A method, system, and program for facilitating presentation and monitoring of electronic mail messages with reply by constraints are provided. Within a network environment, a server receives electronic mail messages with separate selected reply by dates, wherein each electronic mail message is addressed for delivery by the server to at least one particular recipient. The server enables, for display within a user interface accessible to the particular recipient, a separate record for each electronic mail message within an inbox. The inbox include at least one selectable sublevel, wherein upon selection of the particular selectable sublevel of the inbox, only a selection of records for electronic mail messages with a same reply by date as the selectable sublevel are displayed within the user interface.