Organizations in legal practice, under pressure to do “more for less,” are searching for ways to automate legal work, to improve efficiency of legal service delivery. Automated drafting of contracts (or: contract automation) is one of the areas where technology is—partly—replacing legal professionals. In Dutch legal practice, the number of organizations that are actively deploying contract automation is still relatively small, but growing. This chapter looks at experiences with contract automation of organizations from various sectors in Dutch legal practice. Contract automation can improve legal service delivery to consumers and SMEs, as well as contracting processes within organizations. Several organizations report positive results. However, successfully implementing contract automation, especially for internal use within organizations, is not simple. Tight budgets, resistance to change and poor integration with other software are some of the problems that organizations may encounter. Generally, human and organizational factors are often at least as important as the technological aspects. Successful implementation of contract automation requires design thinking, a proactive approach and process-oriented (legal) professionals. Regardless of these difficulties, the use of contract automation software in Dutch legal practice can be expected to increase, due to several factors. The number of organizations that are offering contracts (and other legal documents) online to SMEs and consumers has grown rapidly over the last years. Contract automation is not only offered to consumers and SMEs by commercial parties, but also by branch organizations, as a service to their members. Consumers and SMEs will become used to these self-help solutions for legal matters. Legal publishers are also increasing the offering of automated contracts and other legal documents. In addition, law firms and consultants are promoting the use of contract automation within client organizations. Finally, many corporate organizations are increasingly exchanging experiences on improving legal operations and the use of Legal Tech, including contract automation. Eventually, increased use of contract automation may drive further harmonization of contracts within sectors and facilitate other technological applications, such as the automated analysis of contracts.