> Are there any interesting bugs and edge cases that you could share?
Too many to count, particularly the PDB format has so many absurdities in practice that I'm quite impressed they are so well supported even outside of Microsoft's ecosystem. For me one of the most fun aspects is that Microsoft's kernel tools instead of fixing up PDBs when performing certain optimizations on the object files, chose to instead attach additional maps in the PDB (OMAP) to remap everything. That decision makes handling of PDBs much more tricky than they otherwise would have to be.
In terms of actual bugs, there are too many to count. One of the more fun one in recent history is that Apple's tools are running up against limitations of some remaining 32bit offsets even in 64bit macho formats and now at times just overflows and you're stuck.
Are there any interesting bugs and edge cases that you could share? Always good to hear good war stories from production :)