John; I mail out hundreds of insured packages.

My question is why is the postal clerk even asking what is inside your package? And secondly, are you volunteering that information? I've never been asked that question.

Insurance costs only $1.30 for up to $50 coverage via first class mail. $100 in coverage costs $2.20. Return receipts, certified mail does not pay anything in case of a loss. The only way to collect on a loss is by having insurance. I've had occassion to file a few claims due to losses and never has the claim been denied because they were casino chips. If contents are lost or missing, you must prove their value by using a standard catalog reference and value or copy of a receipt of what you paid for the item.