-CURRENT has OpenSSL 1.0.2 since r290207 (Oct 2015), which has the same soversion of libcrypto/libssl as the port (was never bumped from 8 when it was updated to 1.0.2), so causes some odd visible breakage (and potentially worse invisible). Additionally, the port makefile checks that the base version isn't greater than the port version; it should probably check >= to catch these cases too...
As far as I know OpenSSL in the base of FreeBSD -CURRENT will be moved, so no port will link to it in the future. The next soversion bump is scheduled for OpneSSL 1.1.0 bsd.openssl.mk sets rpath ( -Wl,-rpath,/usr/local/lib ), to handle the case if the soversion is the same. unless the build system of a port ignores that. OpenSSL 1.0.2 in base and Port should be binary compatible. Do you have any evidence where this goes wrong?
They're actually not binary compatible, since the port has at least MD2 enabled, but base doesn't. This shows up building emulators/virtualbox-ose, which blows up linking being unable to find MD2 bits. Presumably configuring itself against the headers from the ports install, but finally trying to link to base. kBuild: Linking VBoxExtPackHelperApp /usr/ports.work/usr/ports/emulators/virtualbox-ose/work/VirtualBox-4.3.38/out/freebsd.amd64/release/bin/VBoxRT.so: undefined reference to `MD2_Final' /usr/ports.work/usr/ports/emulators/virtualbox-ose/work/VirtualBox-4.3.38/out/freebsd.amd64/release/bin/VBoxRT.so: undefined reference to `MD2_Update' /usr/ports.work/usr/ports/emulators/virtualbox-ose/work/VirtualBox-4.3.38/out/freebsd.amd64/release/bin/VBoxRT.so: undefined reference to `MD2_Init' c++: error: linker command failed with exit code 1 (use -v to see invocation) kmk: *** [/usr/ports.work/usr/ports/emulators/virtualbox-ose/work/VirtualBox-4.3.38/out/freebsd.amd64/release/obj/VBoxExtPackHelperApp/VBoxExtPackHelperApp] Error 1 The failing command: @c++ '-Wl,-rpath,/usr/local/lib/virtualbox' -m64 -o /usr/ports.work/usr/ports/emulators/virtualbox-ose/work/VirtualBox-4.3.38/out/freebsd.amd64/release/obj/VBoxExtPackHelperApp/VBoxExtPackHelperApp /usr/ports.work/usr/ports/emulators/virtualbox-ose/work/VirtualBox-4.3.38/out/freebsd.amd64/release/obj/VBoxExtPackHelperApp/src-helper-apps/VBoxExtPackHelperApp.o /usr/ports.work/usr/ports/emulators/virtualbox-ose/work/VirtualBox-4.3.38/out/freebsd.amd64/release/obj/VBoxExtPackHelperApp/src-all/ExtPackUtil.o -L/usr/local/lib /usr/ports.work/usr/ports/emulators/virtualbox-ose/work/VirtualBox-4.3.38/out/freebsd.amd64/release/bin/VBoxRT.so (this case at least is obvious; I'm a lot more concerned about things that might silently "work"...)
Another that goes wonky in even weirder ways: net/ntp. /usr/local/sbin/ntpd: libcrypto.so.8 => /usr/local/lib/libcrypto.so.8 (0x800e00000) libssl.so.8 => /usr/lib/libssl.so.8 (0x801c62000) /usr/local/sbin/ntptime: libcrypto.so.8 => /lib/libcrypto.so.8 (0x801a00000) libssl.so.8 => /usr/lib/libssl.so.8 (0x801640000) Even if theoretically ports should be doing tricksy overrides to always look in the right direction, I think in practice having the same shlibver is playing with a pretty big fire. Especially on something so security-central.
(In reply to Dirk Meyer from comment #1) > As far as I know OpenSSL in the base of FreeBSD -CURRENT will be moved, > so no port will link to it in the future. It's still public/exposed for 11.0
no longer MAINTAINER
TL;DR: you need to bump devel/openssl's .so version (8 -> 9)
Created attachment 176252 [details] svn diff for security/openssl Bump shlib-version of security/openssl security/openssl-devel Document shlib-version bump in UPDATING
A commit references this bug: Author: brnrd Date: Fri Oct 28 19:49:18 UTC 2016 New revision: 424878 URL: https://svnweb.freebsd.org/changeset/ports/424878 Log: security/openssl: Bump shared library version - Bump shlib version for security/openssl - Bump shlib version for security/openssl-devel - Add instructions to UPDATING PR: 209582 Reported by: Matthew D. Fuller <fullermd@over-yonder.net> MFH: 2016Q4 Changes: head/UPDATING head/security/openssl/version.mk head/security/openssl-devel/version.mk
A commit references this bug: Author: brnrd Date: Fri Oct 28 20:05:49 UTC 2016 New revision: 424879 URL: https://svnweb.freebsd.org/changeset/ports/424879 Log: security/openssl: Bump PORTREVISION - Make sure ports get rebuilt PR: 209582 Reported by: mat Changes: head/security/openssl/Makefile head/security/openssl-devel/Makefile
A commit references this bug: Author: brnrd Date: Fri Oct 28 21:43:03 UTC 2016 New revision: 424886 URL: https://svnweb.freebsd.org/changeset/ports/424886 Log: MFH: r424878 r424879 security/openssl: Bump shared library version - Bump shlib version for security/openssl - Bump shlib version for security/openssl-devel - Bump PORTREVISION - Add instructions to UPDATING PR: 209582 Reported by: Matthew D. Fuller <fullermd@over-yonder.net>, mat Approved by: ports-secteam (feld) Changes: _U branches/2016Q4/ branches/2016Q4/UPDATING branches/2016Q4/security/openssl/Makefile branches/2016Q4/security/openssl/version.mk branches/2016Q4/security/openssl-devel/Makefile branches/2016Q4/security/openssl-devel/version.mk