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)
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
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
start Mongrel server.

I realized that running an old RoR app with latest RoR related versions
I even tried RadRails IDE and set installed interpreters for Ruby, but
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
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

  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
installed in the old ruby/bin directory luckily.
I didn’t have to run rake gems:unpack command and I just copied ruby
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
Ruby on Windows is always…interesting!