Ok for me. I got this when creating using mingw-w64 (native or cross-compiler). I'm not sure what the problem is, but if I build it using gcc mingw-w64 i686-5.1.0-posix-sjlj-rt_v4-rev0, then it creates (finally) debugged assemblies. Otherwise
(gdb) break main ... (gdb) r ... Cannot insert breakpoint 1. Cannot access memory at address 0x42445c <process basically hangs>
message 19 times out of 20, although sometimes it really worked (very rarely).
gdb 7.8.1 and 7.9.1 seemed to be able to debug the exe created. So this is probably not the gdb version that matters.
My current theory / suspect is either the gcc version, or perhaps sljl vs. dwarf2 "aspect" for the compiler [?] (i686-492-posix-dwarf-rt_v3-rev1 does not work, and cross-compilation with some form of gcc 4.9.2 was also not). Did not try to use other versions of gcc.
update: new gcc (5.1.0), but cross-compiling. I still got this glitch. The reason in this case was the dependency library that my assembly (FFmpeg) used, linking it (in this case libgme), which exports several erroneous "common" characters (when I create a static executable). Because of this, the "general" one creates a brake ( https://trac.ffmpeg.org/ticket/282 ), and somehow it also spins gdb. For example, perhaps linking to the SDL can do this with you. My thought is probably the error ld [?]
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