator called "iDOS" onto the App Store and then promptly yanked it.  Another update followed and again, released and yanked.  So, within the "walled garden" of the App Store, there is currently no way to play these old DOS-based games.  Which means, if you want to do these kinds of things on your iPad, you're heading into the world of jailbreaking.

For whatever reason, I've always been afraid of jailbreaking my device.  I figured there's a chance I would "brick" the device and be out $500.  I also thought it was illegal.  Both of those, I am happy to report, are myths.

The process of jailbreaking your iPad is relatively painless.  I used the rather provacatively titled "Absinthe" program to jailbreak my iPad (http://www.iphonehacks.com/download-absinthe).  While it took a good 20 minutes and it ended up clearing off all my side-loaded content (movies, ebooks), it worked on my iPad (WiFi 16BG first generation) and flawlessly at that.  So good on them for having a nice tight process.

That's where the "clean and easy" part of the story stops.  The rest is quite frankly not for the faint of heart.  If you like the "no mess" aspect of Apple installs from the App Store, well buckle up that chin strap because this is going to be a rough ride.  I've had a fair amount of experience monkeying around with installs in the old DOS days and am glad that part of the user experience has been eliminated.  If you're totally new to this, my condolences - it can be unpleasant but it's worth it.

So theoretically, you go into Cydia on your iPad (this is a new app post jailbreak, basically an App Store for jailbreak apps), choose "Sections" along the bottom (Cydia is known for re-arranging its interface so these instructions may not work a year from now), choose "Games", and find "DosPad Beta 1.92".  Choose "Install" at top right.  If you're lucky, you now have a "DOSPad" icon on your home screen.  I was not.  I got a "size mismatch" error and after a couple of hours of googling through possible solves, I finally landed on the legacy DOSPad support page (yes there are two, just for funsies) : http://litchie.com/apps/dospad.html  The support page says that if you can't install via Cydia, you should "manually" install the "deb file".  If your head is spinning, so was mine.

In order to manually install the app, I used the following walkthrough : http://ipad-os.net/how-to-install-deb-file/  Just to make things a bit more fun, they include four (4!!) different ways to do a manual install.  I'll just save you the pain and tell you I used #3 (iFunBox) and it worked just fine.  I did end up installing "iFile" on my iPad but I never needed it.  Plus iFile starts down a path of opening your iPad's security and I did not want to deal with that.  So the short version of the install goes like this :

1. Jailbreak your device
2. Install iFunBox on your PC (http://www.i-funbox.com)
3. Connect your iPad to your PC
4. Open iFunBox and navigate to var/root/Media/Cydia/AutoInstall (create the folder if not there)
5. Copy the DOSPad deb file (http://code.google.com/p/dospad/downloads/detail?name=DosPad-Beta-1.92.deb&can=2&q=) to AutoInstall 
6. Reboot your iPad (hold top button, power off, press top button again)

You should now have a DOSPad icon somewhere on one of your iPad home screens.  If you've made it this far, congrats!  Because that's as hard as it gets although we do have to do more of this coming up.  Also, if you didn't need iFunBox to install, download it anyways because you will need it.

I can't remember whether DOSPad set up the folder or I did, but in iFunBox (again with iPad connected to PC and iFunBox downloaded, installed and open) you navigate to var\mobile\Documents and either there may be a folder called "Games" - again I can't remember if I set that up or not.  var\mobile\Documents is also the "C:" drive of DOSPad so keep that tucked away in the back of your head.

Copy your games from your PC to DOSPad's "Games" directory.  I had the Space Quest Collector's Edition already installed on my machine (that is it's own fun mess - see this link for more help : http://www.sierrahelp.com/Patches-Updates/NewSierraInstallers.html) so I just copied all of those already installed folders into var\mobile\Documents\Games in iFunBox.  As far as I can remember I think I just dragged the folders from Windows Explorer into iFunBox and it worked fine.  Space Quest 5 took a while to copy but whatever.  It worked.

For Civ, I just copied the "Civ1" folder in the same directory.

Here's where I hit another snag.  I disconnect the iPad (hit the eject button on iFunBox), I start up DOSPad, I enter "cd games\civ1" and then "civ".  The game loads up beautifully and I start playing but I can't save.  This is where Windows 7 drives me bananas.  For some crazy reason, when it copied the folder to the iPad, it marked it "read-only".  There are a couple of different ways described on various forums to fix this on the iPad (using iFile or iFunBox) - none of those worked for me.  I had to go back to Windows 7, right click on all the games folders, click properties, un-check "Read Only", click Apply and re-copy all the folders to the iPad.

Once I had done that, everything worked.  

One final note - iPad 1 is really short on memory.  If you use DOSPad and then try to access another app and try to get back to your game, you may find that DOSPad didn't save your game and you are back to the C: prompt.  Don't say I didn't warn you.

One more thing that is kind of fun to play with - once you've been playing Civ on your iPad away from your PC, you can use iFunBox to copy the save file back to your PC and pick up your game right where you left off.

I hope this write up is helpful for someone out there because I literally spent a week trying to figure all this out and I found that much of the support out there hadn't run into the same issues that I had.  It was a real pain and I nearly gave up on several occasions.  Hopefully you will have better luck.  But leave a comment if not and we'll figure it out together.