identifying, by one or more processors, a point of interest for a trip to which a vehicle will navigate in an autonomous driving mode;

receiving, by the one or more processors, inputs from one or more systems of the vehicle;

in response to receiving the inputs, generating, by the one or more processors, one or more real-time messages including a set of contextualized details regarding at least one of a condition or a situation relevant to the trip;

determining, by the one or more processors based on the set of contextualized details, a level of uncertainty indicating a likelihood as to where at least one of a pickup location or a drop off location will be for the point of interest, wherein the level of uncertainty is based on one or more factors associated with the point of interest at a point in time as indicated by the set of contextualized details; and

causing, by the one or more processors, at least a portion of the set of contextualized details and visualization information to be displayed on a map on a user interface, the visualization information indicating a real-time graphical representation of the level of uncertainty using at least one of shading, highlighting, color, or a gradient.