GDB Incorrectly Reads & Resolves Shared Library Symbols [MinGW-w64]

Can anyone recommend a way to start debugging GDB? I've found that when I
compile a 32-bit shared library that GDB is unable to correctly resolve the
symbols in the image and set breakpoints. Even when I reach a segfault and
print the backtrace, the symbols are incorrect or flat out missing. I
already verified that the image has .debug_* sections as would be required
for DWARF debugging, so I'm perplexed as to why GDB cannot correctly
resolve it and am looking for guidance.

Thank you.