Systems for intelligent sorting of time series data for improved contextual messaging are included herein. An intelligent sorting server may receive time series data comprising a plurality of chat messages. The intelligent sorting server may determine a first order of the plurality of chat messages based on a chronologic order. The intelligent sorting server may use one or more machine learning classifiers to identify candidates for reordering the chat messages. The intelligent sorting server may generate a second order of the chat messages based on the identified candidates for reordering. Accordingly, the intelligent sorting server may present, to a client device, a transcript of the chat messages associated with the second order and an indication that at least one chat message has been repositioned.