We describe recent work on designing an environment called Java PathExplorer for monitoring the execution of Java programs. This environment facilitates the testing of execution traces against high level specifications, including temporal logic formulae. In addition, it contains algorithms for detecting classical error patterns in concurrent programs, such as deadlocks and data races. An initial prototype of the tool has been applied to the executive module of the planetary Rover K9, developed at NASA Ames. In this paper we describe the background and motivation for the development of this tool, including comments on how it relates to formal methods tools as well as to traditional testing, and we then present the tool itself.