Father Winter really gives your roof a pounding every year. It's possible that the roof has sprung some leaks that might have been preventable. So, what causes roofing leaks during the winter, and what can you do to fix the issue? Here, you will learn just that. What causes winter roofing leaks? There are four issues that cause problems with roofing. These issues could individually cause problems or the problems could be caused by a combination of any of the four.