So different, yet so alike, Canada and Australia, the land of wilderness and the land of bushes respectively, are two nations that go back thousands of years with their culture, practices, traditions, and the natives’ deep and sacred relationship with the land. The arrival of the Europeans disrupted the peace and the pattern of their lives, resulting in loss of indigenous lands, languages, cultures, and misplaced identity. Kenneth T. Williams, in his play In Care, draws attention to the flaws and loopholes in the system that trap natives like spider-webs. The second play taken up for study is Aliwa! by Dallas Winmar, an Australian play that recounts the journey of a mother, who strives hard to escape the clutches of the system trying to break her and her children up. While much research has been done on the sufferings and trauma of the native people, what really transpires on the other side is mostly kept in the dark. This paper examines how the colonial systems in Canada and Australia mirror each other in multiple aspects. It also draws attention to the systems established in colonial Canada and Australia, which aimed at obliterating any and all vestiges of Aboriginality, under the pretext of ‘civilizing’ the uncivilized. The paper utilises a play from each nation to validate the central objective of the paper, with a particular emphasis on the act of taking Aboriginal children away from their parents, a strategy used by the colonizers in both nations.