Make sure you have two processes running after :Rdebugger command:

• rdebug-ide
• ruby ruby_debugger.rb

Please, show output of all files in ~/.vim/tmp directory.

When I run :Rdebugger first time it starts two processes, but after a few seconds one of them shuts down. I can't tell wich one of them is ruby_debugger, but the one that keeps running has multiple ports open (39768, 39767, 56590).

When I run :Rdebugger second time both processes keep running. The new one has only one port open (39767).

ruby_debugger file contains this string http://gist.github.com/118463
There are two more files – ruby_debugger_log and ruby_debugger_output – but they are empty.

Hmm... could you make sure what process exactly shuts down? It can help.
Meanwhile, I'll try to debug Sinatra on my local desktop.

The one with one open port.

Looks like it doesn't work for me too. :(
Please, try to set breakpoint to some first string (e.g., to require 'sinatra') before :Rdebugger command. And then, execute :Rdebugger. It should stop on this breakpoint. (as for me, the debugger behaves this way).

But after this, if I press 'continue', it will not run the server. Strange... Maybe problem in the ruby-debug-ide gem. I'll try to debug manually, by this gem.

I've tried to debug it manually. I run:

[anton@localhost sinatra]$ rdebug-ide -p 39767 -- sinatra_app.rb
Fast Debugger (ruby-debug-ide 0.4.5) listens on localhost:39767

And in other console, run irb and execute:

[anton@localhost sinatra]$ irb
irb(main):001:0> require 'socket'
=> true
irb(main):002:0> a = TCPSocket.open('localhost', 39767)
=> #
irb(main):003:0> a.puts('start')

After this, rdebug-ide just completed its work. Sinatra didn't run the server.

So at least we know the reason why it doesn't stop at breakpoints. It simply never runs.

Yeah... But if you want, you can set breakpoint to 'require 'sinatra'', run :Rdebugger, and try to understand why server doesn't start. Or just to make sure that debugger is working. :)

Really, pretty strange. Unfortunately, I don't have experience with workling/starling, never used them with/without debugger. I even don't know how I can help you, sorry...

If you find reason of this strange behaviour, I'll be happy if you send me patch, or just explanation of this bug :). Anyway, thanks for this issue, I'll leave it here unclosed.

Hi!
Please send contents of log files (in vimfiles/tmp directory).

I am not a skilled vim developer, but I tried to debug it and figure out that the script is doing something recursively then trying to execute:
let self.debugger_pid = self._get_pid(self.debugger_port, 1)

Ah! It means ruby_debugger.rb is not started by some reason. Could you try to run it manually? For this, put after

       " Start in background
       if has("win32") || has("win64")
          silent exe '! start ' . rdebug
          let debugger = 'ruby "' . expand(self.runtime_dir . "/bin/ruby_debugger.rb") . '"' . debugger_parameters

this string:

     echo(debugger)

Then, please show this command (result of echo) and try to run it manually. And then, tell me what you've got. :)

Seems I guess where the problem is:
I put the ruby debugger files to: %VIM%\vimfiles but not to %USER%\vimfiles

That is why the plugin didn't locate debugger ruby script