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Answer: Since only you and the UPS clerk were present when you shipped your package, this could have been one of those he-said-she-said situations that are never resolved. But the circumstances surrounding your dispute provided you with some extra leverage.

Another important detail you had going for you was your own shipping history. During their dispute investigations, companies like UPS sometimes look for outliers from a customer’s usual shipping history and preferences. Your record of shipping high-value shipments with excess insurance coverage helped convince UPS to agree on reimbursing you the full $375 value of your lost package.

Tip: A few simple precautions can assure a problem-free reimbursement in the future. Just because this particular UPS clerk forgot to ask you about the package’s value – let alone have you fill out the label on your own – obviously does not mean that you shouldn’t bring it up yourself. Furthermore, creating a UPS account can help you sidestep this problem next time. Account holders can fill out label forms online (the question about insurance will come up automatically) and print the label right from home.

Reporting by: Alex Horowitz

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Having a financial nightmare? E-mail Donna Rosato at money_helps@moneymail.com