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The validator appears not to be sending TLS SNI: http://en.wikipedia.org/wiki/Server_Name_Indication E.g.: http://validator.w3.org/check?uri=https%3A%2F%2Fwww.mnot.net%2F;No200=1 AFAICT it's using LWP:UserAgent, which uses IO::Socket::SSL, which says: http://search.cpan.org/~sullr/IO-Socket-SSL-1.983/lib/IO/Socket/SSL.pm#SNI_Support .. so you *should* just have to upgrade OpenSSL to fix this (perhaps rebuilding Perl afterwards).