Modern deep learning has enabled amazing developments of computer vision in recent years (Hinton and Salakhutdinov, 2006; Krizhevsky et al., 2012). As a fundamental task, semantic segmentation aims to predict class labels for each pixel of images, which empowers machines perception of the visual world. In spite of recent successes of fully convolutional networks (Long etal., 2015), several challenges remain to be addressed. In this thesis, we focus on this topic, under different kinds of input formats and various types of scenes. Specifically, our study contains two aspects: (1) Data-driven neural modules for improved performance. (2) Leverage of datasets w.r.t.training systems with higher performances and better data privacy guarantees. In the first part of this thesis, we improve semantic segmentation by designing new modules which are compatible with existing architectures. First, we develop a spatio-temporal data-driven pooling, which brings additional information of data (i.e. superpixels) into neural networks, benefiting the training of neural networks as well as the inference on novel data. We investigate our approach in RGB-D videos for segmenting indoor scenes, where depth provides complementary cues to colors and our model performs particularly well. Second, we design learnable dilated convolutions, which are the extension of standard dilated convolutions, whose dilation factors (Yu and Koltun, 2016) need to be carefully determined by hand to obtain decent performance. We present a method to learn dilation factors together with filter weights of convolutions to avoid a complicated search of dilation factors. We explore extensive studies on challenging street scenes, across various baselines with different complexity as well as several datasets at varying image resolutions. In the second part, we investigate how to utilize expensive training data. First, we start from the generative modelling and study the network architectures and the learning pipeline for generating multiple examples. We aim to improve the diversity of generated examples but also to preserve the comparable quality of the examples. Second, we develop a generative model for synthesizing features of a network. With a mixture of real images and synthetic features, we are able to train a segmentation model with better generalization capability. Our approach is evaluated on different scene parsing tasks to demonstrate the effectiveness of the proposed method. Finally, we study membership inference on the semantic segmentation task. We propose the first membership inference attack system against black-box semantic segmentation models, that tries to infer if a data pair is used as training data or not. From our observations, information on training data is indeed leaking. To mitigate the leakage, we leverage our synthetic features to perform prediction obfuscations, reducing the posterior distribution gaps between a training and a testing set. Consequently, our study provides not only an approach for detecting illegal use of data, but also the foundations for a safer use of semantic segmentation models.