Abstract: Aspects of the disclosure relate to an automated iterative predictive modeling computing platform that iteratively requests additional data from external data sources to iteratively generate a more accurate insurance premium estimation. In some instances, the automated iterative predictive modeling computing platform may generate an insurance premium estimation using affordable insurance data and using estimated data in place of missing data. If the insurance premium estimation does not meet predefined confidence thresholds, the automated iterative predictive modeling computing platform may retrieve additional data that is more expensive but also has a likelihood to generate a more accurate insurance premium estimation. This process may be repeated using different data sets from different external data sources until a sufficiently accurate insurance premium estimate is generated by the automated iterative predictive modeling computing platform.