A computer, for planning moves of freight automatically adds one or more layover(s) to a mission. Next, the computer determines one or more charge(s) for the layovers, using carriers' rules. Thereafter, the computer uses the charge(s) in deciding whether to include the mission in a transportation plan to be executed. In some embodiments, the computer automatically maintains, for the given mission, counts of attributes on which limits are imposed by a government or by carriers, such as driving time, on-duty time, and driving distance, and when any count exceeds a corresponding limit in the midst of a driving activity, the computer automatically divides up the current driving activity into a truncated driving activity and a remainder driving activity, separated by a layover activity. The computer also determines an estimated time of arrival, including the impact of required layovers, to reach destination(s), and whether layover(s) is/are required at the destination(s), e.g. due to consignee's receiving hours or due to congestion at consignee's dock.