This article addresses the challenges of conveying connotative meaning in translation between English and Uzbek literary discourse. It proceeds from the finding that, although the two traditions share common pragmatic mechanisms of conveying connotation namely speech acts, presupposition, implicature and referential cohesion the means by which these mechanisms are realised differ in cultural and stylistic terms. In English literary discourse connotation is expressed more through lexical-stylistic register and the flouting of Gricean maxims, whereas in Uzbek literary discourse it is often reinforced through morphological devices such as diminutive suffixes, through folkloric-poetic formulas, and through cultural-religious notions. The article argues that the adequate transfer of connotation requires the reconstruction of cultural presuppositions, associative networks and emotional resonance rather than literal semantic correspondence, since failure to preserve the connotative dimension of culturally marked units may result in axiological distortion, false associations or a shift of meaning. It outlines a set of strategies functional equivalence, cultural compensation, contextual adaptation, explicitation of implicit codes and preservation of stylistic tone and presents translation as intercultural mediation that balances semantic accuracy with cultural intelligibility.