An essential ingredient of the smart grid is software-based services. Increasingly, software is used to support control strategies and services that are critical to the grid's operation. Therefore, its correct operation is essential. For various reasons, software and its configuration needs to be updated. This update process represents a significant overhead for smart grid operators and failures can result in financial losses and grid instabilities. In this paper, we present a framework for determining the root causes of software rollout failures in the smart grid. It uses distributed sensors that indicate potential issues, such as anomalous grid states and cyber-attacks, and a causal inference engine based on a formalism called evidential networks. The aim of the framework is to support an adaptive approach to software rollouts, ensuring that a campaign completes in a timely and secure manner. The framework is evaluated for a software rollout use-case in a low voltage distribution grid. Experimental results indicate it can successfully discriminate between different root causes of failure, supporting an adaptive rollout strategy.