This chapter shows how ISO-Space evolved from MITRE’s SpatialML. Both present a specification language for the annotation of spatial information on geographical names and landmarks and also directional information involving orientations. Unlike SpatialML, ISO-Space extended its scope to motions and motion-triggered dynamic paths. ISO-Space also generalized distance measures to measures of other types and dimensions so that spatial annotation can be integrated with other semantic annotation schemes such as temporal annotation (e.g., ISO-TimeML). I also discuss how spatial relators, called signals, are enriched with fine-grained specifications, especially related to directional or orientational configurations involving frames of reference. SpatialML is a compact and very simple annotation scheme and is made easily mappable to other geospatial annotation schemes. In contrast, ISO-Space is more expressive and complex than SpatialML, meeting semantic needs of interpreting complex spatial language and computational needs of application envisioned in the coming years.