Cloud computing passed the hype cycle long ago and firmly established itself as a future technology since then. However, to utilize the cloud as cost-efficiently as possible, a continuous monitoring is key to prevent an over- or undercommissioning of resources. In large-scaled scenarios, several challenges for cloud monitoring, such as high network traffic volume, low accuracy of monitoring data, and high time-toinsight, require new approaches in IT Operations while considering administrative complexity. To handle these challenges, we present DEAR, the Distributed Evaluation of Alerting Rules. DEAR is a plugin for monitoring systems which automatically distributes alerting rules to the monitored resources to solve the trade-off between high accuracy and low network traffic volume without administrative overhead. We evaluate our approach against requirements of today’s IT monitoring and compare it to conventional agent-based monitoring approaches.