Extrapair fertilizations are an important factor in reproduction of many bird species. It has been suggested that pursuit of extrapair fertilizations provides a selective pressure capable of affecting the "ecological" attributes of some bird species. It is known that in some cases the pursuit of extrapair copulations is motivated by fertility assurance. That is, there are populations in which (i) some males and females cannot produce viable offspring, and (ii) there is no pre-copulatory way to choose a compatible mate. In such situations individuals mate for "economic" reasons and attempt to secure reproduction by copulating with multiple partners. Here we formulate and analyze a simple game theoretical model addressing the interplay between environmental constraints and the pursuit of fertility assurance via extrapair copulations in determining breeding synchrony. Our results indicate that breeding synchrony in such cases is determined by the magnitude of the costs (due to environmental constraints) of breeding asynchronously versus the worth of the attendant increase in extrapair opportunities.