There have been interests to link different cuttings/cavings to various wellbore failure types during drilling. This concept is essential when caliper and image logs are not available. Identification of wellbore failure during drilling gives more chance of immediate actions before wireline logging program. In this paper, an approach was presented based on the image processing of ditch cuttings. This approach uses the sphericity and roundness of cuttings as input data to classify caving types and subsequently determine the dominant failure type. Likewise, common definitions of cavings were discussed initially before a new criterion is suggested. This quantitative criterion was examined by observations from caliper and acoustic image logs as well. The proposed approach and criterion were implemented on ditch cuttings taken from a well in Western Australia. Results indicate that the primary failure is shear failure (breakout) due to high levels of angular cavings. However, another failure due to the fluid invasion into pre-existing fractures was also recorded by blocky cavings.