A guided sampling tool guides the sampling of datapoints in large datasets. Generally, the guided sampling tool applies a machine learning algorithm to a database of historical issues encountered by an organization to guide the sampling of a large dataset. The guided sampling tool can evaluate and change provided variables and weights for performing a sampling. After the datapoints are sampled, the guided sampling tool compares the historic transactions represented by those datapoints to baseline images to determine if the historic transactions encountered a problem or issue, which would affect the overall quality assessment.