Research has consistently demonstrated the potential of print media to perpetuate negative and stigmatizing depictions of people with mental ill-health. There are particular concerns in small, remote, or isolated regions where reporting may have a disproportionate impact due to lack of anonymity. We aimed to assess how recent print media depictions of mental illness, published in the island nation of Bermuda, have changed compared to previous decades. All articles relating to mental illness published in Bermuda’s newspapers in 2021 were assessed for features relating to language, tone, and content. These were compared to articles from 1991, 2001, and 2011 using Pearson’s chi-squared test. 100 articles from 2021 demonstrated statistically significant improvements in reporting compared to all other years. This included a reduction in negative, stigmatizing and metaphorical language, increased mental health professional consultation and increased proportions of articles with positive overall tone and primary themes relating to Education, Information, and Recovery. Despite significant improvements in language, tone, and theme, several articles appeared to breach the Bermuda Media Council’s code of practice (e.g., using prejudicial or pejorative terminology).