After reading this question about seemingly degenerate behavior for the Windows memory allocator, and remembering back to this paper about constructing worst-case inputs to quicksort implementations, I started wondering: would it be possible to build a program that, given a black-box memory allocator, forces that allocator to fail an allocation request even when sufficient memory is still available in the system? That is, is it possible to take a black-box memory allocator and force it to fail?
I know that this can probably be done by allocating and freeing memory in a checkerboard pattern to force massive fragmentation, so in my mind an ideal solution would cause a failure to occur with the fewest total bytes allocated at the time of failure. With respect to the original post that inspired this, it could in theory be possible to cause a failure with zero bytes allocated if the memory allocator has an internal bug.
Any ideas/thoughts on how to do this?