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I am running a vsFTP server using virtual users. I chroot each user to their own personal subdirectory. For ease of use I would like to make my usernames case-insensitive, but I am having some trouble because the server always resolves their chroot directory using the exact casing they enter. Obviously this doesn't work because *NIX filesystems are case-sensitive. Is there a way I can specify a value to be lowercase inside of vsftpd.conf (E.G. ToLower($USER))? This way no matter if a user enters JSMITH or jsmith, they will always be chrooted to jsmith/?

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No, vsftpd doesn't support this. Proftpd can however, handle it by using it's mod_rewrite module. Specifically

<IfModule mod_rewrite.c>
    RewriteEngine on

    RewriteMap lowercase int:tolower
    RewriteCondition %m USER
    RewriteRule (.*) ${lowercase:$1}
</IfModule>

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