Ten cases of dryline-initiated convection are simulated from 2011 to 2013 within an OSSE framework. Ensemble simulations are produced from a cycling system that utilizes the Weather Research and Forecasting (WRF) model v3.3.1 within the Data Assimilation Research Testbed (DART). A one-way nested configuration with three domains at 36, 12, and 4-km grid spacing is setup using the EAKF data assimilation procedure. The ensemble is cycled for 48 hours prior to forecast initialization, with adaptive inflation and covariance localization utilized. A “truth” (nature) simulation is produced by supplying a 4 km WRF run with GFS analyses and integrating the model forward ~78 hours, from the beginning of ensemble initialization through the end of the forecast. Each nested domain extracts observations from the nature run, with random error from a normal distribution added, and assimilates the observations every six hours during cycling. Target locations for surface and radiosonde observations are computed six hours into the forecast based on a chosen scalar forecast metric (e.g., maximum reflectivity at convection initiation). A new forecast is initialized six hours after the prior forecast was initialized, assimilating observations based on the following three experiments: (1) Only the targeted observations are assimilated; (2) A swath of observations outside of target areas are assimilated (i.e., random observations); (3) Both targeted and random observations are assimilated. Using these methods, a proper analysis of the impact from targeted observations is accomplished for dryline convection forecasts.