A computing device and method for use in enabling contextual ink annotation in a mapping interface are disclosed. In one aspect, the computing method may include receiving a map view request to render a map view of map data based upon a current map rendering context, determining that a previously created virtual ink annotation is associated with a location within the map view, the virtual ink annotation having a previous map rendering context captured at a time of creation of the virtual ink annotation, and comparing the current map rendering context to the previous map rendering context associated with the virtual ink annotation. The method may further include, based on a result of the comparison, controlling display of the virtual ink annotation in a rendered map view.