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Found the problem. The kernel was not defined right, and caused random behavior. I sure didn't need the debugger to tell me such useless information, or in any way indicate to me that there was a problem.

The bad way:

cv::dilate(image, image, cv::Mat(cv::Size(50,50),CV_8UC1));

The good way:

cv::dilate(image, image, cv::Mat::ones(50,50,CV_8UC1));