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STM32F102 - ST-Link/V2, Difficulty Entering debug mode

I am working on a product that utilizes an STM32f102R6 processor and am having difficulty setting the device up with uVision 5.25.2.0 for debug. I am using an ST-Link/V2 for this purpose (firmware V2.J29.S7). I am able to compile and flash the code to the device ad have verified this by validating the flash data with the ST-Link utility. When I enter debug mode, I am able to step through the disassembly window, but am unable to step through the C-code.
I was previously able to debug using an PE-multilink universal, but it would occasionally crash, so I moved to the ST-Link/V2 with the hope that I could resolve the crashing issues.
Here is my configuration:

Boot0 is pulled high and Boot1 is pulled low.

If I do not do this, the SW Device indicates an “internal command error”. This seems odd to me as I must then run out of the system memory. The address space in the disassembly window is indicative that the program never leaves the system memory.

Optimization is set to level 0

The system uses an 8MHz external crystal and a 48MHz system clock.