Abstract: Methods and apparatuses, including computer program products, are described for determining a customized and beneficial asset withdrawal from an investment portfolio account. A server computing device receives (i) customer portfolio data associated with a customer's investment portfolio account, (ii) research data associated with securities and share amounts, and (iii) customer preference data. An optimization engine executing in the server analyzes the customer portfolio data, research data, and customer preference data to generate an asset withdrawal optimization plan. The engine determines a proposed withdrawal of securities and share amounts out of the account, where the proposed withdrawal maximizes a benefit value to the customer and matches a predetermined asset withdrawal amount. The engine selects a set of securities and share amounts in the account that conforms to the proposed withdrawal and generates the optimization plan. The engine transmits the optimization plan to a remote device.