As non-vascular, early land plants with an aquatic ancestry, mosses do not regulate internal water conditions separate from that of their environment and as a result, evolved mechanisms to survive in a terrestrial world out of water. Yet, there is a widely accepted dogma that moss reproductive success is solely dependent on rainfall events carrying swimming, bi-flagellate sperm across the landscape to reproductively mature and receptive female mosses--but this classic view of moss reproduction may be too simplistic. In this dissertation I test the assumptions of reproductive limitation in mosses and present novel findings in a basal, yet understudied terrestrial plant mating system. I find evidence of environmental desiccation tolerance in moss sperm, thus offering the potential for stress-tolerant gametes on the landscape possibly suited for various transport vectors, reminiscent of a pollen grain. To investigate the broad evolutionary implications of this newfound complexity in moss sexual reproduction, I tested classic tenets of plant-pollinator theory on the ancient mosses and their ubiquitous microarthropod inhabitants. Experimental results show that mosses and microarthropods are engaged in a "pollination-like" syndrome guided by sex-specific volatile cues that differentially affect microarthropod behavior. These data indicate an existing complex mutualistic relationship and provides new evidence of sexually dimorphic investment by male and female mosses into reproductive success. Further, these data put forth the idea that female mosses challenge an inherent mate limitation by investing into reproductive assurance via maintaining a relationship with microarthropods. Experimental work further confirms a role for invertebrates in moss reproductive success and tests mutualism theory through ongoing experiments. Such experiments include an assessment of moss genetic diversity, paternity, and male fitness traits as it relates to mosses with or without the presence of microarthropods, thereby testing for fitness benefits gained by mosses possibly engaged in a transport mutualism with microarthropods. I further tested mutualism, community ecology and moss sexual reproduction concepts in extreme geothermal moss populations living at the edges of inhabitable Earth, and results show that even geothermal moss canopies are diverse and host differential and abundant life. In a first field test of mutualism I found that although extreme heat stress may constrain sexual reproduction in mosses, a correlation between within-population moss genetic diversity and microarthropod abundances exists. To further examine mosses in extreme environments, and how these environments may constrain sexual reproductive success, I evaluated the effects of simulated warming on Antarctic moss physiology and reproductive biology. Data indicates that simulated warming relieves mosses of physiological stress, and results in a greater investment into primary productivity and sexual reproduction. These data support the hypothesis that with less stress, sexual reproduction is increased. Mosses are an ideal system by which to understand organisms that exist in environments ranging from the mesic to the extreme, in the laboratory and the field and even in the classroom, where the small functioning ecosystem of mosses can be used for discovery-based biology education as described in the Mosscosms curriculum. This work contributes significantly to the field of bryophyte and plant biology by revealing novel insights into the biotic and abiotic drivers of sexual reproduction in mosses.