Either person can file the claim.
If postage & insurance were purchased on-line (such as Paypal postage): either party can file using an on-line form. http://www.usps.com/insuranceclaims/online.htm
In all cases, you can choose instead to file a form at the local post office (either party). Here is a link to the form and instructions: http://www.usps.com/forms/_pdf/ps1000.pdf
If anything was received (but damaged), it has to be submitted with the claim.
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