A system and method for assisting a user to enter data are provided. The method includes detecting a user's selection of a moveable input zone on each of one or more input documents displayed on the user's screen and detecting a user's selection of a moveable target zone on a target document displayed on the user's screen. Data in the input zone(s) and the target zone is captured for one or more locations of the respective zones and a pattern is learned automatically for filling additional data in the target document based on the captured data. A fill arrangement for filling the additional data in the target document based on the learned pattern is generated, which can be presented to the user for validation.