A computer-implemented method comprising: receiving, by one or more processors of a server computing system, from a plurality of users (302, 304, 306, 308) in a joint positional tracking session traveling towards a common destination, positional data associated with a first user and a plurality of other users, the plurality of users comprising the first user and the plurality of other users; determining, by the one or more processors and based on the received positional data associated with the first user and the plurality of other users, that a separation parameter associated with the first user has exceeded a threshold separation value, the separation parameter associated with the first user representing a separation between the first user and another user of the plurality of other users; automatically generating, by the one or more processors in response to determining that the separation parameter has exceeded the threshold separation value, route updates for reducing the separation parameter between the first user and the other user in the joint positional tracking session to below the threshold separation value; and transmitting, by the one or more processors, the route updates to the first user and the other user in the joint positional tracking session, wherein the route updates transmitted to the first user and the other user comprise a regrouping waypoint for the first user and the other user to reconvene; wherein the separation parameter associated with the first user represents a distance between the received positional data associated with the first user and received positional data associated with the other user, the other user being a closest other user to the first user. receiving, by one or more processors of a server computing system, from a plurality of users (302, 304, 306, 308) in a joint positional tracking session traveling towards a common destination, positional data associated with a first user and a plurality of other users, the plurality of users comprising the first user and the plurality of other users; determining, by the one or more processors and based on the received positional data associated with the first user and the plurality of other users, that a separation parameter associated with the first user has exceeded a threshold separation value, the separation parameter associated with the first user representing a separation between the first user and another user of the plurality of other users; automatically generating, by the one or more processors in response to determining that the separation parameter has exceeded the threshold separation value, route updates for reducing the separation parameter between the first user and the other user in the joint positional tracking session to below the threshold separation value; and transmitting, by the one or more processors, the route updates to the first user and the other user in the joint positional tracking session, wherein the route updates transmitted to the first user and the other user comprise a regrouping waypoint for the first user and the other user to reconvene; wherein the separation parameter associated with the first user represents a distance between the received positional data associated with the first user and received positional data associated with the other user, the other user being a closest other user to the first user.