In recent years, the use of Content Management Systems (CMS) as the core tool to define a Web application has gained popularity. However, the Model-Driven Web Engineering methods are not well fitted into the CMS domain. The main reason is that these methods are mainly focusing on the data and navigation aspects. To address this problem we propose in this chapter the use of Situational Method Engineering in order to detect the potential issues and improvements of a Web Engineering method in the CMS domain. Specifically, the suitability of the OOWS method in the context of CMS-based Web applications is evaluated by means of a user-registration use case. From the results of this evaluation, a list of current limitations of the OOWS Method in the CMS domain are detected. Additionally the improvements that can be applied from a SME perspective are introduced.