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To achieve this, you will have to use a lookup table to add the group (i.e. Country) to the City you have in your database. The links @LordNeilLord has provided will give you a data file that you can bring into your workflow and connect to your data on the Country field using either the Join or Find and Replace tools. After you have done this, you can use a Summarize tool to group the data by the new Country field you have added and then Sum the customers to provide the output you are looking for.