With society's increased dependence on information communication systems, the need for dependable, trustable, robust, and secure adaptive systems becomes ever more acute. Modern autonomic message-oriented middleware platforms have stringent requirements for self-healing, adapting, evolving, fault-tolerance, security, and active vulnerability assessment, especially when the internal working model of a system and the environmental influences on the system are uncertain during run-time. In this paper, we present an adaptive and evolving security approach, and adaptive trust management approach to autonomous messaging middleware systems. This approach learns, anticipates, evolves, and adapts to a changing environment at run-time in the face of changing threats. The approach combines adaptive risk-based security, trust-based security, and security-based trust: the resultant supra-additive synergy improves and increases the strength of security and the degree of trust in the system. The approach also integrates different metrics, assessment tools, and observation tools that improve and increase the assessability and verifiability of the trustworthiness of the system. Validation of results is through industrial case studies and end-user assessment.