Methods and apparatus for detecting or predicting surgical tool-bone skiving are disclosed. In some embodiments, the surgical tool is movably and/or snugly disposed within a guide-sleeve. In some embodiments, a magnitude of a lateral force between the surgical tool and the guide-sleeve is measured (e.g. by a force sensor or strain sensor). The present or future skiving may be detected or predicted according to the magnitude of the lateral force. In some embodiments, an alert signal is generated in response to the detecting or predicting of the skiving.