Forty years ago, “primitive land plant spores” meant simple triletes.  Happily, that was consistent with those spores produced by plants considered to be primitive based on other features.  All was right with the world.  Then, along came Jane Gray and Art Boucot, hoisting the banner for permanent tetrads (produced by few extant land plants) and dyads (produced by no extant land plants),and the era of the cryptospores was born.  Comfort was banished, conformity upended, a flame of confusion ignited.  In the ensuing forty years, we have learned a great deal about the types of plants that predated anything like is present in the extant flora.  And we have done so based on the excellent labors of a number of scientists working with scant (but sometimes extraordinary) material and a rich but sometimes cryptic spore record.  Simple trilete spores are now known to occur as early as the Late Ordovician, and geometrically regular cryptospores as early as the mid-Ordovician.  But we are in the midst of another spasm of discovery.  This one, too, is generating controversy about what kinds of organisms produced these spores (plants, algae, or something in between), and pulling us deeper and deeper into the Paleozoic and beyond.  These “cryptospores” are less geometric, and we do not yet have any sporangial fragments to demonstrate their production by embryophytes.  But, they occur with other types of tantalizing and enigmatic remains.  Their walls are more robust than any extant alga, and the walls of some appear nearly indistinguishable from some extant liverworts.  This talk will  summarize the information gathered to date on these early cryptospores, present new evidence on attempts to identify modern analogues (e.g., desiccation resistant algal cells), and suggest a revised time line of the events that we believe may have occurred in terrestrial autotrophs as they colonized the land surface beginning in the late pre-Cambrian.