A transactional messaging system displaying financial transactions in a user interface structured to resemble an email messaging user interface and/or an instant messaging user interface. The financial transactional messaging system presents and interacts with the financial transactions as email or instant messages, reducing the complexity of tracking, managing and processing transactions while preserving the full capabilities of a transaction processing system. Different transactions scenarios, such as requesting money, sending money, refunding a payment, sending payouts, cash on delivery (COD) and other financial transactions are presented utilizing different transactional process types that are organized under different mailbox folders such as inbox, sent items and deleted items. Inside each folder, the different transactions appears as emails that can be read, processed (pay, accept, release funds, decline, etc.) and/or with graphical elements like icons reflecting the current transaction attributes such as state or the actual activity performed by the transaction on the user's account. Relationships between a user selected transaction and the parties involved in the transaction in the role of payee or payor, are illustrated using email based schemes such as sender/recipient that focus on the selected transaction to avoid confusion due to information overload.