The performance of an exemplar-based scene classification system depends largely on the size and quality of its set of training exemplars, which can be limited in practice. In addition, in nontrivial data sets, variations in scene content as well as distracting regions may exist in many testing images to prohibit good matches with the exemplars. Various boosting schemes have been proposed in machine learning, focusing on the feature space. We introduce the novel concept of image-transform bootstrapping using transforms in the image space to address such issues. In particular, three major schemes are described for exploiting this concept to augment training, testing, and both. We have successfully applied it to three applications of increasing difficulty: sunset detection, outdoor scene classification, and automatic image orientation detection. It is shown that appropriate transforms and meta-classification methods can be selected to boost performance according to the domain of the problem and the features/classifier used.