Alternatively you can downgrade the gem system using 
$ gem update --system 1.4.2

If you are on a higher gem version, it downgrades it. 

As far as I know, 1.8.25 gem works well with Rails 2.1 onwards with Ruby 1.8.7 
and rake (0.8.7). 
I also think rack (1.1.0) causes problems as it's quite a later version. You 
may want to remove it or downgrade it to a version before 1.0

--
@gautamrege
~~~~~~~~~~~~~~~
All wiyht. Rho sritched mg kegtops awound?

On 06-Feb-2014, at 4:21 am, Matt Jones <[email protected]> wrote:

> 
> 
> On Tuesday, 4 February 2014 19:58:31 UTC-5, vgaiter4 wrote:
> Per a customers request I installed redmine 1.3.3 on Ubuntu 12.04.3 LTS. I 
> have followed the install instructions to the letter. However when I go to 
> launch the website Http://myserver/redmine, I get an error stating "the Ruby 
> on Rails application could not be started". Can some one please give som 
> insight on what I may be missing?
> Gems installed...
> Ruby 1.8.7
> Rails 2.3.14
> Rack 1.1.0
> RubyGems 1.8
> 
> 
> Some of the Rails 2.3 versions have problems with newer versions of Rubygems. 
> Try installing rubygems-update of an older version (`gem install 
> rubygems-update -v 1.4.2`) and running update-rubygems.
> 
> If that doesn't work, post the rest of the "Rails Application Failed To 
> Start" screen - there's usually a bunch of debugging info on that page.
> 
> --Matt Jones 
> 
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