The major power system blackouts that occurred in 1965, 1977, 1996, 1998, and 2003 notably involved incorrect relay operations. Most of these events occurred due to cascading failures which are partly deterministic and partly due to random aggravated circumstances. Traditional power system tools have the capability to analyze the first or the second event following a major disturbance. Dynamic Contingency Analysis Tool (DCAT) has been developed to overcome these shortcomings and analyze the cascading process for a number of what-if scenarios. Some of the unpredictable scenarios; intermittent generation as well as maloperation of protection system; have been analyzed in this paper. This paper also presents enhancements to DCAT that create chronological dispatch data to mimic the real world generation schedules due to load/generation intermittency and protection maloperation on cascading outages. This paper presents what-if scenarios for i) impact of chronological intermittent load and generation and ii) the consequences of unintended operation of protection relays on severity of outages caused due to severe contingencies.