This is simple to answer. If you don’t feel I’ve satisfied your inquiry, please elaborate more on the problem and I can also clarify further.
You do not ask for insurance on a US Money Order. If you make it payable to someone (not mailed out as blank), then only that person can redeem it. Whether they present it at a bank or at a post office, they will show ID to prove it was made payable to them and not someone else.
It doesn’t matter who delivered the money order on your behalf. If it is lost, stolen, or destroyed, the USPS will refund you. Just have that money order’s receipt stub available for presentation to prove it was you that paid for that money order.
You said you already understand there is a 60 day waiting period from the date the money order was printed before a refund will be considered by USPS. They will have you fill out a form, giving them the address where they will mail you your refund. If they deny the refund, saying their system shows it has been redeemed, then you know the recipient did get the money because you made it payable only to them so a thief could not cash it.