The use of idioms in conversation among the Luhya speaking communities, especially during Witimbule Programme that is aired in Radio Mambo broadcast in Western Kenya, is common. Hardly does a social ceremony end without application of idioms among the Luhya people. The fact that they are interesting to use during the speeches, there are challenges that arise and if not resolved, they can cause misinterpretation, hence miscommunication. This study employs relevance theory by Wilson and Sperber (1995 /2002) which highlights that when the information is complex, it stands the risk of being misinterpreted or rejected by the mind. The study found that the hindrances to interpretation of idioms include deficiency in cognitive environment knowledge, dialectical constraints due to lexical mismatch among the Luhya speaking dialects ,lack of context ,ambiguity of idioms, lack of subject part of the idiom and lack of native speakers intuition .The results reveal that deficiency in cognitive environment knowledge was the main cause of difficulties encountered during interpretation of idioms in conversation among the Luhya speaking dialects. Dialectical variation contributed insignificantly to misinterpretation of idioms. From this assumption, the best strategy of interpreting idioms is the knowledge of cognitive environment approach besides others.