Today’s general-purpose deep convolutional neural networks (CNN) for image classification and object detection are trained offline on large static datasets. Some applications, however, will require training in real-time on live video streams with a human-in-the-loop. We refer to this class of problem as Time-ordered Online Training (ToOT)—these problems will require a consideration of not only the quantity of incoming training data, but the human effort required to tag and use it. In this paper, we define training benefit as a metric to measure the effectiveness of a sequence in using each user interaction. We demonstrate and evaluate a system tailored to performing ToOT in the field, capable of training an image classifier on a live video stream through minimal input from a human operator. We show that by exploiting the time-ordered nature of the video stream through optical flow-based object tracking, we can increase the effectiveness of human actions by about 8 times.