A system that facilitates debugging of a computing cluster and/or distributed applications environment. A debugger component receives a debugging expression, and a constraint component includes both a static constraint engine (SCE) and a dynamic constraint engine (DCE) processes the debugging expression to automatically perform a debugging process on at least two processes of a plurality of processes. When the user creates a tracepoint or constraint breakpoint the expression is sent directly to the SCE, which parses the constraint and tracepoint expressions, reduces the expression by evaluating parts of the expression based on static values (such as process ID or filename), and passes the remainder on to each of the applicable DCEs. The DCEs register a breakpoint at the applicable location in the process, and upon receiving a breakpoint event, evaluates the remainder of the constraint expression on the dynamic data, and sends log and/or break event data back to the user for viewing.