This research builds on a previous investigation which found that the Minnesota Multiphasic Personality Inventory - 2 (MMPI-2), the most widely used personality assessment instrument in the world, exhibits significant cultural bias when used with American Indian adults. In trying to understand why this occurs, the confluence of American Indian worldview and colonizing attitudes inherent within test development were explored through an item-level analysis. A qualitative investigation of item content and relations to cultural and language factors in item interpretation followed. The language and cultural shifting necessary to answer the items contained within the MMPI-2 are significant enough to considerably negate the test's validity when used with American Indians. Through a series of in-depth interviews with thirteen Elders and leaders of an Eastern Woodland tribe, this study demonstrates how the MMPI-2 pathologizes Indigenous worldviews, knowledge, beliefs, and behaviors rather than accurately assesses psychopathology within this distinct cultural group. The results of this investigation also demonstrate that new culturally and contextually informed assessment tools are urgently needed. Attempting to answer the calls of fellow Indigenous scholars, this research aims to challenge and transform the status quo of assessment research in particular and psychological research in general by centering Indigenous perspectives. Further, it is an attempt to bring respect to the perspectives of Indigenous peoples and their right to psychological self-determination within the arena of psychological research, theory, and practice.