I am not sure whether this issue is related to MinGW or to GDB.
Since I don't have this issue on Linux / Mac and it only happens on Windows 7 + MinGW, I decided to post it here - maybe someone else on this list face this issue
in the past and can shed some light / provide some good tips on the matter.

Now to the actual problem:
When I debug my application which consists of many shared libraries ("dll"s, around 35 - 40) and I have a breakpoint set in one of the shared libraries 
the startup time of gdb is *very* slow ( I am talking here about 10 mins ).

If I remove all the breakpoints and start the debugger, the debug session starts in a reasonable manner (still very slow compare to Linux) ~45 seconds.
I can then place the breakpoints back and continue debugging. 

However, the above workaround does not work if I need to debug one of the shared libraries initialization code

Some info about my environment:

MinGW 4.6.1 (TDM) 32 bit - I tried the official one 4.7 from MinGW with no luck - the problem persists
GDB 7.05 (note that I tried all versions of gdbs available on MinGW SF download page, from 6.8.5 -> 7.4 with no luck)
Windows 7 64bit

For comparison: GDB 7.4 on my Ubuntu 12.04 starts the debugging session under 5 seconds for the same application

Any advise?

Eran Ifrah
Author of the cross platform, open source C++ IDE: http://www.codelite.org