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Today's system monitoring tools are capable of detecting system failures such as host failures, OS errors, and network partitions in near-real time. Unfortunately, the same cannot yet be said of the end-to-end distributed software stack. Any given action, for example, reliably transferring a directory of files, can involve a wide range of complex and interrelated actions across multiple pieces of software: checking user certificates and permissions, getting details for all files, performing third-party transfers, understanding re-try policy decisions, etc. We present an infrastructure for troubleshooting complex middleware, a general purpose technique for configurable log summarization, and an anomaly detection technique that works in near-real time on running Grid middleware. We present results gathered using this infrastructure from instrumented Grid middleware and applications running on the Emulab testbed. From these results, we analyze the effectiveness of several algorithms at accurately detecting a variety of performance anomalies.