Moving an old rails app from windows 2003 server to windows 2008 server.


I have developed a small RoR app(ruby 1.8.6, rails 2.1.0, rubygem 0.9.4) a few years ago and I have not worked on RoR since.
Now, for some reasons, I need to move this RoR app(running on 2003 server currently) to new box which is windows 2008 server.

I copied the old RoR app in my local machine(windows 7) and I downloaded all the latest(using rails installer) in my local machine(windows 7) and tried to run the app, but I ran into all kinds of issues. I couldn’t even start Mongrel server.

I realized that running an old RoR app with latest RoR related versions is nightmare.
I even tried RadRails IDE and set installed interpreters for Ruby, but when I tried to start server, nothing happened…even nothing appears in the console.(both WEBrick and Mongrel)

My question is that what is the best/trouble-free way of moving an old RoR web to the new box?
Is it possible to copy all RoR related installations from the old box to new box and copy the app directory and run it from the new box?
It can’t be this much trouble…

thanks in advance

Hey Daniel,

As you’ve discovered, you’d have a fair amount of work to do to get the application to the latest version of Rails.

If you’re fine running totally old, crappy stuff (:D), then try the following:

  1. On the old box, use rake gems:unpack
  2. Copy the application directory to the new server
  3. Get Ruby 1.8.7 for Windows (it’s unsupported by mainline, but still seems to have a package)
  4. See if you can get the app working with WEBRICK
  5. If you can get it working with WEBRICK, then try Mongrel…
    I’m interested to see how you go!


Hi Timothy,

Thanks for your comment.
I followed your instruction and it looks like I have pretty much everything installed in the old ruby/bin directory luckily.
I didn’t have to run rake gems:unpack command and I just copied ruby dir, the application directory, oracle client and set and set everything in windows environment path and it worked with some config files changes.


Hey Daniel,

Glad to hear you got it working! Sounds like it wasn’t so bad in the end. Ruby on Windows is always…interesting!