Please review https://forums.gentoo.org/viewtopic-p-8247330.html#8247330 all info inside , workaround tested. As recommended "Please rebuild dev-libs/openssl with USE=-bindist, then try again. If that helps, please file a bug to have the ebuild enforce this requirement"
Thank you for the report. Please recompile and *attach* the logfiles and paste the emerge info as described on https://wiki.gentoo.org/wiki/Attach_the_logs_to_the_bug_ticket Please reopen this ticket (Status:unconfirmed) afterwards. All information must be in the ticket, not on forums or pastebins.
Created attachment 542560 [details] emerge --info '=dev-python/cryptography-2.2.2-r1::gentoo'
Created attachment 542562 [details] build log
I have the same problem. merging dev-python/cryptography fails with missing #include <openssl/ec.h> Rebuilding OpenSSL with -bindist (and OpenSSH as it depends on OpenSSL with bindist if it has bindist set) fixes it. Please reopen this.