A machining condition estimating apparatus, and method, for estimating a machining condition to suppress a wear volume of a tool when conducting cutting work in a work machine are provided. For example, an analysis model presenting shapes of a tool and cutting material, may be defined, to be a target of analysis, and an initial value for use of analysis and change volume of the machining condition parameter as analysis parameters may be set up. Coordinates for tool and cutting material contact may be calculated. Moreover, a boundary movement rate, a maximum contact length, and a contact angle are calculated. A machining condition presented by the analysis parameter may also be searched and outputted.