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TLS (Transport Layer Security) is the most popular protocol used to secure communications over the internet today. This work explores how this protocol has evolved over the past 9 years and how effective the measures undertaken by the community have been to improve the adherence to best practices in the wild. TLS employs the use of certificates to initialize secure communication and make sure the other party is indeed who they say they are. We show that while security has improved over the years, a majority of certificates are invalid and outline reasons why. We also observe the growth of Certificate Transparency logs and show how the use of template certificates cause unexpected issues. 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