Abstract Due to recent advances in the development of land data assimilation systems (LDAS) and the availability of high-quality, satellite-based surface soil moisture (SSM) retrieval products, we now have unambiguous evidence that the assimilation of SSM retrievals, or their proxy, can improve the precision (i.e., correlation versus truth) of surface state estimates provided by a land surface model (LSM). However, this clarity does not yet extend to the estimation of LSM surface water fluxes that are key to hydrologic and numerical weather forecasting applications. Here, we hypothesize that a key obstacle to extrapolating realized improvements in water state precision into comparable improvements in water flux accuracy (i.e., mean absolute error) is the presence of water state–water flux coupling strength biases existing in LSMs. To test this hypothesis, we conduct a series of synthetic fraternal twin data assimilation experiments where realistic levels of state–flux coupling strength bias—involving both evapotranspiration and runoff—are systematically introduced into an assimilation LSM. Results show that the accuracy of the resulting water flux analysis is sharply reduced by the presence of such bias, even in cases where the precision of soil moisture state estimates (e.g., SSM) is improved. The rescaling of SSM observations prior to their assimilation (i.e., the most common approach for addressing systematic differences between LSMs and assimilated observations) is not always a robust strategy for addressing these errors and can, in certain circumstances, degrade water flux accuracy. Overall, results underscore the critical need to assess, and correct for, LSM water state–water flux coupling strength biases during the operation of an LDAS. Significance Statement Land data assimilation is the process by which land surface model estimates of water states (e.g., soil moisture) and water fluxes (e.g., runoff and evapotranspiration) are improved via the incorporation of observations. Over the past decade, substantial improvements have been made in the precision of land surface model states via the assimilation of satellite-based soil moisture information. However, to date, these improvements have not yet been extended into water flux estimates like runoff and evapotranspiration. This is a critical shortcoming since advances in important weather and hydrologic forecasting applications are dependent on the improved estimation of such fluxes. We demonstrate that this shortcoming is linked to the inability of existing land surface models to accurately describe the impact of variations in water states on water fluxes and propose strategies for overcoming this issue in future land data assimilation systems.