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Decentralisation is changing the structure of electricity industries worldwide. Driven by Distributed Energy Resource (DER) deployment, this energy user-led transition poses new risks and opportunities. Despite its growing role, there remains limited understanding of DER behaviour in the field. An improved evidence base is required for DER integration that helps to achieve the energy trilemma of secure affordable and sustainable electricity. The aim of this thesis is therefore to better understand risks and opportunities for appropriate integration of DER in an increasingly decentralised electricity industry. Novel data driven and modelling techniques are developed for analysis of DER behaviour in the field. Australia is used as a case study given its high penetration of distributed photovoltaic systems (D-PV). Novel insights are gained through analysing high-resolution (30s to 5min) operational data from over 5,000 individual D-PV. Technical analysis of DER in the distribution network considers curtailment due to over-voltage tripping and finds that D-PV curtailment disproportionately impacts some energy users and may limit DER participation in the electricity industry. Security analysis focuses on DER behaviour during major power system disturbances that originate in the transmission network. Findings indicate that DER pose a growing risk to power system security yet can also act to support system security. Commercial analysis indicates both positive and negative impacts of DER behaviour for industry participants. Overall, DER behaviour is shown to be highly diverse, reflecting distribution network complexity, and highlighting the value of data driven analysis. Semi structured international interviews and engagement in policy making are undertaken to develop a framework. This framework ‘maps’ electricity industry decentralisation across technical, security, commercial, governance and social dimensions so that individual DER integration efforts can be understood within the broader transition landscape and key future work identified. It is concluded that data driven analysis offers valuable insights and that operational change is required to manage DER risk to power system security. Inverter performance standards are found to set a boundary around the role that DER can play, and appropriate DER integration may require strategic coherence across the electricity industry. Finally, social licence will likely impact the success of DER integration efforts.