A contents estimating system and method for providing an estimate of the cost of settling an insurance claim which includes a server having an embedded program compiled on the server and embedded in a web page, a client having a browser removably connected to the server, an inventory data acquirer for acquiring inventory data of each of the items that are the subject of the insurance claim and insert them into the web page, a price data acquirer for acquiring prices of the items of inventory data that are the subject of the insurance claim and insert them into the web page, and a liability limits data acquirer for acquiring liability limits data for the insurance claim and insert them into the web page, in which, upon receipt of a claim of loss from the insured, the web page is displayed on the screen of the client, the embedded program is executed within a client process with substantially unrestricted access to the client's system resources, and an estimate of the cost of settling a claim is produced by mapping an item of the inventory data to the price data, subject to the liability limits data, and is provided to the insured upon calculation, at the insured's location or the location of the loss.