This paper takes a close look at the landscape of the Automatic Identification System (AIS) as a major source of information for maritime situational awareness (MSA) and identifies its vulnerabilities and challenges for safe navigation and shipping. As an important subset of cyber threats affecting many maritime systems, the AIS is subject to problems of tampering and reliability; indeed, the messages received may be inadvertently false, jammed, or intentionally spoofed. A systematic literature review was conducted for this article, complemented by a case study of a specific spoofing event near Elba in December 2019, which confirmed that the typical maritime AIS could be easily spoofed and generate erroneous position information. This intentional spoofing has affected navigation in international waters and passage through territorial waters. The maritime industry is neither immune to cyberattacks nor fully prepared for the risks associated with the use of modern digital systems. Maintaining seaworthiness in the face of the impact of digital technologies requires a robust cybersecurity framework.