Embedded systems are often subject to constraints that require determinism to ensure that task deadlines are met. Such systems are referred to as real-time systems. Schedulability analysis provides a firm basis to ensure that tasks meet their deadlines for which knowledge of worst-case execution time (WCET) bounds is a critical piece of information. Static timing analysis techniques are used to derive these WCET bounds. A limiting factor for designing realtime systems is the class of processors that can be used. Typically, modern, complex processor pipelines cannot be used in real-time systems design. Contemporary processors with their advanced architectural features, such as out-of-order execution, branch prediction, speculation, prefetching, etc., cannot be statically analyzed to obtain tight WCET bounds for tasks. This is caused by the non-determinism of these features, which surfaces in full only at runtime.In this paper, we introduce a new paradigm to perform timing analysis of tasks for real-time systems running on modern processor architectures. We propose minor enhancements to the processor architecture to enable this process. These features, on interaction with software modules, are able to obtain tight, accurate timing analysis results for modern processors. We also briefly present analysis techniques that, combined with our timing analysis methods, reduce the complexity of worst-case estimations for loops. To the best of our knowledge, this method of constant interactions between hardware and software to calculate WCET bounds for out-of-order processors is the first of its kind.