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Defaults path of Certbot are the following: config: /etc/letsencrypt workdir: /var/letsencrypt/lib logs: /var/letsencrypt/log On Windows, this translate into: config: C:\etc\letsencrypt workdir: C:\var\letsencrypt\lib logs: C:\var\letsencrypt\log As Windows does not follow the standard POSIX filesystem layout, theses paths do not have a lot of sense in this case. This PR sets the following default paths when Certbot is run on Windows: config: C:\Certbot workdir: C:\Certbot\lib logs: C:\Certbot\log Better to decide the default paths for Certbot before users start to run it on Windows, to avoid future migration procedures.