In this study, we seek to contribute to theoretical understanding of the effect of trust on supply chain performance under different market environments. We are aiming to design the trust mechanisms suitable for network enabled organizations (Straub and Watson, 2002) to evaluate partners¡¦ trustworthiness on the fly of supplier choice. The sophistication of agent technologies in the future also can execute such supply chain negotiation based on the developed trust mechanisms. Before that, in this research, we use the multi-agent simulation system, Swarm, for simulating and analyzing the supply chain performance in four different market environments. Supply chain performance is evaluated using an example order fulfillment process of the mold industry to compare its performance with versus without trust mechanisms. Sensitivity analysis is used for examining the properties of the proposed trust mechanisms. We found that the trust mechanism will reduce the average cycle time rate and raise the in-time order fulfillment rate, but increase the unit cost of materials. Higher of trustor's propensity to trust results in higher in-time order fulfillment rate. This mechanism is better than just using quote price and due date, but it raises the unit cost of materials. The range of raised cost are controlled within 3%. We can consider this 3% additional material cost as the premium of the expectation of better quality and shorter cycle time.