Various embodiments of the present disclosure performing conversation sentiment monitoring for a conversation data object. In various embodiments, a text block that can be resized is identified within a conversation data object and successive regularized sentiment profile generation iterations are performed until a regularized sentiment score of the block exceeds a regularized sentiment score threshold. A current regularized sentiment profile generation iteration involves determining a regularized sentiment score for the block based on an initial sentiment score, a subjectivity probability value, and, optionally, a stage-wise penalty factor. A determination is then made as to whether the score exceeds the threshold. If so, then a regularized sentiment profile of the conversation data object is updated based on the regularized sentiment score. If not, then the text block is resized and a subsequent regularized sentiment profile generation iteration is performed based on the resized block.