This document summarizes early enterprise architecture challenges from the 2000s. It describes how organizations initially had monolithic systems with siloed departments and technology stacks, leading to inefficient processes like ETL and batch jobs. It then outlines how software practices began adopting best practices like design patterns and agile methods. The advent of the web introduced challenges around interoperability, security, and real-time capabilities. This drove innovations in technologies like XML, BizTalk, and SOAP to enable integration. System administration was complex with dependencies and different operating environments. There was a movement towards virtualization and containers as precursors to more modern approaches.