Abstract: Enterprise applications are complex systems that are hard to develop and deploy in organizations. Although software application development tools, frameworks, methodologies and patterns are rapidly developing; many projects fail by causing big costs. There are challenging issues that programmers and designers face with while working on enterprise applications. In this paper, we present the three of the significant issues: Architectural, technological and performance. The important subjects in each issue are pointed out and recommendations are given. In architectural issues the lifecycle, meta-architecture, guidelines are pointed out. .NET and Java EE platforms are presented in technological issues. The importance of performance, measuring performance and profilers are explained in performance issues.