<p>I frequently need to debug .NET binaries on test machines (by test-machine, I mean that the machine doesn't have Visual Studio installed on it, it's frequently re-imaged, It's not the same machine that I do my development on, etc). </p>

<p>I love the Visual Studio debugger, but it's not practical for me to install visual studios on a freshly imaged test-machine just to debug an assertion or crash (the install takes way too long, the footprint is too large, etc).  </p>

<p>I'd really like a quickly installed program that could break into a running process, let me specify the location of symbols/source code, and let me jump right into debugging.  For native binaries, windbg works great, but I haven't found anything similiar for managed binaries. Any recommendations?</p>

<p>(as a side note, I am aware of visual studios remote debugging capabilities, but for some reason it never seems to work consistently for me...  I often have connection issues)</p>

There is always
mdbg
and
cordbg
, but I would suggest digging more into why remote debugging doesn't work consistently.
VS2005/8 seem a lot more reliable than earlier versions here (though I primarily do unmanaged) and it saves you from having to have the symbols accessible on the target machine.