Is it possible to debug the target multiple times with the same binary application, without flashing the device?

Yes, you can debug the target multiple times with the same application.

1. Flash the target once with either using a target task (standalone) or using Flash Programmer > Flash File to Target .
   Note: For information about flashing using target task and flash file to target, refer I need to flash a large size application (more than 64 KB) , and I also need to perform target tasks, such as secure/unsecure the device and additional verify or erase. How do I do it? and Is there a way to quickly flash multiple boards with different S-Records?.
2. Select Run > Debug Configurations .

   The Debug Configurations dialog box appears.

3. Select Debugger > Download .

   The Download page appears in the Debug Configuration dialog box.

4. Clear the Perform Standard Download and Execute Tasks checkboxes.
   Figure 1. Download Page - Debug Configurations Dialog Box
   
   
   
   

   Now as the debugger does not need to flash a potentially large application, you can start debugging within a few seconds, and you can do this multiple times.

5. To flash the target, click the Flash Programmer button followed by the Debug button on the CodeWarrior IDE toolbar.
   Figure 2. Flash Programmer Button
   
   
   
   
   Figure 3. Debug Button
   
   
   
   

Now, you can debug the target multiple times with the same binary application, without flashing the device