Privacy concerns in internet communications are increasing steadily among citizens who reside in both repressive regimes and other developed countries, due to the technical network interception possibilities which threat personal rights and freedom. Moreover, identifying personal identity and other private data of internet users can be easily categorized as an emerging risk which may hinder freedom of speech and other democratic rights. Due to privacy concerns and other factors mentioned above, usage of anonymity technologies on the Internet is growing. In this research, we take a closer look at the anonymization technologies, from a risk analysis perspective in terms of success rate to circumvent internet censorship efforts. Furthermore, we investigate what is the current status of Internet censorship in wide variety of nations, taking into account the couple of recent reports published by reputable sources.