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If you personally take the OfferUp packages to the Post Office, you should be able to buy separate insurance at the counter, but it will have a separate tracking number and will be EXPENSIVE. It is called "retail counter insurance" (available for "First-Class" mail).
I always take my USPS packages to the Post Office (rather than requesting package pickup) for all postal deliveries since this process guarantees that every single one of my packages get scanned and uploaded to the USPS servers.
You are covered up to $50 in terms of value of the damaged item. If you have filed a claim with USPS in the past, it's the same process (refer to USPS website with tracking info all the details).
On a sidenote, I would have thought that someone would inquire about these details before using the shipping option? I am perplexed at the number of OU users that start shipping without inquiring about the most important aspects of the logistical process.
@factsdontcareI'm perplexed that you as well are confused as I wrote earlier - USPS only covers you for $50 if you in fact shipped PRIORITY MAIL NOT Any other method like first class or such. As I'm new to shipping but have shipped many items recently and this would be the first broken item. Maybe have a little concern or understanding to those that are having some issues and their item is broken! Thanks for your feedback..
To clarify, OU's prepaid 1st class shipping label includes $50 valuation insurance.