Enterprise Architecture (EA) can support e-government initiatives within Dutch governmental organizations. It intends to manage the growing complexity on IT caused by these initiatives, by defining a set of organizational principles which are used to standardize business processes, systems and applications. EA can be seen as a product, but also as a process. It is a product which opts for communication among stakeholders, by its layered model. These layers (business, information, and technical) each define a specific view of the system and categorize different design goals for the organization to reach and to discuss. The process can be visualized as a path in which multiple stakeholders participate within decision-making processes to shape the EA. To extend on the product and process view on EA, an architectural change-trajectory (ACT) can be envisioned as the reform effort supported by projects within various departments of the organization, in which multiple stakeholders are participating and negotiating in developing Enterprise Architecture. Despite all long term investments and efforts on ACT’s, the overall effectiveness of them can vary within Dutch governmental organizations. In this research, we investigated this varying effectiveness by certain factors that have a great effect on it, mainly pronounced as implementation challenges. A literature study identified various implementation challenges which were reflecting the critical notes of authors on EA development. The resulting outcome was that most of these implementation challenges were mainly related to organizational complexity issues and dealt with the usage of EA Frameworks and Models. Therefore these aspects are investigated into more detail. In addition, three case study descriptions based on interview data were identifying new or similar implementation challenges opposed to the literature study. Each case study reflected a unique view on an ACT within a Dutch municipality. All output of this research lead to the structuring of an analytical framework, whereby feasible solution arrangements are embedded for a great part of implementation. The findings and recommendations should appeal to a broad audience including architects, business managers as well as consultants.