Trip Delay CSR, filed June 22, honored June 30
Delayed outbound from SYR to JFK, missed connection requiring an overnight in NYC. Expenses were hotel (Sheraton JFK), dinner, and a $50 charge to confirm a seat on the new Virgin flight the next morning. (I hope when Alaska is fully integrated, this fee gets waived for status passengers)
Reason for delay: told weather at airport. Contacted JetBlue customer service by phone two days later to ask for military excuse, agent had never heard of it so put me on hold to get a manager. Received email from manager indicating "weather and flight crew".
Expensed $308 June 22, claim honored at $258 June 30 (no details but I inferred the $50 confirmation cost was not covered). Called Chase to ask if confirmation charges always fall outside of "reasonable expenses"; for the purposes of trip delay protection, it appears they do. I was a bit disappointed in this as I was well under the $500 limit, but understand their application of the rules.
All in all, relatively straightforward first experience with this benefit.