The present study has identified, after due empirical testing, seven technology-related trust issues and three environment-related trust issues that help in building trust in B2B e-commerce. The technology-related trust issues include security, privacy, authentication, non-repudiation, web interface, system infrastructure and performance and technology related policies and procedures. The environment-related trust issues include socio-cultural environment, technical standards and regulatory environment. Any strategy to enhance levels of trust in B2B e-commerce should focus on these issues and attempt to deploy and implement suitable technologies in an efficient and effective manner. As most of these technologies entail significant fixed costs (mostly sunk costs), the size of the company is expected to be an important factor in determining the trade off between the costs and the benefits of deploying the given technology and related practices. In addition, other attributes of the company such as focus of B2B e-commerce and the nature of business may play an important role in such decisions. In the remaining part of this chapter, an attempt has been made to identify relevant technologies and the related benchmark practices regarding implementation of these technologies. The observed behavior of the companies belonging to different categories on the basis of size, focus of B2B e-commerce and nature of industry, has also been discussed.