In a rapidly changing environment, management of natural resources is essential. Currently the world is undergoing a rapid loss of biodiversity through extinctions caused by human activities. Despite the alarming rate of species endangerment and subsequent loss, efforts to reduce species loss have been met with a number of complications. It is evident that any effective environmental management policy for biodiversity is more likely than not to encroach on private, public and commercial interests. This study investigates implementation successes and challenges specifically of Ontario’s Endangered Species Act (OESA) within the larger context of Southern Ontario’s land use planning policies (i.e., Greenbelt Act, Oak Ridges Moraine Plan, Niagara Escarpment Plan) and the Biodiversity Strategy. The study explores the roles and capacity of the government and non-government institutions involved in implementing the legislation and identifies gaps through expert interviews. While it was found that together such initiatives have succeeded in raising the public profile of endangered species, difficulty in proper implementation remains. Generally, this arises from a lack of coordination between and within the responsible authorities, lack of meaningful engagement with stakeholders and insufficient institutional capacity. Incongruousness in the process and substance among the mentioned biodiversity conservation and land use planning measures leads to use of regulations without the desired result. Finally, a critique I offered on the single-species approach to conservation taken in the legislation and suggest an alternative approach that is transparent, adaptively managed, and engages stakeholders is suggested.