Judging from the screenshots of Sleepy you provided, you probably didn't link against debug libraries. The callstacks are more or less useless in helping you find the problem because either a) something got really screwed up and the stack got corrupted or b) starting a new thread doesn't reveal anything above the initiation point. The main thread that runs your application and probably also crashes it is missing and that is the important one.
If you say you have dedicated testers, they should be given proper debug versions of the application and it should be run in a proper debug environment corresponding to your build toolchain. Hooking into an application after or during execution is very unreliable, even more so in Windows than on Linux and more often than not you won't end up with much useful information.
Sleepy also wasn't meant to be used as a generic debugging tool. It is a callgraph profiler as can be seen in the screenshots. As such I wouldn't be surprised if it isn't able to fully recover callstacks after an application has crashed.
It seems to happen when a lot of high-memory packets are sent at once.
Unless you can consistently isolate and reproduce this, it is probably just coincidence or just correlated in some indirect way.