You can test OpenSSL 1.1.1 on FreeBSD systems using my testing port. The port can be fetched from my git repo. It hooks into the ports framework:

/etc/make.conf:

DEFAULT_VERSIONS+= ssl=openssl-master

To check what the impact is of switching openssl-devel to 1.1.1, I built the same revision ports tree with both 1.1.0g and 1.1.1.p2. From svn info output:

Last Changed Rev: 464958
Last Changed Date: 2018-03-18 21:59:05 +0000 (Sun, 18 Mar 2018)

In addition to already failing ports with 1.1.0, there were 44 additional failing ports. Listed below

category/port

Problem

Ports Status

Upstream status/Comment

chinese/gimp-help-zh_CN

comms/ncid

comms/qsstv

Missing qt5-network dep?

comms/wsjtx

Missing qt5-network dep?

databases/sqlitebrowser

Missing qt5-network dep?

deskutils/pinot

undeclared identifier 'CRYPTO_NUM_LOCKS'

devel/go-json-rest

devel/liteide

Missing qt5-network dep?

emulators/rpcs3

Missing qt5-network dep?

emulators/virtualbox-ose

undefined reference to symbol `OPENSSL_init_ssl@@OPENSSL_1_1_0'

games/cockatrice

graphics/colmap

no matching function for call to 'sse_sum(m256d)'

graphics/drawpile

Missing qt5-network dep?

irc/dxirc

Missing qt5-network dep?

irc/iroffer-dinoex

korean/gimp-help

lang/modula3

lang/rust

failed to run custom build command for openssl-sys v0.9.23

lang/rust-nightly

failed to run custom build command for openssl-sys v0.9.24

math/amath

math/zimpl

net/libmaia

Missing qt5-network dep?

net/py-qt5-network

Missing qt5-network dep?

net/py-qt5-network@py36

Missing qt5-network dep?

net-im/libqtelegram-ae

member access into incomplete type 'RSA' (aka 'rsa_st')

net-im/qxmpp-qt5

Missing qt5-network dep?

net-im/telegram-desktop

use of undeclared identifier 'AES_ctr128_encrypt'

net-mgmt/seafile-gui

Missing qt5-network dep?

net-p2p/bitcoin

Missing qt5-network dep?

net-p2p/dogecoin

Detected LibreSSL: This is NOT supported, and may break consensus compatibility!

net-p2p/litecoin

Missing qt5-network dep?

net-p2p/qtum

member access into incomplete type 'ECDSA_SIG' (aka 'ECDSA_SIG_st')

security/hitch

expanded from macro 'SSL_CTX_set_tlsext_servername_arg'

security/keepassxc

Missing qt5-network dep?

security/softether

OpenSSL Library Init Failed. (too old?)

security/softhsm2

OpenSSL library has no GOST support

sysutils/sysadm

Missing qt5-network dep?

sysutils/sysadm-client

Missing qt5-network dep?

sysutils/tarsnap-gui

Missing qt5-network dep?

textproc/htmlc

www/qt5-webkit

Missing qt5-network dep?

x11/lumina-core

Missing qt5-network dep?

x11-toolkits/kf5-kxmlgui

Missing qt5-network dep?

x11-toolkits/qt5pas

Missing qt5-network dep?

OpenSSL/1.1.1 (last edited 2018-03-20T20:03:10+0000 by BernardSpil)