Establishing an Environment for WinDBG on Mac OSX

Idea:

Trying to debug Windows XP using WinDBG on a Mac OSX computer. 

Purpose:

A how-to to set up WinDBG on Mac OSX using two virtual machines (Windows 7 & Windows XP)

Requirements:

• VirtualBox
• Windows 7 virtual machine (Debugger)
• Windows XP virtual machine (Debuggee)
• Mac OSX (host machine)

Steps:

1. Install WinDBG on debugger virtual machine (vm).
   Download link: http://www.microsoft.com/en-us/download/confirmation.aspx?id=8279

Follow the install instructions from the link on the download page
2. Go to VirtualBox Manager and click on settings for the debugger vm
   
   
   

   

   
   Click on Settings (yellow circle)

3. Navigate to the "Ports" tab and fill in the information from the below picture (you should not have to change the default IRQ and I/O Port)
   
   
   
4. Click "OK" and then click on settings for the debuggee vm
   
   
   
5.  Navigate to the "Ports" tab and fill in the information from the below picture (you should not have to change the default IRQ and I/O Port)
   
6. Click "OK" and start the debugger vm THEN the debuggee vm (if done the other way around, Virtualbox may pop up an error message about the path to the pipe file)
   
   
   
7. In the debuggee vm, click on Start-->Run then type "bootcfg /debug on /port com1 /baud 115200 /id 1" into the text box (without the surrounding quotes "") then press "OK"
8. 
9. Shutdown the debuggee vm
10. Go to the debugger vm and start WinDBG
    
11. Click File-->Kernel Debug then navigate to the "COM" menu and ensure that the information matches that of the below picture
12. 
13. Boot up the debuggee vm and WinDBG should display something like the following:
    
14. If so, it is working and you will have to wait for the debuggee OS to load. As this is happening, more information will show in the Command box of WinDBG. You are free to use WinDBG now. 

NOTE: If you want to use your debuggee vm without debugging it from the debugger vm, simply uncheck the "Enable Serial Port" box from the vm's settings under the "Ports" tab and press "OK"