A system and method supporting medical diagnosis made based on evaluation of images of a histopathology sample. The method includes automated generation and evaluation of a digitally-stained image (emulating the effect produced on the sample by a chosen specific dye) based at least on one of data representing an image of the HE-stained sample and empirical testing data representing samples stained with specific dyes. The system is adapted to acquire a multispectral image of the sample, to implement the digital staining of the sample's image, and to evaluate automatically the digitally-stained image contemporaneously with multispectral image acquisition. The system generates an output indicative of need to request a preparation of an actual specimen stained with chosen specific dye for further evaluation, reducing the number of samples prepared in anticipation of such request and reducing time lapsed prior to the evaluation by a histopathologist.