Providing effective tools to inoculate systems with a microbiome that can reliably improve plant functioning is an essential and immediate need in agriculture. From improved nutrient uptake and stress tolerance to growth promotion and pathogen resistance, plant-associated microorganisms provide their hosts with the fitness advantages necessary to maintain function and resilience in the face of change. Studies have identified many microbial taxa that can aid plants’ ability to thrive under stress; however, successful inoculation of key microbes in a field setting is inconsistent. Individual microbial taxa and microbial consortia often cannot successfully compete or thrive once they are introduced to a native microbial community that is already adapted to the dynamic field environment. This special session assembles experts across a diverse range of institutions to shed light on some of the challenges and potential resolutions to this very complex issue. We will highlight some of the progress made in understanding interactions among natural and introduced microbial communities, and emerging methods that may be used to improve applications of beneficial microorganisms in field settings. The session will include an introduction followed by short panelist presentations outlining current progress in addressing aspects of community functions, technology gaps, policy issues, and attempts to overcome the difficult nature of successfully implementing microbial inoculations in the field. We will then open the discussion to the audience and panel members to engage in a meaningful conversation of the many challenges impacting this emerging field.