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Colonial Christian missions have often been celebrated as catalysts of social reform in Kerala or dismissed as extensions of imperial empires. Various conversions among erstwhile ‘untouchable’ castes under the Church Missionary Society (CMS), London Missionary Society (LMS) and Basel Mission Society (BMS) have, thus, been criticized or celebrated, often at the expense of the converting untouchable’s agency. While the missionary accounts of conversion have been available in the form of various reports from the nineteenth century, ‘Dalit’ accounts of conversion and post-conversion dilemmas came forth into public, only in the second half of twentieth century through the literary works of Dalit and Dalit Christian writers. Novels like Samvatsarangal (1984) by S. E. James, Mukkany (1987) by D. Rajan, and short stories like “Eli, Eli, La’ma Sabach Tha’ni?” (2011) by Paul Chirakkarodu, “Achanda Vendinja Inna” (2003) by T. K. C. Vadutala and “Prethabhashanam” (2011) by C. Ayyappan reveal the dilemmas of Dalit Christianity, while songs by Poikayil Appachan, a.k.a Poikayil Yohannan or Poikayil Kumara Gurudevan, a Dalit convert who later rejected Christianity to start his own cult, Prathyaksha Raksha Daiva Sabha (Church of God of Visible Salvation), to fight casteism are important for understanding the multifarious nature of colonial Christian missions. This article highlights the entangled nature of religious experience embroiled in converting ‘untouchables’ in Kerala and how this entangled process influenced emergent Dalit Christian Theology in the postcolonial period. The paper will focus on the tactics and strategies involved within Dalit conversion experiences from Kerala, drawn from the theorisation of everyday life, and its caste-religion liminality to emphasize the literary expression of multicultural and multi-religious entanglements and its emotions in 19th and 20th century Kerala.