Controlled environment facility maintained digital wallets for residents of controlled environment facilities may be created and maintained in accordance with rules and regulations of the respective controlled-environment facility. Entry of data associated with an account outside the controlled-environment facility may be received from the respective resident and inserted in the digital wallet associated with the resident as a funding source. Resident controlled-environment facility trust, communications, commissary, media, or other account(s), associated with the resident, may be created in, or assigned to, the resident’s digital wallet. Th(is)(ese) account(s) may be funded using the outside account data in the resident’s digital wallet. Payments for provision of goods or services to the resident, within and in accordance with rules and regulations of the facility, may be made from the resident’s digital wallet by automatically debiting payments from (an) appropriate resident account(s) in the resident’s digital wallet.