This paper proposes an efficient method to analyze the worst case interruption delay (WCID) of a workload running on modern microprocessors using a cycle accurate simulator (CAS). Our method is highly accurate because it simulates all possible cases inserting an interruption just before the retirement of every instruction executed in a workload. It is also (reasonably) efficient because it takes O(N log N) time for a workload with N executed instructions, instead of O(N²) of a straightforward iterative simulation of interrupted executions. The key idea for the efficiency is that a pair of executions with different interruption points has a set of durations in which they behave exactly coherent and thus one of simulations for the durations may be omitted. We implemented this method modifying the SimpleScalar tool set to prove it finds out WCID of workloads with five million executed instructions in reasonable time, less than 30 minutes, which would be 200-300 days by the straightforward method. Furthermore, our CAS-based analyzer may have a post process to calculate the WCID for multiple F interrupts with O(FN√N log N) time complexity.