I'm using:

Windows 7 64-bit Ultimate
Visual Studio 2008 Express Edition
Windows SDK 7

On this system, I couldn't get the Netbeans 6.8 ruby debugger to work. I discovered that there was a dependency problem
with the file:

C:\Ruby\lib\ruby\gems\1.8\gems\ruby-debug-base-0.10.3\lib\ruby_debug.so

A binary identical copy is also found in C:\Ruby\lib\ruby\gems\1.8\gems\ruby-debug-base-0.10.3\ext.

I used Microsoft's Manifest Tool to check if the manifests were actually part of the dll but they weren't. After adding
them manually and copying the updated ruby_debug.so over
to C:\Ruby\lib\ruby\gems\1.8\gems\ruby-debug-base-0.10.3\lib\ruby_debug.so everything worked ok.

I guess that step should be added to the Makefile.

Date: 2010-04-18 12:49
Sender: Rocky Bernstein

Peter Hug writes:
  I guess I'd look at how this is being done for other gems 
  which include build steps involving the C++ compiler.

If you do that and you have any suggestions pass that on.

Date: 2010-04-15 22:20
Sender: Pete Hug

Surely ruby_debug.so is not the only dynamic link library 
that is being built under windows with side by side assembly 
dependencies (e.g. MSVCR90.dll).

I do a lot of C++ work and I never use the manifest tool 
(mt). Instead, I use linker switches which achieve the same. 

I guess I'd look at how this is being done for other gems 
which include build steps involving the C++ compiler.

I hope this helps.

Date: 2010-04-15 18:15
Sender: Rocky Bernstein

I am no all that well versed with either Microsoft Windows nor
using ruby-debug from JRuby. In fact I was under the impression
that you didn't need ruby-debug-base at all, just ruby-debug
when using ruby-debug-ide.

Looking at http://forums.netbeans.org/viewtopic.php?p=69421 there
is a suggestion that some sort of "mt -manifest ..."
command should be run.

But as for changing the Makefile, well that's generated via "ruby
extconf.rb" I would imagine it should when to "mt"
to the Makefile or not.

So in sum, I'm not sure what to do here, and blindly adding something
for this situation may break some other situation.

Date: 2010-04-01 08:59
Sender: Pete Hug

More details can be found here: 
http://forums.netbeans.org/viewtopic.php?p=69421