Let's Encrypt is a new entrant in the Certificate Authority ecosystem that offers free and automated certificate signing. It is visionary in its commitment to Certificate Transparency. In this paper, we shed light on the adoption patterns of Let's Encrypt "in the wild" and inform the future design and deployment of this exciting development in the security landscape. We analyze acquisition patterns of certificates as well as their usage and deployment trends in the real world. To this end, we analyze data from Certificate Transparency Logs containing records of more then 18 million certificates. We also leverage other sources like Censys, Alexa's historic records, Geolocation databases, and VirusTotal. We also perform active HTTPS measurements on the domains owning Let's Encrypt certificates. Our analysis of certificate acquisition shows that (1) the impact of Let's Encrypt is particularly visible in Western Europe; (2) Let's Encrypt has the potential to democratize HTTPS adoption in countries that are recent entrants to Internet adoption; (3) there is anecdotal evidence of popular domains quitting their previously untrustworthy or expensive CAs in order to transition to Let's Encrypt; and (4) there is a "heavy tailed" behavior where a small number of domains acquire a large number of certificates. With respect to usage, we find that: (1) only 54% of domains actually use the Let's Encrypt certificates they have procured; (2) there are many non-trivial incidents of server misconfigurations; and (3) there is early evidence of use of Let's Encrypt certificates for typosquatting and for malware-laden sites.